Hydroxyeugenol-properties by Asch

Query Query

Results

Date

67 substances in Reaxys

2017-11-11 21h:16m:40s (EST)

1. Query HO OH

1/124

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Reaxys ID 1911973 View in Reaxys

1/67 CAS Registry Number: 6627-88-9 Chemical Name: 4-allyl-2,6-dimethoxyphenol; 4-allyl-2,6-dimethoxy-phenol; 3-(4-hydroxy-3,5-dimethoxyphenyl)-1-propene; 2,6-dimethoxy-4-(prop-2-enyl)phenol; 2,6-dimethoxy-4-(2-propenyl)phenol; 2,6-dimethoxy-4-allylphenol; 4-methoxyeugenol Linear Structure Formula: CH2CHCH2C6H2(OCH3)2OH Molecular Formula: C11H14O3 Molecular Weight: 194.23 Type of Substance: isocyclic InChI Key: FWMPKHMKIJDEMJ-UHFFFAOYSA-N Note:

HO O

Substance Label (22) Label References 6

Mingyi, Wang; Hongfang, Yang; Anxin, Wu; Xinfu, Pan; Journal of Chemical Research, Synopses; nb. 2; (1999); p. 158 - 159, View in Reaxys; Shirai, Tomohiro; Kumihashi, Kentaro; Sakasai, Mitsuyoshi; Kusuoku, Hiroshi; Shibuya, Yusuke; Ohuchi, Atsushi; ACS Medicinal Chemistry Letters; vol. 8; nb. 7; (2017); p. 715 - 719, View in Reaxys

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys; Frozza, Caroline Olivieri da Silva; Santos, Denis Amilton; Rufatto, Luciane Corbellini; Minetto, Luciane; Scariot, Fernando Joel; Echeverrigaray, Sergio; Pich, Claus Tröger; Moura, Sidnei; Padilha, Francine Ferreira; Borsuk, Sibele; Savegnago, Lucielli; Collares, Tiago; Seixas, Fabiana Kömmling; Dellagostin, Odir; Roesch-Ely, Mariana; Henriques, João Antonio Pêgas; Biomedicine and Pharmacotherapy; vol. 91; (2017); p. 951 - 963, View in Reaxys

Park, Ji-Young; Hwan Lim, Su; Ram Kim, Bo; Jae Jeong, Hyung; Kwon, Hyung-Jun; Song, Gyu-Yong; Bae Ryu, Young; Song Lee, Woo; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 14; (2017); p. 3060 - 3064, View in Reaxys; Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys

Yin, Hui-Shuang; Liu, Hua-Min; Liu, Yu-Lan; Molecules; vol. 22; nb. 6; (2017); Art.No: 890, View in Reaxys

Piotrowska, Dorota G.; Wróblewski, Andrzej E.; Balzarini, Jan; Andrei, Graciela; Schols, Dominique; Snoeck, Robert; Felczak, Aleksandra; Wrońska, Natalia; Lisowska, Katarzyna; Głowacka, Iwona E.; Acta Poloniae Pharmaceutica - Drug Research; vol. 74; nb. 4; (2017); p. 1091 - 1100, View in Reaxys

Mall, Raghao S.; Papalkar, Abhijit S.; Journal of Chemical Research, Miniprint; nb. 10; (2003); p. 1001 1013, View in Reaxys; Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 - 493, View in Reaxys

Curti, Claudio; Zanardi, Franca; Battistini, Lucia; Sartori, Andrea; Rassu, Gloria; Pinna, Luigi; Casiraghi, Giovanni; Journal of Organic Chemistry; vol. 71; nb. 22; (2006); p. 8552 - 8558, View in Reaxys; Boschi, Donatella; Tron, Gian Cesare; Lazzarato, Loretta; Chegaev, Konstantin; Cena, Clara; Di Stilo, Antonella; Giorgis, Marta; Bertinaria, Massimo; Fruttero, Roberta; Gasco, Alberto; Journal of Medicinal Chemistry; vol. 49; nb. 10; (2006); p. 2886 - 2897, View in Reaxys; Gangar, Mukesh; Chouhan, Mangilal; Goyal, Sandeep; Harikrishnan; Chandran; Ittuveetil, Avinash; Nair, Vipin A.; Tetrahedron Letters; vol. 57; nb. 52; (2016); p. 5931 - 5934, View in Reaxys

Patent; Kao Corporation; Shirai, Tomohiro; Kusuoku, Hiroshi; Sakasai, Mitsuyoshi; US2014/329910; (2014); (A1) English, View in Reaxys; Patil, Sagar N.; Tilve, Santosh G.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3371 - 3375, View in Reaxys

Morikawa, Toshio; Hachiman, Ikuko; Matsuo, Kazuhiko; Nishida, Eriko; Ninomiya, Kiyofumi; Hayakawa, Takao; Yoshie, Osamu; Muraoka, Osamu; Nakayama, Takashi; Journal of Natural Products; vol. 79; nb. 8; (2016); p. 2005 - 2013, View in Reaxys

Patent; L'OREAL; DALKO, Maria; HITCE, Julien; (48 pag.); WO2016/92074; (2016); (A1) English, View in Reaxys

Pel, Pisey; Kim, Young-Mi; Chin, Young-Won; Bulletin of the Korean Chemical Society; vol. 36; nb. 1; (2015); p. 384 - 387, View in Reaxys

31; 33; 37

Patent; Washington State University; Yang, Bin; Laskar, Dhrubojyoti Dey; US2015/99868; (2015); (A1) English, View in Reaxys

Wang, Liang; Zhang, Jian; Yi, Xianfeng; Zheng, Anmin; Deng, Feng; Chen, Chunyu; Ji, Yanyan; Liu, Fujian; Meng, Xiangju; Xiao, Feng-Shou; ACS Catalysis; vol. 5; nb. 5; (2015); p. 2727 - 2734, View in Reaxys

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Kim, Sung-Jin; Vassao, Daniel G.; Moinuddin, Syed G.A.; Bedgar, Diana L.; Davin, Laurence B.; Lewis, Norman G.; Archives of Biochemistry and Biophysics; vol. 541; nb. 1; (2014); p. 37 - 46, View in Reaxys

Lee, Ai-Lan; Ley, Steven V; Organic and biomolecular chemistry; vol. 1; nb. 22; (2003); p. 3957 - 3966, View in Reaxys; Flamini, Riccardo; Dalla Vedova, Antonio; Cancian, Davide; Panighel, Annarita; De Rosso, Mirko; Journal of Mass Spectrometry; vol. 42; nb. 5; (2007); p. 641 - 646, View in Reaxys; Toledano, Ana; Serrano, Luis; Labidi, Jalel; Pineda, Antonio; Balu, Alina Mariana; Luque, Rafael; ChemCatChem; vol. 5; nb. 4; (2013); p. 977 - 985, View in Reaxys

VII

Patent; ASSISTANCE PUBLIQUE - HOPITAUX DE PARIS; UNIVERSITE PIERRE ET MARIE CURIE; UNIVERSITE DE STRASBOURG; CHOPPIN, Sabine; COLOBERT, Francoise; HANQUET, Gilles; LEROUX, Frederic; MAHMOUDI, Nassira; MAZIER, Dominique; WO2010/40730; (2010); (A1) English, View in Reaxys

Jing, Xiaobi; Gu, Wenxin; Bie, Pingyan; Ren, Xinfeng; Pan, Xinfu; Synthetic Communications; vol. 31; nb. 6; (2001); p. 861 - 867, View in Reaxys; Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 - 63, View in Reaxys; Jing, Xiao-Bi; Wang, Li; Han, Ying; Shi, Yao-Cheng; Liu, Yong-Hong; Sun, Jing; Journal of the Chinese Chemical Society; vol. 51; nb. 5 A; (2004); p. 1001 - 1004, View in Reaxys; Ren, Xinfeng; She, Xuegong; Peng, Kun; Su, Ying; Xie, Xingang; Pan, Xinfu; Zhang, Hongbin; Journal of the Chinese Chemical Society; vol. 51; nb. 5 A; (2004); p. 969 - 974, View in Reaxys; Rudroff, Florian; Rydz, Joanna; Ogink, Freek H.; Fink, Michael; Mihovilovic, Marko D.; Advanced Synthesis and Catalysis; vol. 349; nb. 8-9; (2007); p. 1436 1444, View in Reaxys

Nagashima; Murakami; Asakawa; Phytochemistry; vol. 51; nb. 8; (1999); p. 1101-l104, View in Reaxys; Ren, Xinfeng; She, Xuegong; Peng, Kun; Su, Ying; Xie, Xingang; Pan, Xinfu; Journal of Chemical Research - Part S; nb. 6; (2003); p. 358 - 359, View in Reaxys

Subst., Table, entry 4

Baxendale, Ian R.; Lee, Ai-Lan; Ley, Steven V.; Synlett; nb. 3; (2002); p. 516 - 518, View in Reaxys

Nolte, Christopher G.; Schauer, James J.; Cass, Glen R.; Simoneit, Bernd R.T.; Environmental Science and Technology; vol. 35; nb. 10; (2001); p. 1912 - 1919, View in Reaxys

Kuerti, Laszlo; Szilagyi, Laszlo; Antus, Sandor; Nogradi, Mihaly; European Journal of Organic Chemistry; nb. 10; (1999); p. 2579 - 2582, View in Reaxys

ADMP

Thompson; Perera; Krol; Bolton; Chemical Research in Toxicology; vol. 8; nb. 3; (1995); p. 323 - 327, View in Reaxys

Patent-Specific Data (3) Location in Patent References Page/Page column

Patent; Kao Corporation; Shirai, Tomohiro; Kusuoku, Hiroshi; Sakasai, Mitsuyoshi; US2014/329910; (2014); (A1) English, View in Reaxys Patent; OAKY NATURAL CO., LTD; WANG, Sung-Ho; WO2005/44247; (2005); (A1) English, View in Reaxys

Claim

Patent; Rhone-Poulenc S. A.; US4138411; (1979); (A1) English, View in Reaxys; Patent; The Procter and Gamble Company; US6500797; (2002); (B1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.471

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Related Structure (1) Related Structure Referenced Com- References pound The constitution 5-ethenyl-1,2,4of the title comtrimethoxybenpound previously zene suggested by: Gradstein, S. R.; Matsuda, R.; Asakawa Y. J. Hattori

Nagashima; Murakami; Asakawa; Phytochemistry; vol. 51; nb. 8; (1999); p. 1101-l104, View in Reaxys

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Botanical Laboratory, 1981, 50, 231 is incorrect. The correct structure is /BRN= 1867648/ Derivative (4) Comment (Derivative)

References

Benzoat: F: 75-76grad

Isogai et al.; Agricultural and Biological Chemistry; vol. 37; (1973); p. 889,894, View in Reaxys

3.5-dinitro-benzoyl derivative (mp: 129-130 degree )

Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys

benzoyl derivative Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 142; (1935); p. 26,31, View in Reaxys (mp: 77 degree ) benzoyl derivative Hahn; Wassmuth; Chemische Berichte; vol. 67; (1934); p. 696,702, View in Reaxys (mp: 76-77 degree ) Melting Point (1) 1 of 1

Melting Point [°C]

28 - 31

Solvent (Melting Point)

methanol

Simpson, Christopher D.; Paulsen, Michael; Dills, Russell L.; Liu, L.-J. Sally; Kalman, David A.; Environmental Science and Technology; vol. 39; nb. 2; (2005); p. 631 - 637, View in Reaxys Boiling Point (5) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

Comment (Boiling References Point)

148 - 150

Li, Guoqing; Li, Zhan; Fang, Xiuhua; Synthetic Communications; vol. 26; nb. 13; (1996); p. 2569 - 2572, View in Reaxys

123 - 125

Pearl; Journal of the American Chemical Society; vol. 70; (1948); p. 1746, View in Reaxys; Coscia et al.; Journal of Organic Chemistry; vol. 26; (1961); p. 5085,5090, View in Reaxys

170 - 171

Hahn; Wassmuth; Chemische Berichte; vol. 67; (1934); p. 696,702, View in Reaxys

168 - 170

Hahn; Wassmuth; Chemische Berichte; vol. 67; (1934); p. 696,702, View in Reaxys

168 - 169

Oel.

Mauthner; Justus Liebigs Annalen der Chemie; vol. 414; (1918); p. 251, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5478

Pearl; Journal of the American Chemical Society; vol. 70; (1948); p. 1746, View in Reaxys

589

Adsorption (MCS) (1) 1 of 1

Description (Adsorption (MCS))

Chemisorption

Lane; Hubbard; Journal of Physical Chemistry; vol. 77; (1973); p. 1411,1414, 1418, View in Reaxys Chromatographic Data (7) Chromatographic Original string data

Location

GC (Gas chromatography)

References Martín, Juan A.; Solla, Alejandro; García-Vallejo, María C.; Gil, Luis; Phytochemistry; vol. 83; (2012); p. 104 - 109, View in Reaxys; Palomero, Felipe; Bertani, Paolo; Fernández De Simón, Brígida; Cadahía, Estrella; Benito, Santiago; Morata, Antonio; SuárezLepe, José A.; Food Chemistry; vol. 171; (2014); p. 212 - 223, View in Reaxys; Zhang; He; Xue; Chu; Mu; RSC Advances; vol. 6; nb. 16; (2016); p. 12850 - 12861, View in Reaxys; Van Erven, Gijs;

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De Visser, Ries; Merkx, Donny W. H.; Strolenberg, Willem; De Gijsel, Peter; Gruppen, Harry; Kabel, Mirjam A.; Analytical Chemistry; vol. 89; nb. 20; (2017); p. 10907 - 10916, View in Reaxys GC (Gas chromatography)

supporting information

Nishiwaki-Akine, Yuri; Watanabe, Takashi; Green Chemistry; vol. 16; nb. 7; (2014); p. 3569 - 3579, View in Reaxys; Deuss, Peter J.; Scott, Martin; Tran, Fanny; Westwood, Nicholas J.; De Vries, Johannes G.; Barta, Katalin; Journal of the American Chemical Society; vol. 137; nb. 23; (2015); p. 7456 - 7467, View in Reaxys; Wang, Yuan-Ying; Ling, Li-Li; Jiang, Hong; Green Chemistry; vol. 18; nb. 14; (2016); p. 4032 - 4041, View in Reaxys; Yin, Hui-Shuang; Liu, Hua-Min; Liu, Yu-Lan; Molecules; vol. 22; nb. 6; (2017); Art.No: 890, View in Reaxys

HPLC (High performance liquid chromatography)

Toledano, Ana; Serrano, Luis; Labidi, Jalel; Pineda, Antonio; Balu, Alina Mariana; Luque, Rafael; ChemCatChem; vol. 5; nb. 4; (2013); p. 977 - 985, View in Reaxys; Pel, Pisey; Kim, Young-Mi; Chin, Young-Won; Bulletin of the Korean Chemical Society; vol. 36; nb. 1; (2015); p. 384 - 387, View in Reaxys; Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 - 493, View in Reaxys

LC (Liquid chromatography)

Barnaba; Dellacassa; Nicolini; Nardin; Malacarne; Larcher; Food Chemistry; vol. 206; (2016); p. 260 - 266, View in Reaxys

GC (Gas chroma- Retention tography) time/min 22.65

Paragraph 0169

Patent; Washington State University; Yang, Bin; Laskar, Dhrubojyoti Dey; US2015/99868; (2015); (A1) English, View in Reaxys

GC (Gas chroma- Retention tography) time/min 23.56

Paragraph 0169

Patent; Washington State University; Yang, Bin; Laskar, Dhrubojyoti Dey; US2015/99868; (2015); (A1) English, View in Reaxys

GC (Gas chroma- Retention tography) time/min 24.47

Paragraph 0169

Patent; Washington State University; Yang, Bin; Laskar, Dhrubojyoti Dey; US2015/99868; (2015); (A1) English, View in Reaxys

Crystal Property Description (6) Colour & Other Location Properties

References

brown

supporting information

colourless

supporting information

Patil, Sagar N.; Tilve, Santosh G.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3371 - 3375, View in Reaxys

yellow

supporting information

Gangar, Mukesh; Chouhan, Mangilal; Goyal, Sandeep; Harikrishnan; Chandran; Ittuveetil, Avinash; Nair, Vipin A.; Tetrahedron Letters; vol. 57; nb. 52; (2016); p. 5931 5934, View in Reaxys

colourless

Page/Page column 29

Patent; L'OREAL; DALKO, Maria; HITCE, Julien; (48 pag.); WO2016/92074; (2016); (A1) English, View in Reaxys

yellow

supporting information

Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L, View in Reaxys

yellow

Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 - 63, View in Reaxys

Further Information (2) Description (Fur- References ther Information) Further information

Hruza et al.; Journal of Agricultural and Food Chemistry; vol. 22; (1974); p. 123,124, View in Reaxys

Further information

Kaneko; Matsui; Agricultural and Biological Chemistry; vol. 32; (1968); p. 995,1000, View in Reaxys

Solubility (MCS) (1) 1 of 1

Comment (Solubility (MCS))

water-soluble

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1 of 26

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Description (NMR Spec- COSY (Correlation Spectroscopy); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 1H

Location

supporting information

Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

6/124

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Solvents (NMR Spectro- d(4)-methanol scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 - 493, View in Reaxys 7 of 26

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 - 493, View in Reaxys 8 of 26

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Patil, Sagar N.; Tilve, Santosh G.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3371 - 3375, View in Reaxys 9 of 26

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Patil, Sagar N.; Tilve, Santosh G.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3371 - 3375, View in Reaxys 10 of 26

Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Patil, Sagar N.; Tilve, Santosh G.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3371 - 3375, View in Reaxys 11 of 26

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

7/124

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Gangar, Mukesh; Chouhan, Mangilal; Goyal, Sandeep; Harikrishnan; Chandran; Ittuveetil, Avinash; Nair, Vipin A.; Tetrahedron Letters; vol. 57; nb. 52; (2016); p. 5931 - 5934, View in Reaxys 12 of 26

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Gangar, Mukesh; Chouhan, Mangilal; Goyal, Sandeep; Harikrishnan; Chandran; Ittuveetil, Avinash; Nair, Vipin A.; Tetrahedron Letters; vol. 57; nb. 52; (2016); p. 5931 - 5934, View in Reaxys 13 of 26

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L, View in Reaxys 14 of 26

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L, View in Reaxys 15 of 26

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Yuan, Hua Jie; Cheng, Yao Yao; Qian, Shan; Xiao, Xiang; Wu, Yong; Chinese Chemical Letters; vol. 21; nb. 2; (2010); p. 127 - 130, View in Reaxys 16 of 26

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Miyase, Toshio; Kuroyanagi, Masanori; Noro, Tadataka; Ueno, Akira; Fukushima, Seigo; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 10; (1985); p. 4445 - 4450, View in Reaxys; Sy, Lai-King; Saunders, Richard M. K.; Brown, Geoffrey D.; Phytochemistry; vol. 44; nb. 6; (1997); p. 1099 - 1108, View in Reaxys; Rudroff, Florian; Rydz, Joanna; Ogink, Freek H.; Fink, Michael; Mihovilovic, Marko D.; Advanced Synthesis and Catalysis; vol. 349; nb. 8-9; (2007); p. 1436 - 1444, View in Reaxys 17 of 26

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Miyase, Toshio; Kuroyanagi, Masanori; Noro, Tadataka; Ueno, Akira; Fukushima, Seigo; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 10; (1985); p. 4445 - 4450, View in Reaxys; Li, Guoqing; Li, Zhan; Fang, Xiuhua; Synthetic Communications; vol. 26; nb. 13; (1996); p. 2569 - 2572, View in Reaxys; Sy, Lai-King; Saunders, Richard M. K.; Brown, Geoffrey D.; Phytochemistry; vol. 44; nb. 6; (1997); p. 1099 - 1108, View in Reaxys; Mingyi, Wang; Hongfang, Yang; Anxin, Wu; Xinfu, Pan; Journal of Chemical Research, Synopses; nb. 2; (1999); p. 158 159, View in Reaxys; Rudroff, Florian; Rydz, Joanna; Ogink, Freek H.; Fink, Michael; Mihovilovic, Marko D.; Advanced Synthesis and Catalysis; vol. 349; nb. 8-9; (2007); p. 1436 - 1444, View in Reaxys 18 of 26

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Ren, Xinfeng; She, Xuegong; Peng, Kun; Su, Ying; Xie, Xingang; Pan, Xinfu; Zhang, Hongbin; Journal of the Chinese Chemical Society; vol. 51; nb. 5 A; (2004); p. 969 - 974, View in Reaxys 19 of 26

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Ren, Xinfeng; She, Xuegong; Peng, Kun; Su, Ying; Xie, Xingang; Pan, Xinfu; Zhang, Hongbin; Journal of the Chinese Chemical Society; vol. 51; nb. 5 A; (2004); p. 969 - 974, View in Reaxys 20 of 26

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Mingyi, Wang; Hongfang, Yang; Anxin, Wu; Xinfu, Pan; Journal of Chemical Research, Synopses; nb. 2; (1999); p. 158 - 159, View in Reaxys 23 of 26

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Miyase, Toshio; Kuroyanagi, Masanori; Noro, Tadataka; Ueno, Akira; Fukushima, Seigo; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 10; (1985); p. 4445 - 4450, View in Reaxys 24 of 26

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Shibuya; Abe; Nakahashi; Kubota; Chemical and Pharmaceutical Bulletin; vol. 26; nb. 9; (1978); p. 2671 - 2673, View in Reaxys; Yamamura,S. et al.; Bulletin of the Chemical Society of Japan; vol. 49; (1976); p. 1940 - 1948, View in Reaxys 26 of 26

Description (NMR Spec- NMR troscopy) Isogai et al.; Agricultural and Biological Chemistry; vol. 37; (1973); p. 889,894, View in Reaxys; Yamamura et al.; Tetrahedron Letters; (1973); p. 4877,4878-4879, View in Reaxys

IR Spectroscopy (8) 1 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Location

supporting information

Patil, Sagar N.; Tilve, Santosh G.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3371 - 3375, View in Reaxys 2 of 8

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L, View in Reaxys

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3 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Yuan, Hua Jie; Cheng, Yao Yao; Qian, Shan; Xiao, Xiang; Wu, Yong; Chinese Chemical Letters; vol. 21; nb. 2; (2010); p. 127 - 130, View in Reaxys 4 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Mingyi, Wang; Hongfang, Yang; Anxin, Wu; Xinfu, Pan; Journal of Chemical Research, Synopses; nb. 2; (1999); p. 158 - 159, View in Reaxys 5 of 8

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3520 - 1460 cm**(-1)

Li, Guoqing; Li, Zhan; Fang, Xiuhua; Synthetic Communications; vol. 26; nb. 13; (1996); p. 2569 - 2572, View in Reaxys 6 of 8

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3550 - 1115 cm**(-1)

Miyase, Toshio; Kuroyanagi, Masanori; Noro, Tadataka; Ueno, Akira; Fukushima, Seigo; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 10; (1985); p. 4445 - 4450, View in Reaxys 7 of 8

Description (IR Spectroscopy)

Bands

Description (IR Spectroscopy)

Isogai et al.; Agricultural and Biological Chemistry; vol. 37; (1973); p. 889,894, View in Reaxys; Yamamura et al.; Tetrahedron Letters; (1973); p. 4877,4878-4879, View in Reaxys Mass Spectrometry (16) Description (Mass Location Spectrometry) electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); spectrum

supporting information

References Park, Ji-Young; Hwan Lim, Su; Ram Kim, Bo; Jae Jeong, Hyung; Kwon, Hyung-Jun; Song, Gyu-Yong; Bae Ryu, Young; Song Lee, Woo; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 14; (2017); p. 3060 - 3064, View in Reaxys

electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); high resolution mass spectrometry (HRMS); spectrum

Frozza, Caroline Olivieri da Silva; Santos, Denis Amilton; Rufatto, Luciane Corbellini; Minetto, Luciane; Scariot, Fernando Joel; Echeverrigaray, Sergio; Pich, Claus Tröger; Moura, Sidnei; Padilha, Francine Ferreira; Borsuk, Sibele; Savegnago, Lucielli; Collares, Tiago; Seixas, Fabiana Kömmling; Dellagostin, Odir; Roesch-Ely, Mariana; Henriques, João Antonio Pêgas; Biomedicine and Pharmacotherapy; vol. 91; (2017); p. 951 - 963, View in Reaxys

gas chromatography mass spectrometry (GCMS); electron impact (EI); spectrum

Van Erven, Gijs; De Visser, Ries; Merkx, Donny W. H.; Strolenberg, Willem; De Gijsel, Peter; Gruppen, Harry; Kabel, Mirjam A.; Analytical Chemistry; vol. 89; nb. 20; (2017); p. 10907 - 10916, View in Reaxys

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gas chromatography mass spectrometry (GCMS); spectrum

Palomero, Felipe; Bertani, Paolo; Fernández De Simón, Brígida; Cadahía, Estrella; Benito, Santiago; Morata, Antonio; Suárez-Lepe, José A.; Food Chemistry; vol. 171; (2014); p. 212 - 223, View in Reaxys; Ohra-Aho, Taina; Niemi, Piritta; Aura, Anna-Marja; Orlandi, Marco; Poutanen, Kaisa; Buchert, Johanna; Tamminen, Tarja; Journal of Agricultural and Food Chemistry; vol. 64; nb. 4; (2016); p. 812 - 820, View in Reaxys

electrospray ionisation (ESI); high resolution mass spectrometry (HRMS); spectrum

Barnaba; Dellacassa; Nicolini; Nardin; Malacarne; Larcher; Food Chemistry; vol. 206; (2016); p. 260 - 266, View in Reaxys

time-of-flight mass spectra (TOFMS); high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 493, View in Reaxys

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Gangar, Mukesh; Chouhan, Mangilal; Goyal, Sandeep; Harikrishnan; Chandran; Ittuveetil, Avinash; Nair, Vipin A.; Tetrahedron Letters; vol. 57; nb. 52; (2016); p. 5931 5934, View in Reaxys

HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

supporting information

Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L, View in Reaxys

ESI (Electrospray ionisation); Spectrum

supporting information

Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L, View in Reaxys

GCMS (Gas chromatography mass spectrometry); CI (Chemical ionization); Spectrum

Rodriguez-Bencomo, Juan J.; Cabrera-Valido, Hector M.; Perez-Trujillo, Juan P.; Cacho, Juan; Food Chemistry; vol. 127; nb. 3; (2011); p. 1153 - 1162, View in Reaxys

EI (Electron impact); Spectrum

Yuan, Hua Jie; Cheng, Yao Yao; Qian, Shan; Xiao, Xiang; Wu, Yong; Chinese Chemical Letters; vol. 21; nb. 2; (2010); p. 127 - 130, View in Reaxys

fragmentation pattern; collisioninduced dissociation; tandem mass spectrometry

Flamini, Riccardo; Dalla Vedova, Antonio; Cancian, Davide; Panighel, Annarita; De Rosso, Mirko; Journal of Mass Spectrometry; vol. 42; nb. 5; (2007); p. 641 - 646, View in Reaxys

spectrum; electron impact (EI)

Shimizu, Jun-ichi; Watanabe, Masazumi; Agricultural and Biological Chemistry; vol. 46; nb. 6; (1982); p. 1447 - 1452, View in Reaxys; Jing, Xiaobi; Gu, Wenxin; Bie, Pingyan; Ren, Xinfeng; Pan, Xinfu; Synthetic Communications; vol. 31; nb. 6; (2001); p. 861 - 867, View in Reaxys; Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 - 63, View in Reaxys; Rudroff, Florian; Rydz, Joanna; Ogink, Freek H.; Fink, Michael; Mihovilovic, Marko D.; Advanced Synthesis and Catalysis; vol. 349; nb. 8-9; (2007); p. 1436 - 1444, View in Reaxys

GCMS (Gas chromatography mass spectrometry); Spectrum

Marques, Gisela; Gutierrez, Ana; Del Rio, Jose C.; Journal of Agricultural and Food Chemistry; vol. 55; nb. 4; (2007); p. 1327 - 1336, View in Reaxys

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spectrum

Miyase, Toshio; Kuroyanagi, Masanori; Noro, Tadataka; Ueno, Akira; Fukushima, Seigo; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 10; (1985); p. 4445 - 4450, View in Reaxys Ciaramitaro,D.; Steelink,C.; Phytochemistry (Elsevier); vol. 14; (1975); p. 543 - 552, View in Reaxys; Hruza et al.; Journal of Agricultural and Food Chemistry; vol. 22; (1974); p. 123,124, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

dioxane

Comment (UV/VIS Spectroscopy)

230 - 330 nm

Pearl; Journal of the American Chemical Society; vol. 70; (1948); p. 1746, View in Reaxys Ecotoxicology (1) 1 of 1

Effect (Ecotoxicology)

toxicity to invertebrates

Species or Test-System (Ecotoxicology)

brine shrimp

Method (Ecotoxicology)

brine shrimp lethality test

Type (Ecotoxicology)

LC50

Value of Type (Ecotoxicology)

> 100 mg/l

Huang, Jian-Mei; Nakade, Kousuke; Kondo, Mamiko; Yang, Chun-Shu; Fukuyama, Yoshiyasu; Chemical and Pharmaceutical Bulletin; vol. 50; nb. 1; (2002); p. 133 - 136, View in Reaxys Exposure Assessment (1) Exposure Sources presence in air

References

emissions from burning wood

Nilsson, Maritha; Ingemarsson, Asa; Pedersen, Joergen R.; Olsson, Jim O.; Chemosphere; vol. 38; nb. 7; (1999); p. 1469 - 1479, View in Reaxys

Concentration in the Environment (7) 1 of 7

Media (Concentration in the Environment)

smoke

Location

Research Triangle Park, North Carolina

Contamination Concentration

0.26 μg mg-1 PM2.5

Method, Remarks (Concentration in the Environment)

PM2.5 samples collected from smoke during combustion of wheat (Triticum aestivum L.) stubble in chamber experiment using low volume sampler; summer 2004 at U.S. EPA test burn facility; extracted by sonication; GC-MS in SIM; table

Jimenez, Jorge R.; Claiborn, Candis S.; Dhammapaia, Ranil S.; Simpson, Christopher D.; Environmental Science and Technology; vol. 41; nb. 22; (2007); p. 7824 - 7829, View in Reaxys 2 of 7

Media (Concentration in the Environment)

smoke

Location

eastern Washington and northern Idaho

Contamination Concentration

0.03 μg mg-1 PM2.5

Method, Remarks (Concentration in the Environment)

PM2.5 samples collected from smoke during combustion of wheat (Triticum aestivum L.) stubble in field experiment using low volume sampler; fall 2004 and spring 2005; extracted by sonication; GC-MS in SIM; table

Jimenez, Jorge R.; Claiborn, Candis S.; Dhammapaia, Ranil S.; Simpson, Christopher D.; Environmental Science and Technology; vol. 41; nb. 22; (2007); p. 7824 - 7829, View in Reaxys 3 of 7

Media (Concentration in the Environment)

smoke

Location

Research Triangle Park, North Carolina

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Contamination Concentration

0.10 μg mg-1 PM2.5

Method, Remarks (Concentration in the Environment)

PM2.5 samples collected from smoke during combustion of Kentucky bluegrass (Poa pratensis L.) stubble in chamber experiment using low volume sampler; summer 2004 at U.S. EPA test burn facility; extracted by sonication; GC-MS in SIM; table

Jimenez, Jorge R.; Claiborn, Candis S.; Dhammapaia, Ranil S.; Simpson, Christopher D.; Environmental Science and Technology; vol. 41; nb. 22; (2007); p. 7824 - 7829, View in Reaxys 4 of 7

Species (Concentration in the Environment)

eucalyptus

Contamination Concentration

2.5 mg/kg

Method, Remarks (Concentration in the Environment)

emission rate determined; wood combustion test; fine aerosol samples collected ca. 5 m above the fireplate grate; GC/MS analyses (TMS derivative)

Nolte, Christopher G.; Schauer, James J.; Cass, Glen R.; Simoneit, Bernd R.T.; Environmental Science and Technology; vol. 35; nb. 10; (2001); p. 1912 - 1919, View in Reaxys 5 of 7

Species (Concentration in the Environment)

oak

Contamination Concentration

17 mg/kg

Method, Remarks (Concentration in the Environment)

emission rate determined; wood combustion test; fine aerosol samples collected ca. 5 m above the fireplate grate; GC/MS analyses (TMS derivative)

Nolte, Christopher G.; Schauer, James J.; Cass, Glen R.; Simoneit, Bernd R.T.; Environmental Science and Technology; vol. 35; nb. 10; (2001); p. 1912 - 1919, View in Reaxys 6 of 7

Media (Concentration in the Environment)

pyrolysis liquids

Location

Brazil

Contamination Concentration

0.20 percent

Method, Remarks (Concentration in the Environment)

slow pyrolysis of Eucalyptus grandis wood chips; heating from room temp to 450 deg C; heating rate: 56.3 deg C/h; pyrolysis liquids were trapped from smoke; anal. by GC/MS; yield: 0.09 percent (kg title comp./ton dry wood); conc.: percent (g/L total pyrol. liquids)

Pimenta; Bayona; Garcia; Solanas; Archives of Environmental Contamination and Toxicology; vol. 38; nb. 2; (2000); p. 169 - 175, View in Reaxys 7 of 7

Media (Concentration in the Environment)

burning emission

Location

Southern California, USA

Contamination Concentration

1.98 mg/kg burned

Method, Remarks (Concentration in the Environment)

emissions from the combustions of oak wood in residential fireplaces; GC-MS analysis

Rogge, Wolfgang F.; Hildemann, Lynn M.; Mazurek, Monica A.; Cass, Glen R.; Simoneit, Bernd R. T.; Environmental Science and Technology; vol. 32; nb. 1; (1998); p. 13 - 22, View in Reaxys Use (1) Use Pattern insect attractant

References Patent; White, Jeff; Cook, Peter J.; Nkomo, John Edward; Gudz, Nathaniel G.; US2007/292467; (2007); (A1) English, View in Reaxys

Isolation from Natural Product (14) Isolation from References Natural Product seeds of Myristica Park, Ji-Young; Hwan Lim, Su; Ram Kim, Bo; Jae Jeong, Hyung; Kwon, Hyung-Jun; Song, Gyu-Yong; fragrans Bae Ryu, Young; Song Lee, Woo; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 14; (2017); p. 3060 - 3064, View in Reaxys

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from full-ripe fruits Pandey, Renu; Mahar, Rohit; Hasanain, Mohammad; Shukla, Sanjeev K.; Sarkar, Jayanta; Rameshkumar; Kumar, Brijesh; Food Chemistry; vol. 211; (2016); p. 483 - 493, View in Reaxys of M. beddomei, M. fragrans, M. fatua and M. malabaricawere collected from Palode, Thiruvananthapuram, Kerala,India arils of Myristica fragrans; purchased from Tochimoto Tenkaido Co., Ltd. (Osaka, Japan), cultivated in Indonesia

barks of Cinnamomum cambodianum Lecomte (Lauraceae); purchased at Ourousey Market, Phnom Penh, Cambodia, 2008

Pel, Pisey; Kim, Young-Mi; Chin, Young-Won; Bulletin of the Korean Chemical Society; vol. 36; nb. 1; (2015); p. 384 - 387, View in Reaxys

eucalyptus globulus wood chips

Araya, Fabio; Troncoso, Eduardo; Mendonça, Regis Teixeira; Freer, Juanita; Rencoret, Jorge; Del Río, José Carlos; Journal of the Chilean Chemical Society; vol. 60; nb. 2; (2015); p. 2954 - 2960, View in Reaxys

stems and leaves Liu, Ji-Feng; Jiang, Zhi-Yong; Geng, Chang-An; Zou, Xiao-Bin; Shi, Yao; Ma, Yun-Bao; Zhang, Xueof Illicium simonsii Mei; Chen, Ji-Jun; Planta Medica; vol. 76; nb. 13; (2010); p. 1464 - 1467, View in Reaxys Maxim.; collected in Kunming, Yunnan province, China fresh stems of Cocculus orbiculatus from the Country folkloric medicine store, Kaohsiung, Taiwan

Chang, Fang-Rong; Wu, Yang-Chang; Journal of Natural Products; vol. 68; nb. 7; (2005); p. 1056 - 1060, View in Reaxys

ripe fruits of Illicium merrillianum A. C. Smith (Yunnan, China, September 1998)

Huang, Jian-Mei; Nakade, Kousuke; Kondo, Mamiko; Yang, Chun-Shu; Fukuyama, Yoshiyasu; Chemical and Pharmaceutical Bulletin; vol. 50; nb. 1; (2002); p. 133 - 136, View in Reaxys

leaves of Piper aduncum

Parmar, Virinder S.; Jain, Subhash C.; Gupta, Sangita; Talwar, Sangeeta; Rajwanshi, Vivek K.; Kumar, Rajesh; Azim, Abul; Malhotra, Sanjay; Kumar, Naresh; Jain, Rajni; Sharma, Nawal K.; Tyagi, Om D.; Lawrie, Stephen J.; Errington, William; Howarth, Oliwer W.; Olsen, Carl E.; Singh, Sanjay K.; Wengel, Jesper; Phytochemistry; vol. 49; nb. 4; (1998); p. 1069 - 1078, View in Reaxys

Illicium dunniaSy, Lai-King; Saunders, Richard M. K.; Brown, Geoffrey D.; Phytochemistry; vol. 44; nb. 6; (1997); p. num by extraction 1099 - 1108, View in Reaxys with CH2Cl2 in Soxhlet apparatus for 8 h, removal of solvent and chromatograophy Piper aduncum

Parmar, Virinder S.; Jain, Subhash C.; Bisht, Kirpal S.; Jain, Rajni; Taneja, Poonam; Jha, Amitabh; Tyagi, Om D.; Prasad, Ashok K.; Wengel, Jesper; Olsen, Carl E.; Boll, Per M.; Phytochemistry; vol. 46; nb. 4; (1997); p. 597 - 673, View in Reaxys

timber of I. anisa- Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, tum L., collected Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys on Nanjenshan, Pingtung (Taiwan)

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Illicium anisatum

Shibuya; Abe; Nakahashi; Kubota; Chemical and Pharmaceutical Bulletin; vol. 26; nb. 9; (1978); p. 2671 2673, View in Reaxys

aus Samen von Shulgin; Kerlinger; Naturwissenschaften; vol. 51; (1964); p. 360, View in Reaxys; Isogai et al.; Agricultural Myristica fragrans and Biological Chemistry; vol. 37; (1973); p. 889,894, View in Reaxys Medchem (22) 1 of 22

Substance Effect

Toxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Bioassay : brine shrimp lethality test

Biological Species/NCBI Artemia ID Substance RN

1911973View in Reaxys

Substance Name

1453867

Measurement Parameter

LC50

Unit

mg/L

Quantitative value

100

Measurement pX

3.29

Huang, Jian-Mei; Nakade, Kousuke; Kondo, Mamiko; Yang, Chun-Shu; Fukuyama, Yoshiyasu; Chemical and Pharmaceutical Bulletin; vol. 50; nb. 1; (2002); p. 133 - 136, View in Reaxys 2 of 22

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : basophilic leukemia RBL-2H3 cells of ratBioassay : reference comp.: epigallocathechin gallate (50 μmol/l) cells were pretreated with title comp. for 30 min at 37 deg C and stimulated with A23187 (2 μmol/l); effect of title comp. on the inhibition of histamine release was assayed

Substance RN

1911973View in Reaxys

Substance Name

1453867

Substance Dose

50 µM

Qualitative Results

title comp. showed ca. 30% inhibition of histamine release (vs. 28.6% inhibition by reference comp.); figure

Measurement Parameter

Qualitative

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys 3 of 22

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

1911973View in Reaxys

Substance Name

1453867

Qualitative Results

inhibitory activity against lipid oxidation (TBARS assay); inhibitory activity against superoxide production (IC50 = 0.7 mM); no inhibitory activity against hydroxyl radical production (IC50 < 10 mM)

Measurement Parameter

Qualitative

Ogata; Hoshi; Shimotohno; Urano; Endo; JAOCS, Journal of the American Oil Chemists' Society; vol. 74; nb. 5; (1997); p. 557 - 562, View in Reaxys 4 of 22

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Details

Lethal concentration in rat liver slices

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Biological Species/NCBI Rattus norvegicus ID Substance RN

1911973View in Reaxys

Unit

Qualitative value

Quantitative value

2.48

Thompson; Perera; Krol; Bolton; Chemical Research in Toxicology; vol. 8; nb. 3; (1995); p. 323 - 327, View in Reaxys 5 of 22

Target Name

Transient receptor potential cation channel subfamily M member 8 [human]

Target Synonyms

long transient receptor potential channel 6; ltrpc-6; ltrpc6; transient receptor potential cation channel subfamily m member 8; transient receptor potential p8; trp-p8; trpm8; trpp8

Target Uniprot ID

q7z2w7

Target, Subunit, Species Transient receptor potential cation channel subfamily M member 8 [human] Target Mutant/Chimera Details

Transient receptor potential cation channel subfamily M member 8 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Activator

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

HEK293

Substance RN

1911973View in Reaxys

Substance Name

6-methoxyeugenol

Measurement Parameter

EC50

Unit

Quantitative value

113

Measurement pX

6.95

Patent; Kao Corporation; Shirai, Tomohiro; Kusuoku, Hiroshi; Sakasai, Mitsuyoshi; US2014/329910; (2014); (A1) English, View in Reaxys 6 of 22

Target Name

Isocitrate dehydrogenase [NADP] [human]

Target Synonyms

isocitrate dehydrogenase

Target, Subunit, Species Isocitrate dehydrogenase [NADP] [human] Target Mutant/Chimera Details

Isocitrate dehydrogenase [NADP] [human]:Mutated:Substitution

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of mutant human isocitrate dehydrogenase 1 R132H upon incubation with 5 uM compound in 20 mM Tris-Cl, pH 7.5 in presence of 150 uM beta-NADPH using alpha-ketoglutarate as substrate

Substance RN

1911973View in Reaxys

Measurement Parameter

% Inhibition

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7 of 22

Unit

Qualitative value

Quantitative value

103.6

Target Name

Isocitrate dehydrogenase [NADP] [human]

Target Synonyms

isocitrate dehydrogenase

Target, Subunit, Species Isocitrate dehydrogenase [NADP] [human]

8 of 22

Target Mutant/Chimera Details

Isocitrate dehydrogenase [NADP] [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Substance Effect

inhibitory activity

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of human recombinant isocitrate dehydrogenase 1 upon incubation with 5 uM compound in 100 mM Tris-Cl, pH 7.5 in presence of 0.5 mM BETA-NADPH using 2.5 mM ALPHA-KETOGLUTARATE as substrate

Substance RN

1911973View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

100.9

Target Name

Sialidase A [Streptococcus pneumoniae]

Target Synonyms

nana; neuraminidase a; sialidase a

Target Uniprot ID

p62575

Target PDB ID

2vvz; 2ya4; 2ya5; 2ya6; 2ya7; 2ya8; 4c1x; 4zxk

Target, Subunit, Species Sialidase A [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase A [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

1911973View in Reaxys

Substance Name

methoxyeugenol

Substance Dose

<= 200 μM

Measurement Parameter

Unit

μM

Quantitative value

4.2

Measurement pX

5.38

Concomitants: Compound RN

25467977

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Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Target Name

Sialidase C [Streptococcus pneumoniae]

Target Synonyms

sialidase c

Target, Subunit, Species Sialidase C [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase C [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

1911973View in Reaxys

Substance Name

methoxyeugenol

Substance Dose

<= 200 μM

Measurement Parameter

IC50

Unit

μM

Quantitative value

33.6

Measurement pX

4.47

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Target Name

Sialidase C [Streptococcus pneumoniae]

Target Synonyms

sialidase c

Target, Subunit, Species Sialidase C [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase C [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

1911973View in Reaxys

Substance Name

methoxyeugenol

Substance Dose

<= 200 μM

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Measurement Parameter

Unit

μM

Quantitative value

30.2

Measurement pX

4.52

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Target Name

Sialidase A [Streptococcus pneumoniae]

Target Synonyms

nana; neuraminidase a; sialidase a

Target Uniprot ID

p62575

Target PDB ID

2vvz; 2ya4; 2ya5; 2ya6; 2ya7; 2ya8; 4c1x; 4zxk

Target, Subunit, Species Sialidase A [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase A [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

1911973View in Reaxys

Substance Name

methoxyeugenol

Substance Dose

<= 200 μM

Measurement Parameter

IC50

Unit

μM

Quantitative value

6.9

Measurement pX

5.16

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Target Name

Sialidase B [Streptococcus pneumoniae]

Target Synonyms

sialidase b

Target, Subunit, Species Sialidase B [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase B [Streptococcus pneumoniae]:Wild

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Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

1911973View in Reaxys

Substance Name

methoxyeugenol

Substance Dose

<= 200 μM

Measurement Parameter

IC50

Unit

μM

Quantitative value

77.6

Measurement pX

4.11

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

MCF-7 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Qualitative value

Low

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 14 of 22

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

RT-112 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Qualitative value

Low

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 15 of 22

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

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Cells/Cell Lines

EJ-28 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Qualitative value

Low

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 16 of 22

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

PC-3 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Qualitative value

Low

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 17 of 22

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

HSC-4 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Qualitative value

Low

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 18 of 22

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

Hep-G2 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Qualitative value

Low

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 19 of 22

Substance Effect

Cytotoxic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

HMEC cell line

Substance RN

1911973View in Reaxys

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Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Qualitative value

Low

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 20 of 22

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

MDA-MB-231 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

50 μM

Measurement Parameter

% Inhibition

Qualitative value

Low

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 21 of 22

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

MDA-MB-231 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

5 - 50 μM

Measurement Parameter

IC20

Unit

μM

Quantitative value

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys 22 of 22

Substance Effect

Antineoplastic

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

MDA-MB-231 cell line

Substance RN

1911973View in Reaxys

Substance Name

4-allyl-2,6-dimethoxyphenol

Substance Dose

48 μM

Measurement Parameter

% Migration

Unit

Quantitative value

Liew, Su Ki; Azmi, Mohamad Nurul; In, Lionel L. A.; Awang, Khalijah; Nagoor, Noor Hasima; Drug Design, Development and Therapy; vol. 11; (2017); p. 2763 - 2776, View in Reaxys

Reaxys ID 30905466 View in Reaxys

2/67

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Chemical Name: zinc oxide eugenol base; zinc oxide eugenol Linear Structure Formula: C10H12O2*O(2-)*Zn(2+) Molecular Formula: C10H12O2*O*Zn Molecular Weight: 245.593 InChI Key: YBTQRZBBLJRNOC-UHFFFAOYSA-N Note:

HO Zn 2+ O

O2-

Druglikeness (1) 1 of 1

LogP

2.556

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Reaxys ID 2084755 View in Reaxys

3/67 CAS Registry Number: 13677-76-4 Chemical Name: 2-allyl-5-methoxyphenol; 4-allyl-3-hydroxy-1methoxybenzene; 2-hydroxy-4-methoxyallylbenzene; 5-methoxy-2-allylphenol; 6-allyl-3-methoxyphenol; Methyl-(3-hydroxy-4-allyl-phenyl)-aether; 2-Hydroxy-4-methoxy-1-allyl-benzol Linear Structure Formula: C10H12O2 Molecular Formula: C10H12O2 Molecular Weight: 164.204 Type of Substance: isocyclic InChI Key: MKJJSXMKFUCBAM-UHFFFAOYSA-N Note:

HO O

Substance Label (17) Label References 4c

Hemelaere, Rémy; Carreaux, François; Carboni, Bertrand; European Journal of Organic Chemistry; vol. 2015; nb. 11; (2015); p. 2470 - 2481, View in Reaxys

4bx {1}

Patent; Simon Fraser University; US2010/190865; (2010); (A1) English, View in Reaxys

4b%x&{1}

Patent; Simon Fraser University; The University of British Columbia; US2010/160451; (2010); (A1) English, View in Reaxys

Ito, Fumihiro; Fusegi, Keiko; Kumamoto, Takuya; Ishikawa, Tsutomu; Synthesis; nb. 12; (2007); p. 1785 - 1796, View in Reaxys

2f'

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys

IIIb

Jimenez-Gonzalez, Leticia; Garcia-Munoz, Sergio; Alvarez-Corral, Miriam; Munoz-Dorado, Manuel; Rodriguez-Garcia, Ignacio; Chemistry - A European Journal; vol. 12; nb. 34; (2006); p. 8762 - 8769, View in Reaxys

2, R = OMe

Han, Xinxin; Armstrong, Daniel W.; Organic Letters; vol. 7; nb. 19; (2005); p. 4205 - 4208, View in Reaxys

4P-B, R1=OCH3, R6=H

11, X=OCH3

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys

7 (R=CH3)

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys

XIII

Denisenko, V. I.; Mirzoyan, R. G.; Terent'ev, P. B.; Agavelyan, E. S.; Khudoyan, G. G.; Matevosyan, R. O.; Journal of Organic Chemistry USSR (English Translation); vol. 20; nb. 2; (1984); p. 291 - 294; Zhurnal Organicheskoi Khimii; vol. 20; nb. 2; (1984); p. 327 - 330, View in Reaxys

24/124

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Buckle; Outred; Rockell; Smith; Spicer; Journal of Medicinal Chemistry; vol. 26; nb. 2; (1983); p. 251 254, View in Reaxys

3ca

Bigi, Franca; Casiraghi, Giovanni; Casnati, Giuseppe; Sartori, Giovanni; Synthesis; nb. 4; (1981); p. 310 - 312, View in Reaxys

3, R1=H, R2=OMe

Bruce, J. Malcolm; Roshan-Ali, Yusuf; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2677 - 2679, View in Reaxys

Aglykon 4-OH

Higuchi,R.; Donnelly,D.M.X.; Phytochemistry (Elsevier); vol. 16; (1977); p. 1587 - 1590, View in Reaxys

Borgulya,J. et al.; Helvetica Chimica Acta; vol. 56; nb. 1; (1973); p. 14 - 75, View in Reaxys

VIII

Houry,S. et al.; Israel Journal of Chemistry; vol. 11; (1973); p. 805 - 817, View in Reaxys

Patent-Specific Data (2) References Patent; Simon Fraser University; US2010/190865; (2010); (A1) English, View in Reaxys Patent; Simon Fraser University; The University of British Columbia; US2010/160451; (2010); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

2.613

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Related Structure (1) Related Structure Referenced Com- References pound The author has doubts about the constitution/ configuration of the title compound. The following alternatives are discussed/ proposed: /BRN= 2327881/ Boiling Point (4) Boiling Point [°C]

4-allyl-3-methoxy- Higuchi,R.; Donnelly,D.M.X.; Phytochemistry (Elsevier); vol. 16; (1977); p. 1587 - 1590, phenol View in Reaxys

Pressure (Boiling Point) [Torr]

References

140 - 141

Bigi, Franca; Casiraghi, Giovanni; Casnati, Giuseppe; Sartori, Giovanni; Synthesis; nb. 4; (1981); p. 310 - 312, View in Reaxys

129 - 131

Nikiforowa; Mel'kanowizaja; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 144,138, View in Reaxys

114

Takahashi; Senda; Yakugaku Zasshi; vol. 69; (1949); p. 498; Acta Sch. med. Univ. Kioto; vol. 27; (1949); p. 34,39, View in Reaxys; Takahashi; Senda; Acta Sch. med. Univ. Kioto; vol. 27; (1949); p. 34,40, View in Reaxys

143 - 144

Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 102; (1921); p. 42, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.55

Nikiforowa; Mel'kanowizaja; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 144,138, View in Reaxys

589

Density (1)

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1 of 1

Density [g·cm-3]

1.08

Reference Temperature [°C]

Measurement Temperature [°C]

Nikiforowa; Mel'kanowizaja; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 144,138, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties colourless

supporting information

yellow

References Hemelaere, Rémy; Carreaux, François; Carboni, Bertrand; European Journal of Organic Chemistry; vol. 2015; nb. 11; (2015); p. 2470 - 2481, View in Reaxys Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys

Electrochemical Behaviour (1) Description (Elec- References trochemical Behaviour) Electrolytic dissociation / protonation equilibrium

Houry,S. et al.; Israel Journal of Chemistry; vol. 11; (1973); p. 805 - 817, View in Reaxys

NMR Spectroscopy (19) 1 of 19

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Hemelaere, Rémy; Carreaux, François; Carboni, Bertrand; European Journal of Organic Chemistry; vol. 2015; nb. 11; (2015); p. 2470 - 2481, View in Reaxys 2 of 19

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Hemelaere, Rémy; Carreaux, François; Carboni, Bertrand; European Journal of Organic Chemistry; vol. 2015; nb. 11; (2015); p. 2470 - 2481, View in Reaxys 3 of 19

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys

26/124

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4 of 19

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys 5 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys 6 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys 7 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Han, Xinxin; Armstrong, Daniel W.; Organic Letters; vol. 7; nb. 19; (2005); p. 4205 - 4208, View in Reaxys; Jimenez-Gonzalez, Leticia; Garcia-Munoz, Sergio; Alvarez-Corral, Miriam; Munoz-Dorado, Manuel; RodriguezGarcia, Ignacio; Chemistry - A European Journal; vol. 12; nb. 34; (2006); p. 8762 - 8769, View in Reaxys 8 of 19

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy)

27/124

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Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Frequency (NMR Spectroscopy) [MHz]

125.696

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

499.883

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

499.883

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys; Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys 14 of 19

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys

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15 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys 16 of 19

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys 17 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Borgulya,J. et al.; Helvetica Chimica Acta; vol. 56; nb. 1; (1973); p. 14 - 75, View in Reaxys; Higuchi,R.; Donnelly,D.M.X.; Phytochemistry (Elsevier); vol. 16; (1977); p. 1587 - 1590, View in Reaxys; Houry,S. et al.; Israel Journal of Chemistry; vol. 11; (1973); p. 805 - 817, View in Reaxys; Bigi, Franca; Casiraghi, Giovanni; Casnati, Giuseppe; Sartori, Giovanni; Synthesis; nb. 4; (1981); p. 310 - 312, View in Reaxys 18 of 19

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- benzene-d6 scopy) Bruce, J. Malcolm; Roshan-Ali, Yusuf; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); (1981); p. 2677 - 2679, View in Reaxys 19 of 19

Description (NMR Spec- Spin-spin coupling constants troscopy) Comment (NMR Spectroscopy)

1H-1H

Bigi, Franca; Casiraghi, Giovanni; Casnati, Giuseppe; Sartori, Giovanni; Synthesis; nb. 4; (1981); p. 310 - 312, View in Reaxys IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Gozzo, Fabio Cesar; Fernandes, Sergio Antonio; Rodrigues, Denise Cristina; Eberlin, Marcos Nogueira; Marsaioli, Anita Jocelyne; Journal of Organic Chemistry; vol. 68; nb. 14; (2003); p. 5493 - 5499, View in Reaxys; Jimenez-Gonzalez, Leticia; Garcia-Munoz, Sergio; Alvarez-Corral, Miriam; Munoz-Dorado, Manuel; RodriguezGarcia, Ignacio; Chemistry - A European Journal; vol. 12; nb. 34; (2006); p. 8762 - 8769, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3400 - 1180 cm**(-1)

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys

29/124

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3 of 4

Description (IR Spectroscopy)

Kurihara; Kikuchi; Yakugaku Zasshi; vol. 96; (1976); p. 1348,1350; Chem.Abstr.; vol. 86; nb. 60395t, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Bands

Borgulya,J. et al.; Helvetica Chimica Acta; vol. 56; nb. 1; (1973); p. 14 - 75, View in Reaxys Mass Spectrometry (6) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Hemelaere, Rémy; Carreaux, François; Carboni, Bertrand; European Journal of Organic Chemistry; vol. 2015; nb. 11; (2015); p. 2470 - 2481, View in Reaxys

GCMS (Gas chro- Page/Page colmatography mass umn 15 spectrometry)

Patent; Simon Fraser University; US2010/190865; (2010); (A1) English, View in Reaxys

Page/Page column 14

Patent; Simon Fraser University; The University of British Columbia; US2010/160451; (2010); (A1) English, View in Reaxys

spectrum; electron impact (EI)

fragmentation pattern; electron impact (EI); spectrum

UV/VIS Spectroscopy (3) 1 of 3

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

methanol

Comment (UV/VIS Spectroscopy)

Remark: 25 deg C

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys 2 of 3

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

cyclohexane

Comment (UV/VIS Spectroscopy)

Remark: 25 deg C

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys 3 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Higuchi,R.; Donnelly,D.M.X.; Phytochemistry (Elsevier); vol. 16; (1977); p. 1587 - 1590, View in Reaxys Fluorescence Spectroscopy (4) Description (Fluo- Solvent (Fluoresrescence Speccence Spectrotroscopy) scopy)

Temperature (Flu- References orescence Spectroscopy) [°C]

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Spectrum

methanol

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys

Maxima

cyclohexane

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys

Fluorescence excitation spectrum

methanol

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys

Fluorescence excitation spectrum

cyclohexane

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys

Isolation from Natural Product (2) Isolation from References Natural Product Pinus contorta

Higuchi,R.; Donnelly,D.M.X.; Phytochemistry (Elsevier); vol. 16; (1977); p. 1587 - 1590, View in Reaxys

Aus Lamium purpurem L.

Kurihara; Kikuchi; Yakugaku Zasshi; vol. 96; (1976); p. 1348,1350; Chem.Abstr.; vol. 86; nb. 60395t, View in Reaxys

Reaxys ID 1867913 View in Reaxys

4/67 CAS Registry Number: 6738-38-1 Chemical Name: 2-allyl-3-methoxyphenol; 2-allyl-1-hydroxy-3methoxybenzene; 2-allyl-3-methoxy phenol; 2-Allyl-3-methoxyphenol; 3-Methoxy-2-allyl-phenol Linear Structure Formula: C10H12O2 Molecular Formula: C10H12O2 Molecular Weight: 164.204 Type of Substance: isocyclic InChI Key: ZQPSHYPSWNKGNF-UHFFFAOYSA-N Note:

Substance Label (19) Label References 1r

Zhang, Zhenzhong; Kumamoto, Yuhya; Hashiguchi, Taishin; Mamba, Tetsuya; Murayama, Haruno; Yamamoto, Eiji; Ishida, Tamao; Honma, Tetsuo; Tokunaga, Makoto; ChemSusChem; vol. 10; nb. 17; (2017); p. 3482 - 3489, View in Reaxys

4by {1}

Patent; Simon Fraser University; US2010/190865; (2010); (A1) English, View in Reaxys

4b%y&{1}

Patent; Simon Fraser University; The University of British Columbia; US2010/160451; (2010); (A1) English, View in Reaxys

Ito, Fumihiro; Fusegi, Keiko; Kumamoto, Takuya; Ishikawa, Tsutomu; Synthesis; nb. 12; (2007); p. 1785 - 1796, View in Reaxys

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys

IIId

1, R = OMe

Han, Xinxin; Armstrong, Daniel W.; Organic Letters; vol. 7; nb. 19; (2005); p. 4205 - 4208, View in Reaxys

Meza-Avina, Ma Elena; Ordonez, Mario; Fernandez-Zertuche, Mario; Rodriguez-Fragoso, Lourdes; Reyes-Esparza, Jorge; Martinez De Los Rios-Corsino, Abril A.; Bioorganic and Medicinal Chemistry; vol. 13; nb. 23; (2005); p. 6521 - 6528, View in Reaxys

4P-A, R1=OCH3, R6=H

Wang, Eng-Chi; Hsu, Ming-Kun; Lin, Yu-Li; Huang, Keng-Shiang; Heterocycles; vol. 57; nb. 11; (2002); p. 1997 - 2010, View in Reaxys

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9, X=OCH3

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys

ref. 7, (3)

Stefinovic, Marijan; Snieckus, Victor; Journal of Organic Chemistry; vol. 63; nb. 9; (1998); p. 2808 - 2809, View in Reaxys

interm. to 2c

Zhang, Zhao-Rong; Flachsmann, Felix; Moghaddam, Firouz Matloubi; Rueedi, Peter; Tetrahedron Letters; vol. 35; nb. 14; (1994); p. 2153 - 2156, View in Reaxys

Coelho; Vasconcellos; Simas; Rabi; Costa; Synthesis; nb. 10; (1992); p. 914 - 916, View in Reaxys

6 (R = CH3)

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys

Buckle; Outred; Rockell; Smith; Spicer; Journal of Medicinal Chemistry; vol. 26; nb. 2; (1983); p. 251 254, View in Reaxys

2, R1=H, R2=OMe

Bruce, J. Malcolm; Roshan-Ali, Yusuf; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 2677 - 2679, View in Reaxys

Borgulya,J. et al.; Helvetica Chimica Acta; vol. 56; nb. 1; (1973); p. 14 - 75, View in Reaxys

VII

Revenko; Shamshurin; Izvestiya Akademii Nauk Moldavskoi SSR, Biologicheskie i Khimicheskie Nauki; vol. 11; (1964); p. 98; Chem.Abstr.; vol. 65; nb. 2160e; (1966), View in Reaxys

LogP

2.613

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Derivative (1) Comment (Derivative)

References

4-Nitrobenzoat: F.: 77-78grad

Revenko; Shamshurin; Izvestiya Akademii Nauk Moldavskoi SSR, Biologicheskie i Khimicheskie Nauki; vol. 11; (1964); p. 98; Chem.Abstr.; vol. 65; nb. 2160e; (1966), View in Reaxys

Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

139 - 140

Bigi, Franca; Casiraghi, Giovanni; Casnati, Giuseppe; Sartori, Giovanni; Synthesis; nb. 4; (1981); p. 310 - 312, View in Reaxys

93 - 94

Revenko; Shamshurin; Izvestiya Akademii Nauk Moldavskoi SSR, Biologicheskie i Khimicheskie Nauki; vol. 11; (1964); p. 98; Chem.Abstr.; vol. 65; nb. 2160e; (1966), View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5534

Revenko; Shamshurin; Izvestiya Akademii Nauk Moldavskoi SSR, Biologicheskie i Khimicheskie Nauki; vol. 11; (1964); p. 98; Chem.Abstr.; vol. 65; nb. 2160e; (1966), View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.0935

Measurement Temperature [°C]

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Revenko; Shamshurin; Izvestiya Akademii Nauk Moldavskoi SSR, Biologicheskie i Khimicheskie Nauki; vol. 11; (1964); p. 98; Chem.Abstr.; vol. 65; nb. 2160e; (1966), View in Reaxys Crystal Property Description (2) Colour & Other References Properties yellow

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys

red

NMR Spectroscopy (17) 1 of 17

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys 2 of 17

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys 3 of 17

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys 4 of 17

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Lin, Yung-Lun; Cheng, Jen-Yen; Chu, Yen-Ho; Tetrahedron; vol. 63; nb. 45; (2007); p. 10949 - 10957, View in Reaxys 5 of 17

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Wang, Eng-Chi; Hsu, Ming-Kun; Lin, Yu-Li; Huang, Keng-Shiang; Heterocycles; vol. 57; nb. 11; (2002); p. 1997 2010, View in Reaxys; Meza-Avina, Ma Elena; Ordonez, Mario; Fernandez-Zertuche, Mario; Rodriguez-Fragoso, Lourdes; Reyes-Esparza, Jorge; Martinez De Los Rios-Corsino, Abril A.; Bioorganic and Medicinal Chemistry; vol. 13; nb. 23; (2005); p. 6521 - 6528, View in Reaxys 9 of 17

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

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10 of 17

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Frequency (NMR Spectroscopy) [MHz]

125.696

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

499.883

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

499.883

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Wang, Eng-Chi; Hsu, Ming-Kun; Lin, Yu-Li; Huang, Keng-Shiang; Heterocycles; vol. 57; nb. 11; (2002); p. 1997 2010, View in Reaxys 14 of 17

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys; Coelho; Vasconcellos; Simas; Rabi; Costa; Synthesis; nb. 10; (1992); p. 914 - 916, View in Reaxys 15 of 17

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys; Coelho; Vasconcellos; Simas; Rabi; Costa; Synthesis; nb. 10; (1992); p. 914 - 916, View in Reaxys

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16 of 17

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Borgulya,J. et al.; Helvetica Chimica Acta; vol. 56; nb. 1; (1973); p. 14 - 75, View in Reaxys IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Gozzo, Fabio Cesar; Fernandes, Sergio Antonio; Rodrigues, Denise Cristina; Eberlin, Marcos Nogueira; Marsaioli, Anita Jocelyne; Journal of Organic Chemistry; vol. 68; nb. 14; (2003); p. 5493 - 5499, View in Reaxys; Meza-Avina, Ma Elena; Ordonez, Mario; Fernandez-Zertuche, Mario; Rodriguez-Fragoso, Lourdes; Reyes-Esparza, Jorge; Martinez De Los Rios-Corsino, Abril A.; Bioorganic and Medicinal Chemistry; vol. 13; nb. 23; (2005); p. 6521 - 6528, View in Reaxys; Jimenez-Gonzalez, Leticia; Garcia-Munoz, Sergio; Alvarez-Corral, Miriam; Munoz-Dorado, Manuel; Rodriguez-Garcia, Ignacio; Chemistry - A European Journal; vol. 12; nb. 34; (2006); p. 8762 - 8769, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3597 - 1449 cm**(-1)

Coelho; Vasconcellos; Simas; Rabi; Costa; Synthesis; nb. 10; (1992); p. 914 - 916, View in Reaxys 3 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3600 - 1120 cm**(-1)

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Bands

Borgulya,J. et al.; Helvetica Chimica Acta; vol. 56; nb. 1; (1973); p. 14 - 75, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry)

References

GCMS (Gas chro- Page/Page colmatography mass umn 15 spectrometry)

Patent; Simon Fraser University; US2010/190865; (2010); (A1) English, View in Reaxys

Page/Page column 14

Patent; Simon Fraser University; The University of British Columbia; US2010/160451; (2010); (A1) English, View in Reaxys

spectrum; electron impact (EI)

Coelho; Vasconcellos; Simas; Rabi; Costa; Synthesis; nb. 10; (1992); p. 914 - 916, View in Reaxys; Gozzo, Fabio Cesar; Fernandes, Sergio Antonio; Rodrigues, Denise Cristina; Eberlin, Marcos Nogueira; Marsaioli, Anita Jocelyne; Journal of Organic Chemistry; vol. 68; nb. 14; (2003); p. 5493 - 5499, View in Reaxys

36/124

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electron impact (EI); spectrum

Wang, Eng-Chi; Hsu, Ming-Kun; Lin, Yu-Li; Huang, Keng-Shiang; Heterocycles; vol. 57; nb. 11; (2002); p. 1997 - 2010, View in Reaxys

Reaxys ID 2261529 View in Reaxys

5/67 CAS Registry Number: 4055-72-5 Chemical Name: 5-Hydroxyeugenol; 2-hydroxy-3-methoxy-5(2-propenyl)-phenol; 3-methoxy-5-allyl-1,2-benzene-diol; 3-methoxy-5-allyl-1,2-benzenediol; 5-allyl-2,3-dihydroxyanisole; 5hydroxy-eugenol; 5-hydroxyeugenol Linear Structure Formula: C10H12O3 Molecular Formula: C10H12O3 Molecular Weight: 180.203 Type of Substance: isocyclic InChI Key: BHIIRUKUMCZDIB-UHFFFAOYSA-N Note:

OH HO

Substance Label (7) Label References DHA

Al-Malahmeh, Amer J.; Al-Ajlouni, Abdelmajeed; Wesseling, Sebastiaan; Soffers, Ans E. M. F.; Al-Subeihi, Ala’.; Kiwamoto, Reiko; Vervoort, Jacques; Rietjens, Ivonne M. C. M.; Archives of Toxicology; vol. 91; nb. 2; (2017); p. 713 - 734, View in Reaxys

Radwan, Mohamed M.; Tabanca, Nurhayat; Wedge, David E.; Tarawneh, Amer H.; Cutler, Stephen J.; Fitoterapia; vol. 99; nb. 1; (2014); p. 341 - 346, View in Reaxys

Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English, View in Reaxys

Hussein; Hashim; El-Sharawy; Seliem; Linscheid; Lindequist; Nawwar; Phytochemistry; vol. 68; nb. 10; (2007); p. 1464 - 1470, View in Reaxys

1b'

Mamouni; Soukri; Lazar; Akssira; Guillaumet; Tetrahedron Letters; vol. 45; nb. 12; (2004); p. 2631 - 2633, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.579

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.69

Lipinski Number

Veber Number

Derivative (3) Comment (Derivative)

References

monoacetyl deriv- Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys ative (mp: 98 degree to 99 degree ) diacetyl derivative Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys (mp: 75-76 degree )

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dibenzoyl derivative (mp: 110-112 degree ) Boiling Point (6) Boiling Point [°C]

Rao et al.; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 30; (1949); p. 114,118, View in Reaxys

Pressure (Boiling Point) [Torr]

Location

References

176

Page/Page column 19

Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English, View in Reaxys

111

Dallacker,F.; Sluysmans,R.; Monatshefte fuer Chemie; vol. 100; (1969); p. 560 - 566, View in Reaxys

102 - 104

0.2

Kuwatsuka; Casida; Journal of Agricultural and Food Chemistry; vol. 13; (1965); p. 528,529,530, View in Reaxys

112.5 - 115

0.2 - 0.3

Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys

114 - 116

0.2

Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys

176

Rao et al.; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 30; (1949); p. 114,118, View in Reaxys

Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Crystal Property Description (2) Colour & Other Location Properties colourless

Page/Page column 19

yellow

References Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English, View in Reaxys Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 - 63, View in Reaxys; Ahmad, Irshad; Chaudhary, Bashir Ahmad; Janbaz, Khalid Hussain; Uzair, Muhammad; Ashraf, Muhammad; Journal of the Chemical Society of Pakistan; vol. 33; nb. 1; (2011); p. 114 - 117, View in Reaxys

Electrochemical Characteristics (2) 1 of 2

Description (Electrochemical Characteristics)

redox potential

Horner,L.; Geyer,E.; Chemische Berichte; vol. 98; (1965); p. 2016 - 2045, View in Reaxys 2 of 2

Description (Electrochemical Characteristics)

polarographic half-wave potential

Horner,L.; Geyer,E.; Chemische Berichte; vol. 98; (1965); p. 2016 - 2045, View in Reaxys Solubility (MCS) (1) 1 of 1

Location

Page/Page column 19

Comment (Solubility (MCS))

soluble in aqueous sodium hydroxide and aqueous sodium carbonate

Patent; LA GRANGE, Martin James; WO2013/133723; (2013); (A1) English, View in Reaxys NMR Spectroscopy (12) 1 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy)

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Frequency (NMR Spectroscopy) [MHz]

500

Ahmad, Irshad; Chaudhary, Bashir Ahmad; Janbaz, Khalid Hussain; Uzair, Muhammad; Ashraf, Muhammad; Journal of the Chemical Society of Pakistan; vol. 33; nb. 1; (2011); p. 114 - 117, View in Reaxys 2 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

125

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy) [MHz]

500

Hussein; Hashim; El-Sharawy; Seliem; Linscheid; Lindequist; Nawwar; Phytochemistry; vol. 68; nb. 10; (2007); p. 1464 - 1470, View in Reaxys 4 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Hussein; Hashim; El-Sharawy; Seliem; Linscheid; Lindequist; Nawwar; Phytochemistry; vol. 68; nb. 10; (2007); p. 1464 - 1470, View in Reaxys 5 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 - 63, View in Reaxys 7 of 12

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Bezabih, Merhatibeb; Motlhagodi, Selebo; Abegaz, Berhanu M.; Phytochemistry; vol. 46; nb. 6; (1997); p. 1063 1067, View in Reaxys 8 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Bezabih, Merhatibeb; Motlhagodi, Selebo; Abegaz, Berhanu M.; Phytochemistry; vol. 46; nb. 6; (1997); p. 1063 1067, View in Reaxys 9 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Kuang; Shao; Kasai; Ohtani; Tian; Xu; Tanaka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 9; (1991); p. 2440 - 2442, View in Reaxys 10 of 12

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Kuang; Shao; Kasai; Ohtani; Tian; Xu; Tanaka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 9; (1991); p. 2440 - 2442, View in Reaxys 11 of 12

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- tetradeuteriomethanol scopy) Comment (NMR Spectroscopy)

1H-1H.

Kuang; Shao; Kasai; Ohtani; Tian; Xu; Tanaka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 9; (1991); p. 2440 - 2442, View in Reaxys 12 of 12

Description (NMR Spec- NOE troscopy) Kuang; Shao; Kasai; Ohtani; Tian; Xu; Tanaka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 9; (1991); p. 2440 - 2442, View in Reaxys

IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

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Comment (IR Spectroscopy)

3600 - 605 cm**(-1)

Bezabih, Merhatibeb; Motlhagodi, Selebo; Abegaz, Berhanu M.; Phytochemistry; vol. 46; nb. 6; (1997); p. 1063 1067, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Dallacker,F.; Sluysmans,R.; Monatshefte fuer Chemie; vol. 100; (1969); p. 560 - 566, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); EI (Electron impact); Spectrum

Ahmad, Irshad; Chaudhary, Bashir Ahmad; Janbaz, Khalid Hussain; Uzair, Muhammad; Ashraf, Muhammad; Journal of the Chemical Society of Pakistan; vol. 33; nb. 1; (2011); p. 114 - 117, View in Reaxys

spectrum; electron impact (EI)

Bezabih, Merhatibeb; Motlhagodi, Selebo; Abegaz, Berhanu M.; Phytochemistry; vol. 46; nb. 6; (1997); p. 1063 - 1067, View in Reaxys; Jing, Xiaobi; Gu, Wenxin; Bie, Pingyan; Ren, Xinfeng; Pan, Xinfu; Synthetic Communications; vol. 31; nb. 6; (2001); p. 861 - 867, View in Reaxys; Jing, Xiaobi; Gu, Wenxin; Ren, Xinfeng; Bie, Pingyan; Pan, Xinfu; Journal of the Chinese Chemical Society; vol. 48; nb. 1; (2001); p. 59 63, View in Reaxys

UV/VIS Spectroscopy (3) 1 of 3

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 330; 280; 236 VIS) [nm] Log epsilon

3.7; 3.9; 4.1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 272; 278 VIS) [nm] Hussein; Hashim; El-Sharawy; Seliem; Linscheid; Lindequist; Nawwar; Phytochemistry; vol. 68; nb. 10; (2007); p. 1464 - 1470, View in Reaxys 3 of 3

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

CHCl3

Absorption Maxima (UV/ 237; 240 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

16; 32

Bezabih, Merhatibeb; Motlhagodi, Selebo; Abegaz, Berhanu M.; Phytochemistry; vol. 46; nb. 6; (1997); p. 1063 1067, View in Reaxys Isolation from Natural Product (3) Isolation from References Natural Product fruits of Myristica Radwan, Mohamed M.; Tabanca, Nurhayat; Wedge, David E.; Tarawneh, Amer H.; Cutler, Stephen J.; fragrans, nutmeg; Fitoterapia; vol. 99; nb. 1; (2014); p. 341 - 346, View in Reaxys purchased as powders from McCormick & CO., Hunt Valley, MD, USA aerial parts of Vernonia cinerascens Sch. Bip.;

Ahmad, Irshad; Chaudhary, Bashir Ahmad; Janbaz, Khalid Hussain; Uzair, Muhammad; Ashraf, Muhammad; Journal of the Chemical Society of Pakistan; vol. 33; nb. 1; (2011); p. 114 - 117, View in Reaxys

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collected from District Khaniwal, Peruwal roots of Bulbine capitata

Bezabih, Merhatibeb; Motlhagodi, Selebo; Abegaz, Berhanu M.; Phytochemistry; vol. 46; nb. 6; (1997); p. 1063 - 1067, View in Reaxys

Medchem (5) 1 of 5

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

2261529View in Reaxys

Substance Name

273291

Qualitative Results

radical scavenging activity; antioxidative activity in the rabbit erythrocyte membrane ghost system; suppressive effect on pentosidine formation

Measurement Parameter

Qualitative

Oya; Osawa; Kawakishi; Bioscience, Biotechnology and Biochemistry; vol. 61; nb. 2; (1997); p. 263 - 266, View in Reaxys 2 of 5

Target Name

urease

Target Synonyms

afua_1g04560; at1g67550; cnag_05540; cnbl1900; cnh01900; f12b7.10; loc_os12g13270; os12g0234800; osj_35660; spac1952.11c; ure; ure1 (urease); urea amidohydrolase; urease

Target, Subunit, Species urease Target Mutant/Chimera Details

urease:Wild

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Bioassay Details

Effect : enzyme activity Species : not explicitly stated by authors

Substance RN

2261529View in Reaxys

Substance Name

Substance Dose

236 µg/mL

Measurement Parameter

% Inhibition

Unit

Quantitative value

48.4

Measurement pX

2.85

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : radical scavengingBioassay : DPPH radicalDPPH: 1,1-diphenyl-2-picrylhydrazyl

Substance RN

2261529View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µg/mL

Quantitative value

85.05

Measurement pX

3.33

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Target Name

Cytochrome P450 3A4 [human]

Target Synonyms

1,8-cineole 2-exo-monooxygenase; albendazole monooxygenase; albendazole sulfoxidase; cyp3a3; cyp3a4; cypiiia3; cypiiia4; cytochrome p450 3a3; cytochrome p450 3a4; cytochrome p450 hlp; cytochrome p450 nf-25; cytochrome p450-pcn1; nifedipine oxidase; quinine 3-monooxygenase; taurochenodeoxycholate 6-alpha-hydroxylase

Target Uniprot ID

p08684

Target PDB ID

1tqn; 1w0e; 1w0f; 1w0g; 2j0d; 2v0m; 3nxu; 3tjs; 3ua1; 4i3q; 4i4g; 4i4h; 4k9t; 4k9u; 4k9v; 4k9w; 4k9x; 4ny4

Target, Subunit, Species Cytochrome P450 3A4 [human]

5 of 5

Target Mutant/Chimera Details

Cytochrome P450 3A4 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

2261529View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

33.6

Measurement pX

4.47

Metabolite RN

2625776

Metabolite name

6beta-Hydroxytestosterone

Concomitants: Compound RN

24140787; 1915399; 506008; 77911

Concomitants: Compound name

Glucose-6-phosphate; Testosterone; DMSO; NADPH

Concomitants: Compound role

COM; SUB; SLV; COE

Target Name

Cytochrome P450 2C9 [human]

Target Synonyms

(r)-limonene 6-monooxygenase (cytochrome p450 2c9); (s)-limonene 6-monooxygenase (cytochrome p450 2c9); (s)-limonene 7-monooxygenase (cytochrome p450 2c9); cyp2c10; cyp2c9; cypiic9; cytochrome p-450mp; cytochrome p450 2c9; cytochrome p450 mp-4; cytochrome p450 mp-8; cytochrome p450 pb-1; s-mephenytoin 4-hydroxylase (cytochrome p450 2c9)

Target Uniprot ID

p11712

Target PDB ID

1og2; 1og5; 1r9o; 4nz2

Target, Subunit, Species Cytochrome P450 2C9 [human] Target Mutant/Chimera Details

Cytochrome P450 2C9 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

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Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

2261529View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

18.5

Measurement pX

4.73

Metabolite RN

4198042

Metabolite name

4'-Hydroxydiclofenac

Concomitants: Compound RN

2146636; 2146636; 24140787; 506008; 77911

Concomitants: Compound name

Diclofenac; Diclofenac; Glucose-6-phosphate; DMSO; NADPH

Concomitants: Compound role

SUB; SUB; COM; SLV; COE

Reaxys ID 2265191 View in Reaxys

6/67 CAS Registry Number: 32977-07-4 Chemical Name: 2-allyl-3,5-dimethoxyphenol; 2-Allyl-3,5-dimethoxy-phenol; 2-Allyl-3,5-dimethoxyphenol Linear Structure Formula: C11H14O3 Molecular Formula: C11H14O3 Molecular Weight: 194.23 Type of Substance: isocyclic InChI Key: QHEQVNMRWJJAGT-UHFFFAOYSA-N Note:

HO O O

Substance Label (6) Label References 2l

Zhang, Hong-Hao; Wang, Cong-Shuai; Li, Can; Mei, Guang-Jian; Li, Yuxue; Shi, Feng; Angewandte Chemie - International Edition; vol. 56; nb. 1; (2017); p. 116 - 121; Angew. Chem.; vol. 129; nb. 1; (2017); p. 122 - 127,6, View in Reaxys

Hodgetts, Kevin J; Maragkou, Konstantina I; Wallace, Timothy W; Wootton, Robert C.R; Tetrahedron; vol. 57; nb. 31; (2001); p. 6793 - 6804, View in Reaxys

Watanabe, Takumi; Shiraga, Yuichiro; Takeuchi, Tomio; Otsuka, Masami; Umezawa, Kazuo; Heterocycles; vol. 53; nb. 5; (2000); p. 1051 - 1064, View in Reaxys

Reddy, Kalakota S.; Ko, Ok-Hyun; Ho, David; Persons, Paul E.; Cassady, John M.; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3075 - 3078, View in Reaxys

Royer,R. et al.; Bulletin de la Societe Chimique de France; (1971); p. 2072 - 2083, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.528

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

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Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

42 - 43

Solvent (Melting Point)

petroleum ether

Holmes et al.; Journal of the Chemical Society; (1950); p. 2810, View in Reaxys Boiling Point (1) Boiling Point [°C] 175

Pressure (Boiling Point) [Torr]

References

Royer,R. et al.; Bulletin de la Societe Chimique de France; (1971); p. 2072 - 2083, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5487

Royer,R. et al.; Bulletin de la Societe Chimique de France; (1971); p. 2072 - 2083, View in Reaxys

589

Crystal Property Description (1) Colour & Other References Properties yellow

Yamaguchi, Yuki; Akimoto, Ichie; Motegi, Kyoko; Yoshimura, Teruki; Wada, Keiji; Nishizono, Naozumi; Oda, Kazuaki; Heterocycles; vol. 87; nb. 8; (2013); p. 1727 - 1739, View in Reaxys

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- [(2)H6]acetone scopy)

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Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Souris, Caroline; Luparia, Marco; Frebault, Frederic; Audisio, Davide; Fares, Christophe; Goddard, Richard; Maulide, Nuno; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6566 - 6570, View in Reaxys 4 of 6

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- [(2)H6]acetone scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Yamaguchi, Yuki; Akimoto, Ichie; Motegi, Kyoko; Yoshimura, Teruki; Wada, Keiji; Nishizono, Naozumi; Oda, Kazuaki; Heterocycles; vol. 87; nb. 8; (2013); p. 1727 - 1739, View in Reaxys 6 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Yamaguchi, Yuki; Akimoto, Ichie; Motegi, Kyoko; Yoshimura, Teruki; Wada, Keiji; Nishizono, Naozumi; Oda, Kazuaki; Heterocycles; vol. 87; nb. 8; (2013); p. 1727 - 1739, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry)

References

gas chromatogra- supporting inforphy mass specmation trometry (GCMS); electron impact (EI); spectrum

electron impact (EI); spectrum

Yamaguchi, Yuki; Akimoto, Ichie; Motegi, Kyoko; Yoshimura, Teruki; Wada, Keiji; Nishizono, Naozumi; Oda, Kazuaki; Heterocycles; vol. 87; nb. 8; (2013); p. 1727 1739, View in Reaxys

electron impact (EI); high resolution mass spec-

Yamaguchi, Yuki; Akimoto, Ichie; Motegi, Kyoko; Yoshimura, Teruki; Wada, Keiji; Nishizono, Naozumi; Oda, Kazuaki; Heterocycles; vol. 87; nb. 8; (2013); p. 1727 1739, View in Reaxys

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trometry (HRMS); spectrum

Reaxys ID 2327881 View in Reaxys

7/67 CAS Registry Number: 13677-74-2 Chemical Name: 4-allyl-3-methoxyphenol; eugenol; 3-Methoxy-4-allyl-phenol Linear Structure Formula: C10H12O2 Molecular Formula: C10H12O2 Molecular Weight: 164.204 Type of Substance: isocyclic InChI Key: PIVOEPRHDITPMT-UHFFFAOYSA-N Note:

Substance Label (5) Label References 10

Strych, Sebastian; Journot, Guillaume; Pemberton, Ryan P.; Wang, Selina C.; Tantillo, Dean J.; Trauner, Dirk; Angewandte Chemie - International Edition; vol. 54; nb. 17; (2015); p. 5079 - 5083, View in Reaxys

10, X=OCH3

Pincock, Alexandra L.; Pincock, James A.; Stefanova, Roumiana; Journal of the American Chemical Society; vol. 124; nb. 33; (2002); p. 9768 - 9778, View in Reaxys

Swamy; Ilankumaran, Palanichamy; Chandrasekaran, Srinivasan; Synlett; nb. SPEC. ISS.; (1997); p. 513 - 514, View in Reaxys

8 (R = CH3)

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys

Aglykon 2-OH

Higuchi,R.; Donnelly,D.M.X.; Phytochemistry (Elsevier); vol. 16; (1977); p. 1587 - 1590, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.613

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

4-allyl-3-hydroxy-1-methoxybenzene

Higuchi,R.; Donnelly,D.M.X.; Phytochemistry (Elsevier); vol. 16; (1977); p. 1587 - 1590, View in Reaxys

Pressure (Boiling Point) [Torr]

References

Nikiforowa; Mel'kanowizaja; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 144,138, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

47/124

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1.5488

589

Nikiforowa; Mel'kanowizaja; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 144,138, View in Reaxys

Density (1) 1 of 1

Density [g·cm-3]

1.079

Reference Temperature [°C]

Measurement Temperature [°C]

Nikiforowa; Mel'kanowizaja; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 144,138, View in Reaxys Chromatographic Data (1) Chromatographic Location data TLC (Thin layer chromatography)

supporting information

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Strych, Sebastian; Journot, Guillaume; Pemberton, Ryan P.; Wang, Selina C.; Tantillo, Dean J.; Trauner, Dirk; Angewandte Chemie - International Edition; vol. 54; nb. 17; (2015); p. 5079 - 5083, View in Reaxys References Strych, Sebastian; Journot, Guillaume; Pemberton, Ryan P.; Wang, Selina C.; Tantillo, Dean J.; Trauner, Dirk; Angewandte Chemie - International Edition; vol. 54; nb. 17; (2015); p. 5079 - 5083, View in Reaxys

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys 4 of 4

Description (NMR Spec- Spin-spin coupling constants troscopy)

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Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

ATR (attenuated total reflectance); Intensity of IR bands; Bands

Location

supporting information

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3400 - 1160 cm**(-1)

Syamala, M, S.; Ramamurthy, V.; Tetrahedron; vol. 44; nb. 23; (1988); p. 7223 - 7233, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

Medchem (1) 1 of 1

Substance Effect

Sensitizing

Bioassay Category

In Vivo (Animal models)

Bioassay Name

In vivo Measurement

Bioassay Details

Effect : lymph node weight; IL-2 release; CD4 positive cell countBioassay : LLNA - local lymph node assay; LC cells cultured for 48 or 72 h at 37 deg C at 5 percent CO2 in air, then incubated with anti-IL-2 antibody for 30 min, the second anti-IL-2 antibody with peroxidase added; after 1 h developed with 3,3',5,5'-tetramethylbenzidine ex vivo LLNA; 7-9 wk old mice; title comp. applied to both ears of mice for 3 d; 1 d after, auricular lymph nodes (LN) were excised and weighed; LN cells isolated and analyzed for IL-2 release; ELISA; non-specific solvent-induced release was counted

Biological Species/NCBI Mus musculus ID Substance RN

2327881View in Reaxys

Substance Name

1461162

Substance Route of Adm.

cutaneous administration

Qualitative Results

slight increase in LN weight compared to vehicle control; positive IL-2 release: ca. 25 and 15 pg/ml after 48 and 72 h of incubation, resp.; corrected IL-2 index: 3 and 4; slight decrease in the percentage of CD4-positive cells compared to control

Measurement Parameter

Qualitative

Hariya; Hatao; Ichikawa; Food and Chemical Toxicology; vol. 37; nb. 1; (1999); p. 87 - 93, View in Reaxys

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Reaxys ID 7001744 View in Reaxys

8/67 Chemical Name: dehydrodieugenol B; dehydrodieugenol-B Linear Structure Formula: C20H22O4 Molecular Formula: C20H22O4 Molecular Weight: 326.392 Type of Substance: isocyclic InChI Key: IHJFUBOOWFHEMB-UHFFFAOYSA-N Note:

OH O

Substance Label (4) Label References 1

Costa-Silva, Thais Alves Da; Grecco, Simone S.; De Sousa, Fernanda S.; Lago, João Henrique G.; Martins, Euder G. A.; Terrazas, César A.; Varikuti, Sanjay; Owens, Katherine L.; Beverley, Stephen M.; Satoskar, Abhay R.; Tempone, Andre G.; Journal of Natural Products; vol. 78; nb. 4; (2015); p. 653 - 657, View in Reaxys; de Sousa, Fernanda S.; Grecco, Simone S.; Girola, Natalia; Azevedo, Ricardo A.; Figueiredo, Carlos R.; Lago, João Henrique G.; Phytochemistry; vol. 140; (2017); p. 108 - 117, View in Reaxys

Tian, Xinhui; Guo, Xin; Zhuo, Zhiguo; Zeng, Rentao; Fang, Xin; Xu, Xike; Li, Huiliang; Shen, Yunheng; Zhang, Weidong; RSC Advances; vol. 7; nb. 18; (2017); p. 10849 - 10854, View in Reaxys

Dic. OC. D-80024 Kawanishi, Kazuko; Uhara, Yukiko; Hashimoto, Yohei; Phytochemistry (Elsevier); vol. 22; nb. 10; (1983); p. 2277 - 2280, View in Reaxys 2a

Diaz, Aura M. P. de; Gottlieb, Hugo E.; Gottlieb, Otto R.; Phytochemistry (Elsevier); vol. 19; (1980); p. 681 - 682, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.245

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

47.92

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties brown

NMR Spectroscopy (7) 1 of 7

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

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Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3; CCl4 scopy) Diaz, Aura M. P. de; Gottlieb, Hugo E.; Gottlieb, Otto R.; Phytochemistry (Elsevier); vol. 19; (1980); p. 681 - 682, View in Reaxys 7 of 7

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3; CCl4 scopy)

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Comment (NMR Spectroscopy)

1H-1H.

Diaz, Aura M. P. de; Gottlieb, Hugo E.; Gottlieb, Otto R.; Phytochemistry (Elsevier); vol. 19; (1980); p. 681 - 682, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3460 - 921 cm**(-1)

Diaz, Aura M. P. de; Gottlieb, Hugo E.; Gottlieb, Otto R.; Phytochemistry (Elsevier); vol. 19; (1980); p. 681 - 682, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

spectrum

References Costa-Silva, Thais Alves Da; Grecco, Simone S.; De Sousa, Fernanda S.; Lago, João Henrique G.; Martins, Euder G. A.; Terrazas, César A.; Varikuti, Sanjay; Owens, Katherine L.; Beverley, Stephen M.; Satoskar, Abhay R.; Tempone, Andre G.; Journal of Natural Products; vol. 78; nb. 4; (2015); p. 653 - 657, View in Reaxys

Diaz, Aura M. P. de; Gottlieb, Hugo E.; Gottlieb, Otto R.; Phytochemistry (Elsevier); vol. 19; (1980); p. 681 - 682, View in Reaxys

UV/VIS Spectroscopy (2) 1 of 2

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 215; 280 VIS) [nm] Log epsilon

3.2; 2.3

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 285 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

9200

Diaz, Aura M. P. de; Gottlieb, Hugo E.; Gottlieb, Otto R.; Phytochemistry (Elsevier); vol. 19; (1980); p. 681 - 682, View in Reaxys Isolation from Natural Product (6) Isolation from References Natural Product branches and leaves of Illicium burmanicum; collected in Gongshan county, Yunnan province, P. R. China, September 2011

Tian, Xinhui; Guo, Xin; Zhuo, Zhiguo; Zeng, Rentao; Fang, Xin; Xu, Xike; Li, Huiliang; Shen, Yunheng; Zhang, Weidong; RSC Advances; vol. 7; nb. 18; (2017); p. 10849 - 10854, View in Reaxys

twigs of Nectandra leucantha Nees & Mart

de Sousa, Fernanda S.; Grecco, Simone S.; Girola, Natalia; Azevedo, Ricardo A.; Figueiredo, Carlos R.; Lago, João Henrique G.; Phytochemistry; vol. 140; (2017); p. 108 - 117, View in Reaxys

52/124

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(Lauraceae); collected in Cubatao, Sao Paulo, Brazil, in March 2014 twigs of Nectandraleucantha Nees & Mart(Lauraceae) collected inCubatao, Sao Paulo, Brazil, in December 2012

leaves of Ocimum Suzuki, Akiko; Shirota, Osamu; Mori, Kanami; Sekita, Setsuko; Fuchino, Hiroyuki; Takano, Akihito; sanctum L., Tulsi, Kuroyanagi, Masanori; Chemical and Pharmaceutical Bulletin; vol. 57; nb. 3; (2009); p. 245 - 251, purchased at a View in Reaxys market in Kathmandu, Nepal, in August 2003 Virola carinata

Kawanishi, Kazuko; Uhara, Yukiko; Hashimoto, Yohei; Phytochemistry (Elsevier); vol. 22; nb. 10; (1983); p. 2277 - 2280, View in Reaxys

Ocotea cymbarum

Diaz, Aura M. P. de; Gottlieb, Hugo E.; Gottlieb, Otto R.; Phytochemistry (Elsevier); vol. 19; (1980); p. 681 - 682, View in Reaxys

Medchem (5) 1 of 5

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against Leishmania major promastigotes upon incubation for 72 h at 27 degree c by MTT method

Biological Species/NCBI Leishmania major ID Substance RN

7001744View in Reaxys

Measurement Parameter

IC50

Unit

µg/mL

Qualitative value

Quantitative value

16.9

Measurement pX

4.29

Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Selectivity index is the ratio of Cytotoxic concentration of compound against mouse Peritoneal macrophages to that of inhibitory concentration against growth of LEISHMANIA DONOVANI amastigotes

Biological Species/NCBI Mus musculus ID Cells/Cell Lines

macrophage

Substance RN

7001744View in Reaxys

Measurement Parameter

Measurement Object

Cell viability

Qualitative value

Quantitative value

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Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cytotoxic concentration of the compound against mouse Peritoneal macrophages upon incubation for 48 hrs at 37 degree C by MTT ASSAY

Biological Species/NCBI Mus musculus ID Cells/Cell Lines

macrophage

Substance RN

7001744View in Reaxys

Measurement Parameter

CC50

Unit

µM

Measurement Object

Cell viability

Qualitative value

Quantitative value

293.8

Measurement pX

Substance Effect

Anti-Leishmaniasis

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against growth of LEISHMANIA DONOVANI amastigotes upon incubation at 28 degree C for 48 hrs by flow cytometry

Biological Species/NCBI Leishmania donovani ID Substance RN

7001744View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

PARASITE GROWTH

Qualitative value

Quantitative value

26.7

Measurement pX

4.57

Substance Effect

Anti-Leishmaniasis

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against growth of LEISHMANIA DONOVANI promastigotes upon incubation at 28 degree C for 48 hrs by flow cytometry

Biological Species/NCBI Leishmania donovani ID Substance RN

7001744View in Reaxys

Qualitative Results

NA= not active

Measurement Parameter

Qualitative

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Measurement Object

PARASITE GROWTH

Reaxys ID 30836712 View in Reaxys

9/67 Chemical Name: P Eugenol; p-Eugenol Linear Structure Formula: C10H13O2 Molecular Formula: C10H13O2 Molecular Weight: 165.212 InChI Key: SQGWRAVIJAGUTC-UHFFFAOYSA-N Note:

O (v5)

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

9.23

Lipinski Number

Veber Number

Reaxys ID 3267612 View in Reaxys

10/67 CAS Registry Number: 450357-58-1 Chemical Name: 2-hydroxy-3,4-dimethoxyallylbenzene; 6-allyl-2,3-dimethoxyphenol; 2-Hydroxy-3.4-dimethoxy-1-allyl-benzol; 6-Allyl-2,3-dimethoxy-phenol Linear Structure Formula: C11H14O3 Molecular Formula: C11H14O3 Molecular Weight: 194.23 Type of Substance: isocyclic InChI Key: KJYCPOBHNSZMJR-UHFFFAOYSA-N Note:

Substance Label (3) Label References 3a

Hou, Hui-Fang; Peddinti, Rama Krishna; Liao, Chun-Chen; Organic Letters; vol. 4; nb. 15; (2002); p. 2477 - 2480, View in Reaxys

Weinreb,S.M.; Basha,F.Z.; Hibino,S.; Journal of the American Chemical Society; vol. 104; (1982); p. 536, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.26

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

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Derivative (1) Comment (Derivative) 3.5-dinitro-benzoyl derivative (mp: 118-119.5 degree ) Boiling Point (1) Boiling Point [°C] 103 - 105

References Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys

Pressure (Boiling Point) [Torr]

References

0.3

Trikojus; White; Journal of the Chemical Society; (1949); p. 436,437, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Bochicchio, Antonella; Cefola, Rossella; Choppin, Sabine; Colobert, Françoise; Di Noia, Maria Antonietta; Funicello, Maria; Hanquet, Gilles; Pisano, Isabella; Todisco, Simona; Chiummiento, Lucia; Tetrahedron Letters; vol. 57; nb. 36; (2016); p. 4053 - 4055, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

gas chromatogra- supporting inforphy mass specmation trometry (GCMS); electron impact (EI); spectrum

Reaxys ID 5555739 View in Reaxys

11/67 CAS Registry Number: 87893-17-2 Chemical Name: ADPP; 4-allyl-2,6-dimethoxy-3-(3-methyl-2butenyl)phenol; 4-allyl-2,6-dimethoxy-3-prenyl phenol Linear Structure Formula: C16H22O3 Molecular Formula: C16H22O3 Molecular Weight: 262.349 Type of Substance: isocyclic InChI Key: QTDGIJWVHKJACE-UHFFFAOYSA-N

O OH

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Note: Substance Label (2) Label References 6

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys

Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.139

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3540 - 1638 cm**(-1)

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ted in Tokushima, Japan timber of I. anisatum L., collected on Mie Prefectur (Japan)

Yakushijin, Kenichi; Tohshima, Tomoko; Suzuki, Rika; Murata, Hiroyuki; Lu, Sheng-Ten; Furukawa, Hiroshi; Chemical & Pharmaceutical Bulletin; vol. 31; nb. 8; (1983); p. 2879 - 2883, View in Reaxys

Medchem (4) 1 of 4

Substance Effect

Immunostimulant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : basophilic leukemia RBL-2H3 cells of ratBioassay : cells (1E5 cells/well) were stimulated with A23187 (2 μmol/l) in presence of title comp. for 6 h at 37 deg C; inhibition of TNF-α production and/or secretion assayed by ELISA

Substance RN

5555739View in Reaxys

Substance Name

1560074

Substance Dose

50 µM

Qualitative Results

title comp. decreased TNF-α level by 30.0%; figure

Measurement Parameter

Qualitative

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys 2 of 4

Substance Effect

Antiinflammatory

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Substance RN

5555739View in Reaxys

Substance Name

1560074

Substance Dose

1 µM

Measurement Parameter

IC50

Unit

µM

Quantitative value

23.1

Measurement pX

4.64

Matsui, Takuya; Ito, Chihiro; Itoigawa, Masataka; Okada, Tadashi; Furukawa, Hiroshi; Planta Medica; vol. 73; nb. 7; (2007); p. 662 - 665, View in Reaxys 3 of 4

Substance Effect

Neurotrophic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : neurite outgrowthSpecies : SD ratBioassay : primary cultured fetal cortical neuronsneurite length = 249 μm in control (0.5 % ethanol)

Biological Species/NCBI Rattus norvegicus ID Substance RN

5555739View in Reaxys

Substance Name

Substance Dose

1 µM

Qualitative Results

neurite length 400 μm

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Measurement Parameter

Qualitative

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Percent inhibition of A23187-stimulated histamine release from rat basophilic leukemia cells with compound at a concentration of 50 uM

Biological Species/NCBI Rattus norvegicus ID Cells/Cell Lines

B cell lymphoma cell

Substance RN

5555739View in Reaxys

Measurement Parameter

% Inhibition

Unit

Qualitative value

Quantitative value

84.3

Deviation

Gautam, Raju; Jachak, Sanjay M.; Medicinal Research Reviews; vol. 29; nb. 5; (2009); p. 767 - 820, View in Reaxys

Reaxys ID 8142117 View in Reaxys

12/67 CAS Registry Number: 31788-39-3 Chemical Name: 2-methoxy-6-prop-2'-enylbenzene-1,4-diol; 1methoxy-2,5-dihydroxy-3-allylbenzene Linear Structure Formula: C10H12O3 Molecular Formula: C10H12O3 Molecular Weight: 180.203 Type of Substance: isocyclic InChI Key: ZIWAQBRTNFYVGR-UHFFFAOYSA-N Note:

O OH

Substance Label (1) Label References 2h

Yadav; Reddy; Swamy; Tetrahedron Letters; vol. 44; nb. 26; (2003); p. 4861 - 4864, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.939

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.69

Lipinski Number

Veber Number

Reaxys ID 28168841 View in Reaxys

13/67

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Chemical Name: methyldehydrodieugenol B Linear Structure Formula: C21H24O4 Molecular Formula: C21H24O4 Molecular Weight: 340.419 InChI Key: FUMWKJXPNCMONN-UHFFFAOYSA-N Note:

O O

Substance Label (2) Label References 2

Tian, Xinhui; Guo, Xin; Zhuo, Zhiguo; Zeng, Rentao; Fang, Xin; Xu, Xike; Li, Huiliang; Shen, Yunheng; Zhang, Weidong; RSC Advances; vol. 7; nb. 18; (2017); p. 10849 - 10854, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.566

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

36.92

Lipinski Number

Veber Number

Crystal Property Description (2) Colour & Other References Properties colourless

Tian, Xinhui; Guo, Xin; Zhuo, Zhiguo; Zeng, Rentao; Fang, Xin; Xu, Xike; Li, Huiliang; Shen, Yunheng; Zhang, Weidong; RSC Advances; vol. 7; nb. 18; (2017); p. 10849 - 10854, View in Reaxys

yellow

NMR Spectroscopy (7) 1 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Tian, Xinhui; Guo, Xin; Zhuo, Zhiguo; Zeng, Rentao; Fang, Xin; Xu, Xike; Li, Huiliang; Shen, Yunheng; Zhang, Weidong; RSC Advances; vol. 7; nb. 18; (2017); p. 10849 - 10854, View in Reaxys 2 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Tian, Xinhui; Guo, Xin; Zhuo, Zhiguo; Zeng, Rentao; Fang, Xin; Xu, Xike; Li, Huiliang; Shen, Yunheng; Zhang, Weidong; RSC Advances; vol. 7; nb. 18; (2017); p. 10849 - 10854, View in Reaxys

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3 of 7

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C; 1H

Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

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Description (IR Spectroscopy)

Bands; Spectrum

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Costa-Silva, Thais Alves Da; Grecco, Simone S.; De Sousa, Fernanda S.; Lago, João Henrique G.; Martins, Euder G. A.; Terrazas, César A.; Varikuti, Sanjay; Owens, Katherine L.; Beverley, Stephen M.; Satoskar, Abhay R.; Tempone, Andre G.; Journal of Natural Products; vol. 78; nb. 4; (2015); p. 653 - 657, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

electrospray ionisation (ESI); spectrum

Tian, Xinhui; Guo, Xin; Zhuo, Zhiguo; Zeng, Rentao; Fang, Xin; Xu, Xike; Li, Huiliang; Shen, Yunheng; Zhang, Weidong; RSC Advances; vol. 7; nb. 18; (2017); p. 10849 - 10854, View in Reaxys

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 220; 280 VIS) [nm] Log epsilon

3.2; 2.5

Costa-Silva, Thais Alves Da; Grecco, Simone S.; De Sousa, Fernanda S.; Lago, João Henrique G.; Martins, Euder G. A.; Terrazas, César A.; Varikuti, Sanjay; Owens, Katherine L.; Beverley, Stephen M.; Satoskar, Abhay R.; Tempone, Andre G.; Journal of Natural Products; vol. 78; nb. 4; (2015); p. 653 - 657, View in Reaxys Isolation from Natural Product (3) Isolation from References Natural Product branches and leaves of Illicium burmanicum; collected in Gongshan county, Yunnan province, P. R. China, September 2011

Tian, Xinhui; Guo, Xin; Zhuo, Zhiguo; Zeng, Rentao; Fang, Xin; Xu, Xike; Li, Huiliang; Shen, Yunheng; Zhang, Weidong; RSC Advances; vol. 7; nb. 18; (2017); p. 10849 - 10854, View in Reaxys

twigs of Nectande Sousa, Fernanda S.; Grecco, Simone S.; Girola, Natalia; Azevedo, Ricardo A.; Figueiredo, Carlos dra leucantha R.; Lago, João Henrique G.; Phytochemistry; vol. 140; (2017); p. 108 - 117, View in Reaxys Nees & Mart (Lauraceae); collected in Cubatao, Sao Paulo, Brazil, in March 2014 twigs of Nectandraleucantha Nees & Mart(Lauraceae) collected inCubatao, Sao Paulo, Brazil, in December 2012

Medchem (4)

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1 of 4

Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Selectivity index is the ratio of Cytotoxic concentration of compound against mouse Peritoneal macrophages to that of inhibitory concentration against growth of LEISHMANIA DONOVANI amastigotes

Biological Species/NCBI Mus musculus ID Cells/Cell Lines

macrophage

Substance RN

28168841View in Reaxys

Measurement Parameter

Measurement Object

Cell viability

Qualitative value

Quantitative value

6.25

Substance Effect

Cytotoxic

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Cytotoxic concentration of the compound against mouse Peritoneal macrophages upon incubation for 48 hrs at 37 degree C by MTT ASSAY

Biological Species/NCBI Mus musculus ID Cells/Cell Lines

macrophage

Substance RN

28168841View in Reaxys

Measurement Parameter

CC50

Unit

µM

Measurement Object

Cell viability

Qualitative value

Quantitative value

111.2

Measurement pX

3.95

Substance Effect

Anti-Leishmaniasis

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against growth of LEISHMANIA DONOVANI amastigotes upon incubation at 28 degree C for 48 hrs by flow cytometry

Biological Species/NCBI Leishmania donovani ID Substance RN

28168841View in Reaxys

Measurement Parameter

IC50

Unit

µM

Measurement Object

PARASITE GROWTH

Qualitative value

Quantitative value

17.8

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Measurement pX

4.75

Substance Effect

Anti-Leishmaniasis

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of compound against growth of LEISHMANIA DONOVANI promastigotes upon incubation at 28 degree C for 48 hrs by flow cytometry

Biological Species/NCBI Leishmania donovani ID Substance RN

28168841View in Reaxys

Measurement Parameter

Qualitative

Unit

µM

Measurement Object

PARASITE GROWTH

Qualitative value

Quantitative value

111.8

Reaxys ID 1874345 View in Reaxys

14/67 CAS Registry Number: 29445-64-5 Linear Structure Formula: C11H14O3 Molecular Formula: C11H14O3 Molecular Weight: 194.23 Type of Substance: isocyclic InChI Key: PVUBHWCTFDCTSX-UHFFFAOYSA-N Note:

O O

Substance Label (3) Label References 3a'

Hou, Hui-Fang; Peddinti, Rama Krishna; Liao, Chun-Chen; Organic Letters; vol. 4; nb. 15; (2002); p. 2477 - 2480, View in Reaxys

Kurosawa,K. et al.; Phytochemistry (Elsevier); vol. 17; (1978); p. 1389 - 1394, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.26

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Boiling Point (1) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

64/124

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115 - 120

0.03

Kurosawa,K. et al.; Phytochemistry (Elsevier); vol. 17; (1978); p. 1389 - 1394, View in Reaxys

Reaxys ID 2092184 View in Reaxys

15/67 CAS Registry Number: 65632-91-9 Chemical Name: 5-methoxy-3-methyl-2-(prop-2-en-1-yl)phenol; 2-allyl-5-methoxy-3-methylphenol Linear Structure Formula: C11H14O2 Molecular Formula: C11H14O2 Molecular Weight: 178.231 Type of Substance: isocyclic InChI Key: YQYGFEVRZGUNTQ-UHFFFAOYSA-N Note:

HO O

Substance Label (3) Label References 17

Shao, Wenjie; Clive, Derrick L. J.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3211 - 3216, View in Reaxys

Biswas, Bidyut; Sarkar, Debayan; Venkateswaran, Ramanathapuram V.; Tetrahedron; vol. 64; nb. 14; (2008); p. 3212 - 3216, View in Reaxys

XIV

Ahluwalia et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 17; (1979); p. 433,436, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.05

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Crystal Property Description (1) References Ahluwalia et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 17; (1979); p. 433,436, View in Reaxys NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Shao, Wenjie; Clive, Derrick L. J.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3211 - 3216, View in Reaxys 2 of 5

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Shao, Wenjie; Clive, Derrick L. J.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3211 - 3216, View in Reaxys 3 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Biswas, Bidyut; Sarkar, Debayan; Venkateswaran, Ramanathapuram V.; Tetrahedron; vol. 64; nb. 14; (2008); p. 3212 - 3216, View in Reaxys 4 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Biswas, Bidyut; Sarkar, Debayan; Venkateswaran, Ramanathapuram V.; Tetrahedron; vol. 64; nb. 14; (2008); p. 3212 - 3216, View in Reaxys 5 of 5

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

Ahluwalia et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 17; (1979); p. 433,436, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Biswas, Bidyut; Sarkar, Debayan; Venkateswaran, Ramanathapuram V.; Tetrahedron; vol. 64; nb. 14; (2008); p. 3212 - 3216, View in Reaxys

Reaxys ID 3032992 View in Reaxys

16/67 CAS Registry Number: 4647-01-2 Chemical Name: 5-methoxy-2-(1-phenylallyl)phenol; 3-Phenyl-3-(2'-hydroxy-4'-methoxy-phenyl)-propen Linear Structure Formula: C16H16O2 Molecular Formula: C16H16O2 Molecular Weight: 240.302 Type of Substance: isocyclic InChI Key: NTJUVKLOVZNZST-UHFFFAOYSA-N

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Note: Substance Label (2) Label References IIa

Barnes,M.F. et al.; Tetrahedron; vol. 21; (1965); p. 2707 - 2715, View in Reaxys

Phenol X

Eyton et al.; Proceedings of the Chemical Society, London; (1962); p. 301, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.28

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Further Information (1) Description (Fur- References ther Information) Further information

Eyton et al.; Proceedings of the Chemical Society, London; (1962); p. 301, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Miller, Bradley J.; Pieterse, Tanya; Marais, Charlene; Bezuidenhoudt, Barend C.B.; Tetrahedron Letters; vol. 53; nb. 35; (2012); p. 4708 - 4710, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

151

Miller, Bradley J.; Pieterse, Tanya; Marais, Charlene; Bezuidenhoudt, Barend C.B.; Tetrahedron Letters; vol. 53; nb. 35; (2012); p. 4708 - 4710, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Negative ion spectroscopy; Spectrum

Miller, Bradley J.; Pieterse, Tanya; Marais, Charlene; Bezuidenhoudt, Barend C.B.; Tetrahedron Letters; vol. 53; nb. 35; (2012); p. 4708 - 4710, View in Reaxys

Spectrum

Miller, Bradley J.; Pieterse, Tanya; Marais, Charlene; Bezuidenhoudt, Barend C.B.; Tetrahedron Letters; vol. 53; nb. 35; (2012); p. 4708 - 4710, View in Reaxys

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Reaxys ID 7023405 View in Reaxys

17/67 Chemical Name: 5-allyl-2,3-dimethoxyphenol Linear Structure Formula: C11H14O3 Molecular Formula: C11H14O3 Molecular Weight: 194.23 Type of Substance: isocyclic InChI Key: WIGZLFBLFZYGEE-UHFFFAOYSA-N Note:

HO O O

Substance Label (2) Label References 18

Chittimalla, Santhosh Kumar; Kuppusamy, Rajesh; Bandi, Chennakesavulu; Synlett; vol. 25; nb. 14; (2014); p. 1991 - 1996; Art.No: ST-2014-B0420-L, View in Reaxys

Barrero; Mar Herrador; Arteaga; Phytochemistry; vol. 37; nb. 5; (1994); p. 1351 - 1358, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.471

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

300

Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Chittimalla, Santhosh Kumar; Kuppusamy, Rajesh; Bandi, Chennakesavulu; Synlett; vol. 25; nb. 14; (2014); p. 1991 - 1996; Art.No: ST-2014-B0420-L, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

300

Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Chittimalla, Santhosh Kumar; Kuppusamy, Rajesh; Bandi, Chennakesavulu; Synlett; vol. 25; nb. 14; (2014); p. 1991 - 1996; Art.No: ST-2014-B0420-L, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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Solvents (NMR Spectro- CDCl3 scopy) Barrero; Mar Herrador; Arteaga; Phytochemistry; vol. 37; nb. 5; (1994); p. 1351 - 1358, View in Reaxys 4 of 4

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Barrero; Mar Herrador; Arteaga; Phytochemistry; vol. 37; nb. 5; (1994); p. 1351 - 1358, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Barrero; Mar Herrador; Arteaga; Phytochemistry; vol. 37; nb. 5; (1994); p. 1351 - 1358, View in Reaxys

Isolation from Natural Product (1) Isolation from References Natural Product Seseli vayredanum

Barrero; Mar Herrador; Arteaga; Phytochemistry; vol. 37; nb. 5; (1994); p. 1351 - 1358, View in Reaxys

Medchem (2) 1 of 2

Target Name

Cytochrome P450 3A4 [human]

Target Synonyms

Target Uniprot ID

p08684

Target PDB ID

1tqn; 1w0e; 1w0f; 1w0g; 2j0d; 2v0m; 3nxu; 3tjs; 3ua1; 4i3q; 4i4g; 4i4h; 4k9t; 4k9u; 4k9v; 4k9w; 4k9x; 4ny4

Target, Subunit, Species Cytochrome P450 3A4 [human] Target Mutant/Chimera Details

Cytochrome P450 3A4 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

7023405View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

28.2

Measurement pX

4.55

Metabolite RN

2625776

Metabolite name

6beta-Hydroxytestosterone

Concomitants: Compound RN

24140787; 1915399; 506008; 77911

Concomitants: Compound name

Glucose-6-phosphate; Testosterone; DMSO; NADPH

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2 of 2

Concomitants: Compound role

COM; SUB; SLV; COE

Target Name

Cytochrome P450 2C9 [human]

Target Synonyms

Target Uniprot ID

p11712

Target PDB ID

1og2; 1og5; 1r9o; 4nz2

Target, Subunit, Species Cytochrome P450 2C9 [human] Target Mutant/Chimera Details

Cytochrome P450 2C9 [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

Metabolism/Transport

Bioassay Name

Enzymology inhibition

Cells/Cell Lines

Baculovirus-infected insect cell line

Cell Fraction

Microsome

Substance RN

7023405View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

48.6

Measurement pX

4.31

Metabolite RN

4198042

Metabolite name

4'-Hydroxydiclofenac

Concomitants: Compound RN

2146636; 2146636; 24140787; 506008; 77911

Concomitants: Compound name

Diclofenac; Diclofenac; Glucose-6-phosphate; DMSO; NADPH

Concomitants: Compound role

SUB; SUB; COM; SLV; COE

Reaxys ID 7871607 View in Reaxys

18/67 Chemical Name: 3,5-Dimethoxy-4-allylphenol; 4-allyl-3,5-dimethoxyphenol Linear Structure Formula: C11H14O3 Molecular Formula: C11H14O3 Molecular Weight: 194.23 Type of Substance: isocyclic InChI Key: OBJUFRBRWZPXHC-UHFFFAOYSA-N Note:

Substance Label (1) Label References 2p

Lin, Tao-Yan; Wu, Hai-Hong; Feng, Jian-Jun; Zhang, Junliang; Organic Letters; vol. 19; nb. 11; (2017); p. 2897 - 2900, View in Reaxys

Druglikeness (1)

70/124

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1 of 1

LogP

2.528

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

85 - 87

Satoh, Tetsuya; Ikeda, Masahiro; Miura, Masahuri; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 62; nb. 14; (1997); p. 4877 - 4879, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Satoh, Tetsuya; Ikeda, Masahiro; Miura, Masahuri; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 62; nb. 14; (1997); p. 4877 - 4879, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-1H

Satoh, Tetsuya; Ikeda, Masahiro; Miura, Masahuri; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 62; nb. 14; (1997); p. 4877 - 4879, View in Reaxys Ecotoxicology (1) 1 of 1

Effect (Ecotoxicology)

reproductive effects

Endpoint of Effect (Ecotoxicology)

germination

Species or Test-System (Ecotoxicology)

Nicotiana attenuata Torr. ex. Watson, Solanaceae

Concentration (Ecotoxicology)

0.0005 - 0.5 mg/ml

Exposure Period (Ecotoxicology)

Method (Ecotoxicology)

seeds

Further Details (Ecotoxi- 14 light : 10 dark photoperiod with 200 μM/m2/sec PAR; 30 deg C day - 22 deg C night cology) temp. cycle; 9.8 mM aq. KNO3 Results

no stimulation of germination in compared with extract of wood smoke

Baldwin; Staszak-Kozinski; Davidson; Journal of Chemical Ecology; vol. 20; nb. 9; (1994); p. 2345 - 2371, View in Reaxys Medchem (1) 1 of 1

Substance Effect

Reproductive Effect

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

71/124

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Bioassay Details

Effect : germinationTarget : Nicotiana attenuata Torr. ex. Watson, SolanaceaeBioassay : 14 light : 10 dark photoperiod with 200 μM/m2/sec PAR; 30 deg C day - 22 deg C night temp. cycle; 9.8 mM aq. KNO3 seeds

Substance RN

7871607View in Reaxys

Substance Name

1762251

Qualitative Results

no stimulation of germination in compared with extract of wood smoke

Measurement Parameter

Qualitative

Baldwin; Staszak-Kozinski; Davidson; Journal of Chemical Ecology; vol. 20; nb. 9; (1994); p. 2345 - 2371, View in Reaxys

Reaxys ID 6976129 View in Reaxys

19/67 Chemical Name: 3-methylobovatol; 5-allyl-1-(4′-allylphenoxy)-3-methoxyphenol; 4',5-diallyl-2-hydroxy-3-methoxybiphenyl ether Linear Structure Formula: C19H20O3 Molecular Formula: C19H20O3 Molecular Weight: 296.366 Type of Substance: isocyclic InChI Key: KCPHPAFKVWQDHT-UHFFFAOYSA-N Note:

OH O

Substance Label (2) Label References 6

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

Kijjoa, Anake; Pinto, Madalena M. M.; Tantisewie, Bumrung; Herz, Werner; Phytochemistry (Elsevier); vol. 28; nb. 4; (1989); p. 1284 - 1286, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.33

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

72/124

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522-L, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522-L, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Kijjoa, Anake; Pinto, Madalena M. M.; Tantisewie, Bumrung; Herz, Werner; Phytochemistry (Elsevier); vol. 28; nb. 4; (1989); p. 1284 - 1286, View in Reaxys 4 of 4

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Kijjoa, Anake; Pinto, Madalena M. M.; Tantisewie, Bumrung; Herz, Werner; Phytochemistry (Elsevier); vol. 28; nb. 4; (1989); p. 1284 - 1286, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522-L, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3500 - 920 cm**(-1)

Kijjoa, Anake; Pinto, Madalena M. M.; Tantisewie, Bumrung; Herz, Werner; Phytochemistry (Elsevier); vol. 28; nb. 4; (1989); p. 1284 - 1286, View in Reaxys Mass Spectrometry (3) Description (Mass References Spectrometry) electrospray ionisation (ESI); spectrum

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

high resolution mass spectrometry (HRMS); elec-

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

73/124

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trospray ionisation (ESI); spectrum spectrum

Kijjoa, Anake; Pinto, Madalena M. M.; Tantisewie, Bumrung; Herz, Werner; Phytochemistry (Elsevier); vol. 28; nb. 4; (1989); p. 1284 - 1286, View in Reaxys

Isolation from Natural Product (1) Isolation from References Natural Product Magnolia henryi

Kijjoa, Anake; Pinto, Madalena M. M.; Tantisewie, Bumrung; Herz, Werner; Phytochemistry (Elsevier); vol. 28; nb. 4; (1989); p. 1284 - 1286, View in Reaxys

Reaxys ID 8201968 View in Reaxys

20/67 Chemical Name: 3,5-dihydroxyestragole Linear Structure Formula: C10H12O3 Molecular Formula: C10H12O3 Molecular Weight: 180.203 Type of Substance: isocyclic InChI Key: JCQJKRCBKLGOJB-UHFFFAOYSA-N Note:

HO O HO

Substance Label (2) Label References 1

Kitajima, Junichi; Ishikawa, Toru; Tanaka, Yasuko; Ono, Masateru; Ito, Yasuyuki; Nohara, Toshihiro; Chemical and Pharmaceutical Bulletin; vol. 46; nb. 10; (1998); p. 1587 - 1590, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.15

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

74/124

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Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- pyridine-d5 scopy) Kitajima, Junichi; Ishikawa, Toru; Tanaka, Yasuko; Ono, Masateru; Ito, Yasuyuki; Nohara, Toshihiro; Chemical and Pharmaceutical Bulletin; vol. 46; nb. 10; (1998); p. 1587 - 1590, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product seeds of Myristica Park, Ji-Young; Hwan Lim, Su; Ram Kim, Bo; Jae Jeong, Hyung; Kwon, Hyung-Jun; Song, Gyu-Yong; fragrans Bae Ryu, Young; Song Lee, Woo; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 14; (2017); p. 3060 - 3064, View in Reaxys Medchem (6) 1 of 6

Target Name

Sialidase A [Streptococcus pneumoniae]

Target Synonyms

nana; neuraminidase a; sialidase a

Target Uniprot ID

p62575

Target PDB ID

2vvz; 2ya4; 2ya5; 2ya6; 2ya7; 2ya8; 4c1x; 4zxk

Target, Subunit, Species Sialidase A [Streptococcus pneumoniae]

75/124

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Target Mutant/Chimera Details

Sialidase A [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

8201968View in Reaxys

Substance Name

3,5-dihydroxyestragole

Substance Dose

<= 200 μM

Measurement Parameter

Unit

μM

Quantitative value

4.9

Measurement pX

5.31

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Target Name

Sialidase C [Streptococcus pneumoniae]

Target Synonyms

sialidase c

Target, Subunit, Species Sialidase C [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase C [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

8201968View in Reaxys

Substance Name

3,5-dihydroxyestragole

Substance Dose

<= 200 μM

Measurement Parameter

IC50

Unit

μM

Quantitative value

60.5

Measurement pX

4.22

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

76/124

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Concomitants: Compound role

SUB

Target Name

Sialidase B [Streptococcus pneumoniae]

Target Synonyms

sialidase b

Target, Subunit, Species Sialidase B [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase B [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

8201968View in Reaxys

Substance Name

3,5-dihydroxyestragole

Substance Dose

<= 200 μM

Measurement Parameter

Unit

μM

Quantitative value

Measurement pX

4.13

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Target Name

Sialidase C [Streptococcus pneumoniae]

Target Synonyms

sialidase c

Target, Subunit, Species Sialidase C [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase C [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

8201968View in Reaxys

Substance Name

3,5-dihydroxyestragole

Substance Dose

<= 200 μM

Measurement Parameter

77/124

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Unit

μM

Quantitative value

91.8

Measurement pX

4.04

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Target Name

Sialidase A [Streptococcus pneumoniae]

Target Synonyms

nana; neuraminidase a; sialidase a

Target Uniprot ID

p62575

Target PDB ID

2vvz; 2ya4; 2ya5; 2ya6; 2ya7; 2ya8; 4c1x; 4zxk

Target, Subunit, Species Sialidase A [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase A [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

8201968View in Reaxys

Substance Name

3,5-dihydroxyestragole

Substance Dose

<= 200 μM

Measurement Parameter

IC50

Unit

μM

Quantitative value

Measurement pX

5.7

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Target Name

Sialidase B [Streptococcus pneumoniae]

Target Synonyms

sialidase b

Target, Subunit, Species Sialidase B [Streptococcus pneumoniae] Target Mutant/Chimera Details

Sialidase B [Streptococcus pneumoniae]:Wild

Target Species (Bioactivity)

Streptococcus pneumoniae

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Target Transfection

Transfected

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

8201968View in Reaxys

Substance Name

3,5-dihydroxyestragole

Substance Dose

<= 200 μM

Measurement Parameter

IC50

Unit

μM

Quantitative value

27.1

Measurement pX

4.57

Concomitants: Compound RN

25467977

Concomitants: Compound name

4-methylumbelliferyl-α-D-N-acetylneuraminic acid

Concomitants: Compound role

SUB

Reaxys ID 27575416 View in Reaxys

21/67 Chemical Name: 2-allyl-3-methoxy-5-[(E)-styryl]phenol Linear Structure Formula: C18H18O2 Molecular Formula: C18H18O2 Molecular Weight: 266.34 InChI Key: MWXPRUAYEVQJCY-ZHACJKMWSA-N Note:

Substance Label (2) Label References 10h'; 10h

Patent; Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences; LI, Zhuorong; JI, Xingyue; XUE, Situ; ZHENG, Guanghui; LI, Yuhuan; TAO, Peizhen; JIANG, Jiandong; EP2796442; (2014); (A1) English, View in Reaxys

10h'

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys

Patent-Specific Data (2) Location in Patent References Page/Page column

Page/Page column

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.247

H Bond Donors

H Bond Acceptors

79/124

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Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Crystal Property Description (2) Colour & Other Location Properties

References

white

Paragraph 0224

white

Paragraph 0235

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H NMR (400 MHz, CDCl ): 3.24 (d, J = 7.6Hz, 2H), 3.77 (s, 3H), 4.91 (dd, J1 = 16.0Hz, 3 J2 = 12.0Hz, 1H), 4.93 (dd, J1 = 6.4Hz, J2 = 12.0Hz, 1H), 6.30 (m, 1H), 6.32 (s, 1H), 6.38 (s, 1H), 6.82 (d, J = 16.0Hz, 1H), 7.31 (m, 2H), 7.45 (d, J = 7.6Hz, 2H), 7.51 (t, J= 7.6Hz, 2H), 9.88 (s, 1H)

Location

Paragraph 0224

Signals [ppm]

3.24; 3.77; 4.91; 4.93; 6.3; 6.32; 6.38; 6.82; 7.31; 7.45; 7.51; 9.88

Kind of signal

d, J = 7.6Hz, 2H; s, 3H; dd, J1 = 16.0Hz, J2 = 12.0Hz, 1H; dd, J1 = 6.4Hz, J2 = 12.0Hz, 1H; m, 1H; s, 1H; s, 1H; d, J = 16.0Hz, 1H; m, 2H; d, J = 7.6Hz, 2H; t, J= 7.6Hz, 2H; s, 1H

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H NMR (400 MHz, CDCl ): 3.24 (d, J=7.6 Hz, 2H), 3.77 (s, 3H), 4.91 (dd, J1=16.0 Hz, 3 J2=12.0 Hz, 1H), 4.93 (dd, J1=6.4 Hz, J2=12.0 Hz, 1H), 6.30 (m, 1H), 6.32 (s, 1H), 6.38 (s, 1H), 6.82 (d, J=16.0 Hz, 1H), 7.31 (m, 2H), 7.45 (d, J=7.6 Hz, 2H), 7.51 (t, J=7.6 Hz, 2H), 9.88 (s, 1H)

Location

Paragraph 0235

Signals [ppm]

3.24; 3.77; 4.91; 4.93; 6.3; 6.32; 6.38; 6.82; 7.31; 7.45; 7.51; 9.88

Kind of signal

d, J=7.6 Hz, 2H; s, 3H; dd, J1=16.0 Hz, J2=12.0 Hz, 1H; dd, J1=6.4 Hz, J2=12.0 Hz, 1H; m, 1H; s, 1H; s, 1H; d, J=16.0 Hz, 1H; m, 2H; d, J=7.6 Hz, 2H; t, J=7.6 Hz, 2H; s, 1H

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys Medchem (6) 1 of 6

Substance Effect

Antiviral

80/124

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Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

MDCK

Substance RN

27575416View in Reaxys

Substance Name

2-allyl-3-methoxy-5-[(E)-styryl]phenol

Measurement Parameter

IC50

Unit

μg/ml

Quantitative value

0.09

Measurement pX

6.47

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys 2 of 6

Substance Effect

Antiviral

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

VERO

Substance RN

27575416View in Reaxys

Substance Name

2-allyl-3-methoxy-5-[(E)-styryl]phenol

Measurement Parameter

IC50

Unit

μg/ml

Quantitative value

0.54

Measurement pX

5.69

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys 3 of 6

Substance Effect

Antiviral

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

Huh-7.5

Substance RN

27575416View in Reaxys

Substance Name

2-allyl-3-methoxy-5-[(E)-styryl]phenol

Measurement Parameter

Tested

Qualitative value

Not published

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys 4 of 6

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

MT4

Substance RN

27575416View in Reaxys

Substance Name

2-allyl-3-methoxy-5-[(E)-styryl]phenol

Measurement Parameter

Tested

Qualitative value

Not published

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys 5 of 6

Substance Effect

Neuroprotective

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

PC12

Substance RN

27575416View in Reaxys

81/124

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Substance Name

2-allyl-3-methoxy-5-[(E)-styryl]phenol

Substance Dose

10 μM

Measurement Parameter

% Inhibition

Unit

Quantitative value

86.7

Measurement pX

5.81

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys 6 of 6

Substance Effect

Neuroprotective

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

PC12

Substance RN

27575416View in Reaxys

Substance Name

2-allyl-3-methoxy-5-[(E)-styryl]phenol

Substance Dose

10 μM

Measurement Parameter

% Inhibition

Unit

Quantitative value

87.6

Measurement pX

5.85

Patent; Li, Zhuorong; Ji, Xingyue; Xue, Situ; Zheng, Guanghui; Li, Yuhuan; Tao, Peizhen; Jiang, Jiandong; US2014/371232; (2014); (A1) English, View in Reaxys

Reaxys ID 30676971 View in Reaxys

22/67 Chemical Name: 4-allyl-6-methoxybenzene-1,3-diol Linear Structure Formula: C10H12O3 Molecular Formula: C10H12O3 Molecular Weight: 180.203 InChI Key: RPEPCEMMUUSYSA-UHFFFAOYSA-N Note:

Druglikeness (1) 1 of 1

LogP

1.939

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.69

Lipinski Number

Veber Number

Reaxys ID 2447356 View in Reaxys

23/67

CAS Registry Number: 19772-34-0 Chemical Name: 2-Methoxy-5-allyl-1,4-hydrochinon Linear Structure Formula: C10H12O3 Molecular Formula: C10H12O3

O OH

82/124

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Molecular Weight: 180.203 Type of Substance: isocyclic InChI Key: WFEUDPLRTRDWSB-UHFFFAOYSA-N Note: Druglikeness (1) 1 of 1

LogP

1.939

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.69

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

114 - 116

Solvent (Melting Point)

aq. ethanol

Saiki et al.; Yakugaku Zasshi; vol. 88; (1968); p. 185,189; Chem.Abstr.; vol. 69; nb. 67001; (1968), View in Reaxys

Reaxys ID 2590612 View in Reaxys

24/67 CAS Registry Number: 4647-03-4 Chemical Name: 3-Phenyl-3-(2-hydroxy-3,4-dimethoxy-phenyl)-propen Linear Structure Formula: C17H18O3 Molecular Formula: C17H18O3 Molecular Weight: 270.328 Type of Substance: isocyclic InChI Key: GQGBVXHXSFPCSJ-UHFFFAOYSA-N Note:

OH O

Substance Label (1) Label References IId

Barnes,M.F. et al.; Tetrahedron; vol. 21; (1965); p. 2707 - 2715, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.927

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Boiling Point (1) Boiling Point [°C] 95 - 105

Pressure (Boiling Point) [Torr]

References

0.03

Barnes,M.F. et al.; Tetrahedron; vol. 21; (1965); p. 2707 - 2715, View in Reaxys

Reaxys ID 2591803 View in Reaxys

25/67

83/124

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CAS Registry Number: 21022-91-3 Chemical Name: 2-Methoxy-4-allyl-6-benzyloxy-phenol Linear Structure Formula: C17H18O3 Molecular Formula: C17H18O3 Molecular Weight: 270.328 Type of Substance: isocyclic InChI Key: ILUYFLSQPIXLGW-UHFFFAOYSA-N Note:

O HO

Substance Label (1) Label References Kaneko; Matsui; Agricultural and Biological Chemistry; vol. 32; (1968); p. 995,1000, View in Reaxys

XIIIc Druglikeness (1) 1 of 1

LogP

4.181

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Further Information (1) Description (Fur- References ther Information) Further information

Kaneko; Matsui; Agricultural and Biological Chemistry; vol. 32; (1968); p. 995,1000, View in Reaxys

Reaxys ID 2978251 View in Reaxys

26/67 CAS Registry Number: 4647-02-3 Chemical Name: 3-Phenyl-3-(2'-hydroxy-6'-methoxy-phenyl)propen Linear Structure Formula: C16H16O2 Molecular Formula: C16H16O2 Molecular Weight: 240.302 Type of Substance: isocyclic InChI Key: LXIOEMFHFQBLMZ-UHFFFAOYSA-N Note:

Substance Label (1) Label References IVa

Barnes,M.F. et al.; Tetrahedron; vol. 21; (1965); p. 2707 - 2715, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.28

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Reaxys ID 2985035 View in Reaxys

27/67

84/124

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CAS Registry Number: 6848-23-3 Linear Structure Formula: C16H15DO2 Molecular Formula: C16H16O2 Molecular Weight: 241.294 Type of Substance: isocyclic InChI Key: NTJUVKLOVZNZST-DYCDLGHISA-N Note:

Substance Label (1) Label References Barnes,M.F. et al.; Tetrahedron; vol. 21; (1965); p. 2707 - 2715, View in Reaxys

IIb Druglikeness (1) 1 of 1

LogP

4.28

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Barnes,M.F. et al.; Tetrahedron; vol. 21; (1965); p. 2707 - 2715, View in Reaxys

Reaxys ID 2987100 View in Reaxys

28/67 CAS Registry Number: 6848-28-8 Linear Structure Formula: C16H15DO2 Molecular Formula: C16H16O2 Molecular Weight: 241.294 Type of Substance: isocyclic InChI Key: LXIOEMFHFQBLMZ-DYCDLGHISA-N Note:

O O

Substance Label (1) Label References IVb

Barnes,M.F. et al.; Tetrahedron; vol. 21; (1965); p. 2707 - 2715, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.28

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

85/124

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Barnes,M.F. et al.; Tetrahedron; vol. 21; (1965); p. 2707 - 2715, View in Reaxys

Reaxys ID 3133514 View in Reaxys

29/67 Chemical Name: 2-ethoxy-5-allyl-3-methoxy-phenol; 3-Oxy-5methoxy-4-aethoxy-1-allyl-benzol; 2-Aethoxy-5-allyl-3-methoxyphenol Linear Structure Formula: C12H16O3 Molecular Formula: C12H16O3 Molecular Weight: 208.257 Type of Substance: isocyclic InChI Key: AXTALYGICRYIPC-UHFFFAOYSA-N Note:

HO O O

Druglikeness (1) 1 of 1

LogP

2.894

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Related Structure (1) Referenced Com- References pound 2-ethoxy-4-allyl-6- Beilstein Handbook, View in Reaxys methoxy-phenol

Reaxys ID 3281051 View in Reaxys

30/67 Chemical Name: 2-ethoxy-4-allyl-6-methoxy-phenol; 4-Oxy-3methoxy-5-aethoxy-1-allyl-benzol; 2-Aethoxy-4-allyl-6-methoxyphenol Linear Structure Formula: C12H16O3 Molecular Formula: C12H16O3 Molecular Weight: 208.257 Type of Substance: isocyclic InChI Key: IAUCACTUBNRSCP-UHFFFAOYSA-N Note:

Druglikeness (1) 1 of 1

LogP

2.894

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Boiling Point (1) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

86/124

2017-11-11 21:18:18

153 - 155

Kafuku; Itikawa; Kato; Yakugaku Zasshi; nb. 533; (1926); p. 58; Chem. Zentralbl.; vol. 97; nb. II; (1926); p. 2791, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5287

Kafuku; Itikawa; Kato; Yakugaku Zasshi; nb. 533; (1926); p. 58; Chem. Zentralbl.; vol. 97; nb. II; (1926); p. 2791, View in Reaxys

589

Density (1) 1 of 1

Density [g·cm-3]

1.0818

Reference Temperature [°C]

Measurement Temperature [°C]

Kafuku; Itikawa; Kato; Yakugaku Zasshi; nb. 533; (1926); p. 58; Chem. Zentralbl.; vol. 97; nb. II; (1926); p. 2791, View in Reaxys

Reaxys ID 3312687 View in Reaxys

31/67 CAS Registry Number: 99184-41-5 Chemical Name: 2-allyl-4,5,6-trichloro-3-methoxy-phenol; 2Allyl-4,5,6-trichlor-3-methoxy-phenol Linear Structure Formula: C10H9Cl3O2 Molecular Formula: C10H9Cl3O2 Molecular Weight: 267.539 Type of Substance: isocyclic InChI Key: KNVUBTWIRBYPBS-UHFFFAOYSA-N Note:

O Cl

Cl Cl

Druglikeness (1) 1 of 1

LogP

4.479

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Derivative (1) Comment (Derivative) 2,4-dinitro-benzoyl derivative (mp: 110-111 degree ) Boiling Point (1) Boiling Point [°C] 170 - 172

References Castelfranchi; Perrotti; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1201,1218, View in Reaxys

Pressure (Boiling Point) [Torr]

References

Castelfranchi; Perrotti; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1201,1218, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.6759

Castelfranchi; Perrotti; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1201,1218, View in Reaxys

589

87/124

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Reaxys ID 4504387 View in Reaxys

32/67 CAS Registry Number: 112890-03-6 Linear Structure Formula: C18H20O3 Molecular Formula: C18H20O3 Molecular Weight: 284.355 Type of Substance: isocyclic InChI Key: BCMIRWAUXVDPOK-UHFFFAOYSA-N Note:

Substance Label (1) Label References 6

Reddy, Kalakota S.; Ko, Ok-Hyun; Ho, David; Persons, Paul E.; Cassady, John M.; Tetrahedron Letters; vol. 28; nb. 27; (1987); p. 3075 - 3078, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.559

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Reaxys ID 4754793 View in Reaxys

33/67 CAS Registry Number: 135547-26-1 Linear Structure Formula: C19H20O3 Molecular Formula: C19H20O3 Molecular Weight: 296.366 Type of Substance: isocyclic InChI Key: VMFOXXVQLWQDON-UHFFFAOYSA-N Note:

OH O

Substance Label (1) Label References 3

Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.119

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

88/124

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Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys

Medchem (1) 1 of 1

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

4754793View in Reaxys

Substance Name

Qualitative Results

insecticidal activity on Aedes aegypti (Mosquito larvae); mycotoxic activity on Artemia salina (Brine shrimp); no nematocidal activity on Caenorhabditis elegaus, Panagrellus redivivus (axenic)

Measurement Parameter

Qualitative

Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys

Reaxys ID 4757656 View in Reaxys

34/67 CAS Registry Number: 135547-27-2 Linear Structure Formula: C20H22O3 Molecular Formula: C20H22O3 Molecular Weight: 310.393 Type of Substance: isocyclic InChI Key: GVSUGGMBXFXZBK-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 2

Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.44

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

NMR Spectroscopy (2)

89/124

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1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys

Medchem (1) 1 of 1

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

4757656View in Reaxys

Substance Name

Qualitative Results

anti-bacterial activity on Streptococcus aureus, Staphylococcus epidermidis, Escherichia coli; anti-fungal activity on Candida albicans, Aspergillus flavus, Gleosporum sp., Rhizoctonia sp.

Measurement Parameter

Qualitative

Nitao, James K.; Nair, Muraleedharan G.; Thorogood, Deborah L.; Johnson Kelly S.; Scriber, J. Mark; Phytochemistry (Elsevier); vol. 30; nb. 7; (1991); p. 2193 - 2195, View in Reaxys

Reaxys ID 4802410 View in Reaxys

35/67 CAS Registry Number: 135396-53-1 Chemical Name: 4-Chloro-3-methoxy-2-(2-propenyl)phenol Linear Structure Formula: C10H11ClO2 Molecular Formula: C10H11ClO2 Molecular Weight: 198.649 Type of Substance: isocyclic InChI Key: UXMHGSCYOWZGDA-UHFFFAOYSA-N Note:

O Cl

Substance Label (1) Label References 50

Xu, Simon L.; Xia, Haiji; Moore, Harold W.; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6094 6103, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.235

H Bond Donors

H Bond Acceptors

90/124

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Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Xu, Simon L.; Xia, Haiji; Moore, Harold W.; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6094 - 6103, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Xu, Simon L.; Xia, Haiji; Moore, Harold W.; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6094 - 6103, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Xu, Simon L.; Xia, Haiji; Moore, Harold W.; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6094 - 6103, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3420 - 680 cm**(-1)

Xu, Simon L.; Xia, Haiji; Moore, Harold W.; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6094 - 6103, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) electron impact (EI); spectrum

Xu, Simon L.; Xia, Haiji; Moore, Harold W.; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6094 6103, View in Reaxys

Reaxys ID 4981641 View in Reaxys

36/67 CAS Registry Number: 115546-33-3 Linear Structure Formula: C11H14O2 Molecular Formula: C11H14O2 Molecular Weight: 178.231 Type of Substance: isocyclic InChI Key: BBLFBORHUCDBBP-UHFFFAOYSA-N

O OH

91/124

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Note: Substance Label (1) Label References 26b

Al-Khayat, Isam K. L.; Dean, Francis M.; Varma, Rajender S.; Tetrahedron; vol. 43; nb. 20; (1987); p. 4649 - 4662, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.839

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Al-Khayat, Isam K. L.; Dean, Francis M.; Varma, Rajender S.; Tetrahedron; vol. 43; nb. 20; (1987); p. 4649 4662, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Al-Khayat, Isam K. L.; Dean, Francis M.; Varma, Rajender S.; Tetrahedron; vol. 43; nb. 20; (1987); p. 4649 4662, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3570 - 1120 cm**(-1)

Al-Khayat, Isam K. L.; Dean, Francis M.; Varma, Rajender S.; Tetrahedron; vol. 43; nb. 20; (1987); p. 4649 4662, View in Reaxys

Reaxys ID 4984561 View in Reaxys

37/67 CAS Registry Number: 115546-34-4 Chemical Name: 3-methoxy-2-methyl-4-(prop-2-enyl)phenol Linear Structure Formula: C11H14O2 Molecular Formula: C11H14O2 Molecular Weight: 178.231 Type of Substance: isocyclic InChI Key: JJAATZMCXNGAQL-UHFFFAOYSA-N Note:

Substance Label (1) Label References

92/124

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26c

Al-Khayat, Isam K. L.; Dean, Francis M.; Varma, Rajender S.; Tetrahedron; vol. 43; nb. 20; (1987); p. 4649 - 4662, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.839

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Al-Khayat, Isam K. L.; Dean, Francis M.; Varma, Rajender S.; Tetrahedron; vol. 43; nb. 20; (1987); p. 4649 4662, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Al-Khayat, Isam K. L.; Dean, Francis M.; Varma, Rajender S.; Tetrahedron; vol. 43; nb. 20; (1987); p. 4649 4662, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

3410 - 1284 cm**(-1)

Al-Khayat, Isam K. L.; Dean, Francis M.; Varma, Rajender S.; Tetrahedron; vol. 43; nb. 20; (1987); p. 4649 4662, View in Reaxys

Reaxys ID 5435923 View in Reaxys

38/67 Linear Structure Formula: C15H20O3 Molecular Formula: C15H20O3 Molecular Weight: 248.322 Type of Substance: heterocyclic InChI Key: OSBHVSLCFXUOPZ-UHFFFAOYSA-N Note:

O O

Druglikeness (1) 1 of 1

LogP

3.782

H Bond Donors

H Bond Acceptors

93/124

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Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Reaxys ID 5571780 View in Reaxys

39/67 Linear Structure Formula: C18H20O3 Molecular Formula: C18H20O3 Molecular Weight: 284.355 Type of Substance: isocyclic InChI Key: GZAZHSYYDZTVHM-UHFFFAOYSA-N Note:

O O

Druglikeness (1) 1 of 1

LogP

4.291

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Reaxys ID 5585347 View in Reaxys

40/67

CAS Registry Number: 83864-82-8 Chemical Name: dimethylovobatol Linear Structure Formula: C20H22O3 Molecular Formula: C20H22O3 Molecular Weight: 310.393 Type of Substance: isocyclic InChI Key: VPHNHEBOUYQCAJ-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 1b

Ito; Iida; Ichino; Tsunezuka; Hattori; Namba; Chemical and pharmaceutical bulletin; vol. 30; nb. 9; (1982); p. 3347 - 3353, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.651

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy)

94/124

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Ito; Iida; Ichino; Tsunezuka; Hattori; Namba; Chemical and pharmaceutical bulletin; vol. 30; nb. 9; (1982); p. 3347 - 3353, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Ito; Iida; Ichino; Tsunezuka; Hattori; Namba; Chemical and pharmaceutical bulletin; vol. 30; nb. 9; (1982); p. 3347 - 3353, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1640 - 1500 cm**(-1)

Ito; Iida; Ichino; Tsunezuka; Hattori; Namba; Chemical and pharmaceutical bulletin; vol. 30; nb. 9; (1982); p. 3347 - 3353, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Ito; Iida; Ichino; Tsunezuka; Hattori; Namba; Chemical and pharmaceutical bulletin; vol. 30; nb. 9; (1982); p. 3347 - 3353, View in Reaxys

Medchem (1) 1 of 1

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Substance RN

5585347View in Reaxys

Substance Name

Qualitative Results

Antibacterial activities against Streptococcus mutans MT5091 and OMZ176

Measurement Parameter

Qualitative

Ito; Iida; Ichino; Tsunezuka; Hattori; Namba; Chemical and pharmaceutical bulletin; vol. 30; nb. 9; (1982); p. 3347 - 3353, View in Reaxys

Reaxys ID 5635571 View in Reaxys

41/67 CAS Registry Number: 84130-99-4 Chemical Name: 2-((4-allyl-2-methoxyphenoxy)methyl)-15crown-5; 2-[(4-allyl-2-methoxyphenoxy)methyl]-15-crown-5 Linear Structure Formula: C21H32O7 Molecular Formula: C21H32O7 Molecular Weight: 396.481 Type of Substance: heterocyclic InChI Key: BWHKMKYCLJZHFQ-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References

95/124

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Dishong, Dennis M.; Diamond, Craig J.; Cinoman, Michael I.; Gokel, Geoge W.; Journal of the American Chemical Society; vol. 105; nb. 3; (1983); p. 586 - 593, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.754

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

64.61

Lipinski Number

Veber Number

Association (MCS) (2) 1 of 2

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

methanol; H2O

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

Ratio of solvents: 9:1

Partner (Association (MCS))

KCl

Dishong, Dennis M.; Diamond, Craig J.; Cinoman, Michael I.; Gokel, Geoge W.; Journal of the American Chemical Society; vol. 105; nb. 3; (1983); p. 586 - 593, View in Reaxys 2 of 2

Description (Association Stability constant of the complex with ... (MCS)) Solvent (Association (MCS))

methanol; H2O

Temperature (Association (MCS)) [°C]

Comment (Association (MCS))

Ratio of solvents: 9:1

Partner (Association (MCS))

NaCl

Dishong, Dennis M.; Diamond, Craig J.; Cinoman, Michael I.; Gokel, Geoge W.; Journal of the American Chemical Society; vol. 105; nb. 3; (1983); p. 586 - 593, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CCl4 scopy) Dishong, Dennis M.; Diamond, Craig J.; Cinoman, Michael I.; Gokel, Geoge W.; Journal of the American Chemical Society; vol. 105; nb. 3; (1983); p. 586 - 593, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3060 - 745 cm**(-1)

96/124

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Dishong, Dennis M.; Diamond, Craig J.; Cinoman, Michael I.; Gokel, Geoge W.; Journal of the American Chemical Society; vol. 105; nb. 3; (1983); p. 586 - 593, View in Reaxys

Reaxys ID 6596775 View in Reaxys

42/67 Chemical Name: 2-allyl-5,6-dimethoxy-3-methylphenol Linear Structure Formula: C12H16O3 Molecular Formula: C12H16O3 Molecular Weight: 208.257 Type of Substance: isocyclic InChI Key: CDTYFSKOLYNFHN-UHFFFAOYSA-N Note:

OH O

Substance Label (1) Label References 16c

Merz; Rauschel; Synthesis; nb. 8; (1993); p. 797 - 802, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.697

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Merz; Rauschel; Synthesis; nb. 8; (1993); p. 797 - 802, View in Reaxys

Reaxys ID 6597746 View in Reaxys

43/67 Chemical Name: 4-allyl-2,3-dimethoxy-5-methylphenol Linear Structure Formula: C12H16O3 Molecular Formula: C12H16O3 Molecular Weight: 208.257 Type of Substance: isocyclic InChI Key: DYLGWXSQFXISCM-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 17c

Merz; Rauschel; Synthesis; nb. 8; (1993); p. 797 - 802, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.697

H Bond Donors

H Bond Acceptors

Rotatable Bonds

97/124

2017-11-11 21:18:18

TPSA

38.69

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Merz; Rauschel; Synthesis; nb. 8; (1993); p. 797 - 802, View in Reaxys

Reaxys ID 7584053 View in Reaxys

44/67 CAS Registry Number: 182010-44-2 Chemical Name: 2-fluoro-5-methoxy-3,4-dimethyl-6-(2-propenyl)phenol Linear Structure Formula: C12H15FO2 Molecular Formula: C12H15FO2 Molecular Weight: 210.248 Type of Substance: isocyclic InChI Key: WGYNEWHSUMJOJK-UHFFFAOYSA-N Note:

HO F

Druglikeness (1) 1 of 1

LogP

3.226

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Reaxys ID 7584054 View in Reaxys

45/67 CAS Registry Number: 1027205-05-5 Linear Structure Formula: C12H15ClO2 Molecular Formula: C12H15ClO2 Molecular Weight: 226.703 Type of Substance: isocyclic InChI Key: RCHWYDLRDZAIMP-UHFFFAOYSA-N Note:

HO Cl

Druglikeness (1) 1 of 1

LogP

3.687

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

98/124

2017-11-11 21:18:18

Veber Number

Reaxys ID 8150385 View in Reaxys

46/67 Linear Structure Formula: C18H20O2 Molecular Formula: C18H20O2 Molecular Weight: 268.356 Type of Substance: isocyclic InChI Key: VFKGGBATGVFQAU-UHFFFAOYSA-N Note:

Substance Label (1) Label References Scheme 2

Stefinovic, Marijan; Snieckus, Victor; Journal of Organic Chemistry; vol. 63; nb. 9; (1998); p. 2808 - 2809, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.959

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Reaxys ID 8273008 View in Reaxys

47/67 Linear Structure Formula: C20H18O2 Molecular Formula: C20H18O2 Molecular Weight: 290.362 Type of Substance: isocyclic InChI Key: XLNGFMPGVGEHBX-UHFFFAOYSA-N Note:

Substance Label (1) Label References 45d

Tiedemann, Ralf; Turnbull, Philip; Moore, Harold W.; Journal of Organic Chemistry; vol. 64; nb. 11; (1999); p. 4030 - 4041, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.819

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Reaxys ID 8685040 View in Reaxys

48/67

99/124

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CAS Registry Number: 193895-11-3 Linear Structure Formula: C10H12O3 Molecular Formula: C10H12O3 Molecular Weight: 180.203 Type of Substance: isocyclic InChI Key: NAWRLHVSWBLNMW-UHFFFAOYSA-N Note:

O OH OH

Substance Label (1) Label References 47

Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.368

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.69

Lipinski Number

Veber Number

NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

21.47

Frequency (NMR Spectroscopy) [MHz]

125

Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys 2 of 6

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

21.47

Frequency (NMR Spectroscopy) [MHz]

125

Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys 3 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

100/124

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Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys 4 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

21.47

Frequency (NMR Spectroscopy) [MHz]

400

Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys 5 of 6

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

21.47

Frequency (NMR Spectroscopy) [MHz]

400

Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys 6 of 6

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Pettus, Thomas R.R.; Inoue, Masayuki; Chen, Xiao-Tao; Danishefsky, Samuel J.; Journal of the American Chemical Society; vol. 122; nb. 26; (2000); p. 6160 - 6168, View in Reaxys

Reaxys ID 13767963 View in Reaxys

49/67 Chemical Name: 4-allyl-2-fluoro-5-methoxyphenol Linear Structure Formula: C10H11FO2 Molecular Formula: C10H11FO2 Molecular Weight: 182.195 InChI Key: NPMLRQZJMMZKST-UHFFFAOYSA-N Note:

O OH F

Druglikeness (1)

101/124

2017-11-11 21:18:18

1 of 1

LogP

2.774

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

6.85; 6.52; 5.85 - 6; 5.05; 5; 3.78

Kind of signal

d, J=11.8 Hz, 1H; d, J=7.8 Hz, 1H; m, 1H; m, 3H; m, 1H; s, 3H

H NMR (CDCl3): δ6.85 (d, J=11.8 Hz, 1H), 6.52 (d, J=7.8 Hz, 1H), 6.0-5.85 (m, 1H), 5.05 (m, 3H), 5.00 (m, 1H), 3.78 (s, 3H)

Patent; Aktiebolaget Astra; Cornell Research Foundation, Inc.; The University of Maryland at Baltimore; US5523475; (1996); (A1) English, View in Reaxys Mass Spectrometry (1) Comment (Mass Peak Spectrometry) Molecular peak

References

182 m/z

Patent; Aktiebolaget Astra; Cornell Research Foundation, Inc.; The University of Maryland at Baltimore; US5523475; (1996); (A1) English, View in Reaxys

Reaxys ID 14397961 View in Reaxys

50/67 CAS Registry Number: 852109-76-3 Chemical Name: 1-allyl-2-(benzyloxy)-4-methoxybenzene Linear Structure Formula: C17H18O2 Molecular Formula: C17H18O2 Molecular Weight: 254.329 InChI Key: IRBLDBKYBPBDPC-UHFFFAOYSA-N Note:

Substance Label (1) Label References Intermediate 1

Patent; WYETH A CORPORATION OF THE STATE OF DELAWARE; WO2005/44812; (2005); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.644

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

18.46

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties

102/124

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colorless

Patent; WYETH A CORPORATION OF THE STATE OF DELAWARE; WO2005/44812; (2005); (A1) English, View in Reaxys

Reaxys ID 15827526 View in Reaxys

51/67 CAS Registry Number: 65632-89-5 Chemical Name: 2-allyl-3-methoxy-5-methylphenol Linear Structure Formula: C11H14O2 Molecular Formula: C11H14O2 Molecular Weight: 178.231 InChI Key: CHSKUHCPZBUOHP-UHFFFAOYSA-N Note:

Substance Label (1) Label References 4b

Biswas, Bidyut; Sarkar, Debayan; Venkateswaran, Ramanathapuram V.; Tetrahedron; vol. 64; nb. 14; (2008); p. 3212 - 3216, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.05

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Biswas, Bidyut; Sarkar, Debayan; Venkateswaran, Ramanathapuram V.; Tetrahedron; vol. 64; nb. 14; (2008); p. 3212 - 3216, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Biswas, Bidyut; Sarkar, Debayan; Venkateswaran, Ramanathapuram V.; Tetrahedron; vol. 64; nb. 14; (2008); p. 3212 - 3216, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

103/124

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Biswas, Bidyut; Sarkar, Debayan; Venkateswaran, Ramanathapuram V.; Tetrahedron; vol. 64; nb. 14; (2008); p. 3212 - 3216, View in Reaxys

Reaxys ID 19471790 View in Reaxys

52/67 CAS Registry Number: 1146930-80-4 Chemical Name: 3-(4-allylphenoxy)-5-allyl-2-methoxyphenol Linear Structure Formula: C19H20O3 Molecular Formula: C19H20O3 Molecular Weight: 296.366 InChI Key: RINJCWTVKHEVGT-UHFFFAOYSA-N Note:

Patent-Specific Data (1) References Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/239955; (2009); (A1) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

5.33

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties colorless

Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/239955; (2009); (A1) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

(CDCl3): 7.12 (H-3' and 5', d, J = 8.7 Hz), 6.92 (H-2' and H-6', d, J = 8.1 Hz), 6.56 (H-6, d, J = 2.1 Hz), 6.28 (H-4, d, J = 2.4 Hz), 5.97 (H-8 and H-8', m), 5.09 (H-9 and H-9', m), 3.89 (3H, s), 3.36 (H-7', d, J = 6.6 Hz), 3.23 (H-7, d, J = 6.6 Hz).

Comment (NMR Spectroscopy)

Signals given

1H-NMR

Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/239955; (2009); (A1) English, View in Reaxys

Reaxys ID 19567674 View in Reaxys

53/67

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CAS Registry Number: 1158306-01-4 Chemical Name: tulsinol F; 1-allyl-4-(5-allyl-2-hydroxy-3-methoxyphenoxy)-3-(4-allyl-2-methoxyphenoxy)-5-methoxybenzene Linear Structure Formula: C30H32O6 Molecular Formula: C30H32O6 Molecular Weight: 488.58 InChI Key: FZWAPOLATYIVKF-UHFFFAOYSA-N Note:

O O

O O O

Druglikeness (1) 1 of 1

LogP

7.934

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

66.38

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence) troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

105/124

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1 of 1

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Solvent (IR Spectroscopy)

potassium bromide

Suzuki, Akiko; Shirota, Osamu; Mori, Kanami; Sekita, Setsuko; Fuchino, Hiroyuki; Takano, Akihito; Kuroyanagi, Masanori; Chemical and Pharmaceutical Bulletin; vol. 57; nb. 3; (2009); p. 245 - 251, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation)

mol peak

References Suzuki, Akiko; Shirota, Osamu; Mori, Kanami; Sekita, Setsuko; Fuchino, Hiroyuki; Takano, Akihito; Kuroyanagi, Masanori; Chemical and Pharmaceutical Bulletin; vol. 57; nb. 3; (2009); p. 245 - 251, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 222; 275 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

11300; 2400

Suzuki, Akiko; Shirota, Osamu; Mori, Kanami; Sekita, Setsuko; Fuchino, Hiroyuki; Takano, Akihito; Kuroyanagi, Masanori; Chemical and Pharmaceutical Bulletin; vol. 57; nb. 3; (2009); p. 245 - 251, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product leaves of Ocimum Suzuki, Akiko; Shirota, Osamu; Mori, Kanami; Sekita, Setsuko; Fuchino, Hiroyuki; Takano, Akihito; sanctum L., Tulsi, Kuroyanagi, Masanori; Chemical and Pharmaceutical Bulletin; vol. 57; nb. 3; (2009); p. 245 - 251, purchased at a View in Reaxys market in Kathmandu, Nepal, in August 2003 Medchem (1) 1 of 1

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against Leishmania major promastigotes upon incubation for 72 h at 27 degree c by MTT method

Biological Species/NCBI Leishmania major ID Substance RN

19567674View in Reaxys

Measurement Parameter

IC50

Unit

µg/mL

Qualitative value

Quantitative value

23.8

Measurement pX

4.31

Reaxys ID 19720587 View in Reaxys

54/67

106/124

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CAS Registry Number: 1192659-13-4 Chemical Name: 5-allyl-3-methoxy-4-(3-methylbut-2-enyl)benzene-1,2-diol Linear Structure Formula: C15H20O3 Molecular Formula: C15H20O3 Molecular Weight: 248.322 InChI Key: QBYPBNSRIHOEAF-UHFFFAOYSA-N Note:

O HO

Druglikeness (1) 1 of 1

LogP

4.247

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

49.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

Takaoka, Shigeki; Takaoka, Noriko; Minoshima, Yuka; Huang, Jian-Mei; Kubo, Miwa; Harada, Kenichi; Hioki, Hideaki; Fukuyama, Yoshiyasu; Tetrahedron; vol. 65; nb. 40; (2009); p. 8354 - 8361, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

107/124

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(Electron impact); Spectrum EI (Electron impact); Spectrum

Medchem (1) 1 of 1

Substance Effect

Neurotrophic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

Bioassay Details

Effect : neurite outgrowthSpecies : SD ratBioassay : primary cultured fetal cortical neuronsneurite length = 249 μm in control (0.5 % ethanol)

Biological Species/NCBI Rattus norvegicus ID Substance RN

19720587View in Reaxys

Substance Name

Substance Dose

1 µM

Qualitative Results

neurite length 366 μm

Measurement Parameter

Qualitative

Reaxys ID 23138362 View in Reaxys

55/67 CAS Registry Number: 1415560-47-2 Chemical Name: (S,E)-2-(3-cyclohexyl-1-phenylallyl)-5-methoxyphenol Linear Structure Formula: C22H26O2 Molecular Formula: C22H26O2 Molecular Weight: 322.447 InChI Key: MXDHUDLXLPDICN-PKHIPVCBSA-N Note:

Substance Label (1) Label References 8h

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 19968, View in Reaxys

Druglikeness (1) 1 of 1

LogP

7.139

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Enantiomeric excess [%ee]

108/124

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Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

6.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) spectrum Use (1) Laboratory Use and Handling

References

supporting information

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys

Location

References

Avoid contact with supporting inforair mation

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys

109/124

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Reaxys ID 23138365 View in Reaxys

56/67 CAS Registry Number: 1415560-52-9 Linear Structure Formula: C16H16O2 Molecular Formula: C16H16O2 Molecular Weight: 240.302 InChI Key: NTJUVKLOVZNZST-AWEZNQCLSA-N Note:

Substance Label (1) Label References 9

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 19968, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.28

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

126

Location

supporting information

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

110/124

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Comment (IR Spectroscopy)

film

References

supporting information

Luan, Yi; Schaus, Scott E.; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 19965 - 19968, View in Reaxys

Reaxys ID 23866959 View in Reaxys

O OH

57/67 Linear Structure Formula: C20H22O5 Molecular Formula: C20H22O5 Molecular Weight: 342.392 InChI Key: RNTCLCBMCDZPHW-UHFFFAOYSA-N Note:

O OH

Substance Label (1) Label References 1

Druglikeness (1) 1 of 1

LogP

4.839

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.15

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties colourless

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Description (NMR Spec- COSY (Correlation Spectroscopy) troscopy)

111/124

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Nucleus (NMR Spectroscopy)

1H; 1H

Solvents (NMR Spectro- methanol-d4 scopy) Saleem, Muhammad; Parveen, Shehla; Riaz, Naheed; Ashraf, Muhammad; Ejaz, Syeda Abida; Waris, Hafiz Muhammad; Ali, Muhammad Shaiq; Malik, Abdul; Jabbar, Abdul; Journal of the Chemical Society of Pakistan; vol. 35; nb. 3; (2013); p. 911 - 915, View in Reaxys 3 of 4

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence) troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Saleem, Muhammad; Parveen, Shehla; Riaz, Naheed; Ashraf, Muhammad; Ejaz, Syeda Abida; Waris, Hafiz Muhammad; Ali, Muhammad Shaiq; Malik, Abdul; Jabbar, Abdul; Journal of the Chemical Society of Pakistan; vol. 35; nb. 3; (2013); p. 911 - 915, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution mass spectrometry (HRMS); electron impact (EI); fragmentation pattern; spectrum

UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 206; 272 VIS) [nm] Log epsilon

4.58; 4.46

Saleem, Muhammad; Parveen, Shehla; Riaz, Naheed; Ashraf, Muhammad; Ejaz, Syeda Abida; Waris, Hafiz Muhammad; Ali, Muhammad Shaiq; Malik, Abdul; Jabbar, Abdul; Journal of the Chemical Society of Pakistan; vol. 35; nb. 3; (2013); p. 911 - 915, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product

112/124

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whole plant LauSaleem, Muhammad; Parveen, Shehla; Riaz, Naheed; Ashraf, Muhammad; Ejaz, Syeda Abida; Waris, naea intybacea Hafiz Muhammad; Ali, Muhammad Shaiq; Malik, Abdul; Jabbar, Abdul; Journal of the Chemical Society Jacq.; collected of Pakistan; vol. 35; nb. 3; (2013); p. 911 - 915, View in Reaxys from Cholistan Desert (DistrictBahawalpur, Punjab), Pakistan Medchem (6) 1 of 6

Target Name

acetylcholinesterase

Target Synonyms

ace (acetylcholinesterase); ace-1 (acetylcholinesterase); ace1 (acetylcholinesterase); acetyl.beta-methylcholinesterase; acetylcholine acetylhydrolase; acetylcholine hydrolase; acetylcholinesterase; acetylthiocholinesterase; ache (acetylcholinesterase); ache1; agap001356; cg17907; choline esterase i; true cholinesterase

Target, Subunit, Species acetylcholinesterase Target Mutant/Chimera Details

acetylcholinesterase:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

23866959View in Reaxys

Substance Name

1-Table-2, Compound 1

Substance Dose

0.500000 mM

Measurement Parameter

% Inhibition

Unit

Quantitative value

45.2

Deviation

0.140000

Measurement pX

3.22

Concomitants: Compound RN

3916578; 1896821

Concomitants: Compound name

Acetylthiocholine iodide; DTNB

Concomitants: Compound role

SUB; COM

Target Name

acetylcholinesterase

Target Synonyms

Target, Subunit, Species acetylcholinesterase Target Mutant/Chimera Details

acetylcholinesterase:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

23866959View in Reaxys

Substance Name

1-Table-2, Compound 1

Measurement Parameter

IC50

Unit

µM

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Quantitative value

357.56

Deviation

0.880000

Measurement pX

3.45

Concomitants: Compound RN

3916578; 1896821

Concomitants: Compound name

Acetylthiocholine iodide; DTNB

Concomitants: Compound role

SUB; COM

Target Name

Cholinesterase

Target Synonyms

acylcholine acylhydrolase (cholinesterase); anticholineesterase; bche (cholinesterase); benzoylcholinesterase; btchoease; butyrylcholine esterase; butyrylcholinesterase; che1 (cholinesterase); choline esterase; choline esterase ii; choline esterase ii (unspecific); cholinesterase; eq-bche; non-specific cholinesterase; propionylcholinesterase; pseudocholinesterase

Target, Subunit, Species Cholinesterase Target Mutant/Chimera Details

Cholinesterase:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

23866959View in Reaxys

Substance Name

1-Table-2, Compound 1

Substance Dose

0.500000 mM

Measurement Parameter

% Inhibition

Unit

Quantitative value

53.1

Deviation

0.250000

Measurement pX

3.35

Concomitants: Compound RN

3916578; 1896821

Concomitants: Compound name

Acetylthiocholine iodide; DTNB

Concomitants: Compound role

SUB; COM

Target Name

Cholinesterase

Target Synonyms

Target, Subunit, Species Cholinesterase Target Mutant/Chimera Details

Cholinesterase:Wild

Bioassay Category

In Vitro (Efficacy)

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Bioassay Name

Enzymology inhibition

Substance RN

23866959View in Reaxys

Substance Name

1-Table-2, Compound 1

Measurement Parameter

IC50

Unit

µM

Quantitative value

416.77

Deviation

0.480000

Measurement pX

3.38

Concomitants: Compound RN

3916578; 1896821

Concomitants: Compound name

Acetylthiocholine iodide; DTNB

Concomitants: Compound role

SUB; COM

Target Name

Lipoxygenase

Target Synonyms

lipoxygenase

Target, Subunit, Species Lipoxygenase Target Mutant/Chimera Details

Lipoxygenase:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

23866959View in Reaxys

Substance Name

1-Table-2, Compound 1

Substance Dose

0.500000 mM

Measurement Parameter

% Inhibition

Unit

Quantitative value

91.7

Deviation

0.270000

Measurement pX

4.34

Target Name

Lipoxygenase

Target Synonyms

lipoxygenase

Target, Subunit, Species Lipoxygenase Target Mutant/Chimera Details

Lipoxygenase:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

23866959View in Reaxys

Substance Name

1-Table-2, Compound 1

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Measurement Parameter

IC50

Unit

µM

Quantitative value

56.3

Deviation

0.100000

Measurement pX

4.25

Reaxys ID 28248092 View in Reaxys

58/67 Chemical Name: 3-ethyl-5-methoxy-2-(prop-2-en-1-yl)phenol Linear Structure Formula: C12H16O2 Molecular Formula: C12H16O2 Molecular Weight: 192.258 InChI Key: LQKACUGAFNOUJI-UHFFFAOYSA-N Note:

Substance Label (1) Label References 28

Shao, Wenjie; Clive, Derrick L. J.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3211 - 3216, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.514

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Shao, Wenjie; Clive, Derrick L. J.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3211 - 3216, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

116/124

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Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Shao, Wenjie; Clive, Derrick L. J.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3211 - 3216, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

chloroform-d1

Shao, Wenjie; Clive, Derrick L. J.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3211 - 3216, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution Shao, Wenjie; Clive, Derrick L. J.; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3211 - 3216, mass spectrome- View in Reaxys try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Reaxys ID 28678562 View in Reaxys

59/67 Chemical Name: 5-allyl-1-(4′-allylphenoxy)-3-methoxy-2-(methoxymethoxy)benzene Linear Structure Formula: C21H24O4 Molecular Formula: C21H24O4 Molecular Weight: 340.419 InChI Key: JAUWHYOVNVDJSN-UHFFFAOYSA-N Note:

O O O

Substance Label (1) Label References 13

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.598

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

36.92

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

117/124

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Crystal Property Description (1) Colour & Other References Properties yellow

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522-L, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522-L, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522-L, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) electrospray ionisation (ESI); spectrum

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Pilkington, Lisa I.; Barker, David; Synlett; vol. 26; nb. 17; (2015); p. 2425 - 2428; Art.No: ST-2015-D0522L, View in Reaxys

Reaxys ID 29736366 View in Reaxys

60/67 Chemical Name: 6-allyl-4-iodo-2,3-dimethoxyphenol Linear Structure Formula: C11H13IO3 Molecular Formula: C11H13IO3 Molecular Weight: 320.127 InChI Key: JCCVDLBKEVYUEN-UHFFFAOYSA-N Note:

OH O

O I

Substance Label (1)

118/124

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Label

References

Druglikeness (1) 1 of 1

LogP

3.328

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties brown

supporting information

References Bochicchio, Antonella; Cefola, Rossella; Choppin, Sabine; Colobert, Françoise; Di Noia, Maria Antonietta; Funicello, Maria; Hanquet, Gilles; Pisano, Isabella; Todisco, Simona; Chiummiento, Lucia; Tetrahedron Letters; vol. 57; nb. 36; (2016); p. 4053 4055, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

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Reaxys ID 29848014 View in Reaxys

61/67 Chemical Name: Eugenol Sodium hypochlorite Linear Structure Formula: C10H12O2*ClO(1-)*Na(1+) Molecular Formula: C10H12O2*ClO*Na Molecular Weight: 238.646 InChI Key: NXZNNSSBYYXBID-UHFFFAOYSA-N Note:

O Na + HO

–O

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

52.52

Lipinski Number

Veber Number

Reaxys ID 30229770 View in Reaxys

62/67 Chemical Name: hydrate Eugenol Linear Structure Formula: C10H12O2*H2O Molecular Formula: C10H12O2*H2O Molecular Weight: 182.219 InChI Key: MGAJBSLSRBCWHV-UHFFFAOYSA-N Note:

HO H 2O

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

29.46

Lipinski Number

Veber Number

Reaxys ID 30837018 View in Reaxys

63/67 Chemical Name: 2-allyl-3-bromo-5,6-dimethoxyphenol; 2-Allyl-3-bromo-5,6-dimethoxyphenol Linear Structure Formula: C11H13BrO3 Molecular Formula: C11H13BrO3 Molecular Weight: 273.126 InChI Key: XPBKNQHEMVSFQH-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 26

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.058

H Bond Donors

H Bond Acceptors

Rotatable Bonds

120/124

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TPSA

38.69

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

64 - 69

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties yellow

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) electrospray ionisation (ESI); spectrum

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys

high resolution mass spectrometry (HRMS); electrospray ionisa-

Dittrich, Nora; Pilkington, Lisa I.; Leung, Euphemia; Barker, David; Tetrahedron; vol. 73; nb. 14; (2017); p. 1881 - 1894, View in Reaxys

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tion (ESI); spectrum

Reaxys ID 31038384 View in Reaxys

64/67 Linear Structure Formula: C18H20O3 Molecular Formula: C18H20O3 Molecular Weight: 284.355 InChI Key: HKFHRPASLBMVMO-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References C

Patent; L'OREAL; DALKO, Maria; HITCE, Julien; (48 pag.); WO2016/92074; (2016); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.502

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

27.69

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties yellow

References

Page/Page column 29

Patent; L'OREAL; DALKO, Maria; HITCE, Julien; (48 pag.); WO2016/92074; (2016); (A1) English, View in Reaxys

Reaxys ID 31549189 View in Reaxys

65/67 Chemical Name: 2,6-Dimethoxyphenol 4-Allyl-2,6-dimethoxyphenol Acetosyringone Linear Structure Formula: C8H10O3*C10H12O4*C11H14O3 Molecular Formula: C8H10O3*C10H12O4*C11H14O3 Molecular Weight: 544.599 InChI Key: NLTKGUYPBOLORN-UHFFFAOYSA-N Note:

O O

HO O

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

133.14

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Lipinski Number

Veber Number

Reaxys ID 31647602 View in Reaxys

66/67 Linear Structure Formula: C13H18O4 Molecular Formula: C13H18O4 Molecular Weight: 238.284 InChI Key: CUXCXTOZQCIUPK-VIFPVBQESA-N Note:

OH OH O

Substance Label (1) Label References M12

Yang, Xiao-Nan; Lv, Qian-Qian; Zhao, Qi; Li, Xin-Mei; Yan, Dong-Mei; Yang, Xiu-Wei; Li, Fei; RSC Advances; vol. 7; nb. 64; (2017); p. 40131 - 40140, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.222

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

58.92

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic References data UPLC (Ultra performance liquid chromatography)

Yang, Xiao-Nan; Lv, Qian-Qian; Zhao, Qi; Li, Xin-Mei; Yan, Dong-Mei; Yang, Xiu-Wei; Li, Fei; RSC Advances; vol. 7; nb. 64; (2017); p. 40131 - 40140, View in Reaxys

Mass Spectrometry (1) Description (Mass References Spectrometry) liquid chromatog- Yang, Xiao-Nan; Lv, Qian-Qian; Zhao, Qi; Li, Xin-Mei; Yan, Dong-Mei; Yang, Xiu-Wei; Li, Fei; RSC Adraphy mass spec- vances; vol. 7; nb. 64; (2017); p. 40131 - 40140, View in Reaxys trometry (LCMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Reaxys ID 31839375 View in Reaxys

67/67

OH H 13 3 C

H 13C

Linear Structure Formula: (13)C11H14O3 Molecular Formula: C11H14O3 Molecular Weight: 205.109 InChI Key: FWMPKHMKIJDEMJ-ODZTYCMJSA-N Note:

CH 3

13CH

H 13C 13CH

CH 2

Druglikeness (1) 1 of 1

LogP

2.471

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H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

38.69

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass References Spectrometry) gas chromatogra- Van Erven, Gijs; De Visser, Ries; Merkx, Donny W. H.; Strolenberg, Willem; De Gijsel, Peter; Gruppen, phy mass specHarry; Kabel, Mirjam A.; Analytical Chemistry; vol. 89; nb. 20; (2017); p. 10907 - 10916, View in Reaxys trometry (GCMS); electron impact (EI); spectrum

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