3,4-Dihydroxy-5-methoxybenzaldehyde (5-Hydroxyvanillin) [C8H8O4]

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2 substances in Reaxys

2018-04-22 11h:20m:34s (UTC)

OH HO

1. Query

O O

Search as: As drawn

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Reaxys ID 1956546 View in Reaxys

1/2 CAS Registry Number: 3934-87-0 Chemical Name: 5-hydroxyvanillin; 4,5-dihydroxy-3-methoxybenzaldehyde; 3,4-dihydroxy-5-methoxybenzaldehyde; 3-methoxy-4,5dihydroxybenzaldehyde; 3,4-dihydroxy-5-methoxybenzadehyde; 3,4hydroxy-5-methoxybenzaldehyde; 3,4-dihydroxy-5-methoxy-benzaldehyde Linear Structure Formula: C8H8O4 Molecular Formula: C8H8O4 Molecular Weight: 168.149 Type of Substance: isocyclic InChI Key: RRKMWVISRMWBAL-UHFFFAOYSA-N Note:

OH HO O O

Substance Label (17) Label References 12a

Varró, Gábor; Mattyasovszky, Lenke; Grün, Alajos; Simon, András; Hegedüs, László; Kádas, István; Synthesis (Germany); vol. 50; nb. 3; (2018); p. 625 - 643; Art.No: SS-2017-T0559-OP, View in Reaxys

4

Vanucci-Bacque, Corinne; Chaabouni, Slim; Fabing, Isabelle; Bedos-Belval, Florence; Baltas, Michel; Tetrahedron Letters; vol. 55; nb. 2; (2014); p. 528 - 530, View in Reaxys; Rahmanpour, Rahman; King, Lloyd D.W.; Bugg, Timothy D.H.; Biochemical and Biophysical Research Communications; vol. 482; nb. 1; (2017); p. 57 - 61, View in Reaxys; Vergara, Sebastian; Carda, Miguel; Agut, Raül; Yepes, Lina M.; Vélez, Iván D.; Robledo, Sara M.; Galeano, Wilson Cardona; Medicinal Chemistry Research; vol. 26; nb. 12; (2017); p. 3262 - 3273, View in Reaxys

2

Zhang, Jieyu; Cheah, Yong Shung; Santhanakrishnan, Sridhar; Neoh, Koon Gee; Chai, Christina L.L.; Polymer (United Kingdom); vol. 116; (2017); p. 5 - 15, View in Reaxys

10

Varró, Gábor; Hegedus, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G.; Kádas, István; Journal of Natural Products; vol. 80; nb. 6; (2017); p. 1909 - 1917, View in Reaxys

pre-53

Abraham, Rebecca J.; Stevens, Andrew J.; Young, Kelly A.; Russell, Cecilia; Qvist, Anastasia; Khazandi, Manouchehr; Wong, Hui San; Abraham, Sam; Ogunniyi, Abiodun D.; Page, Stephen W.; O'Handley, Ryan; McCluskey, Adam; Trott, Darren J.; Journal of Medicinal Chemistry; vol. 59; nb. 5; (2016); p. 2126 - 2138, View in Reaxys

VAN005

Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys

9

Varró, Gábor; Hegedűs, László; Simon, András; Kádas, István; Tetrahedron Letters; vol. 57; nb. 14; (2016); p. 1544 - 1546, View in Reaxys

8

Jiang, Yu Lin; Chung, Suhman; Krosky, Daniel J.; Stivers, James T.; Bioorganic and Medicinal Chemistry; vol. 14; nb. 16; (2006); p. 5666 - 5672, View in Reaxys; Gao, Wenqing; Li, Qingyong; Chen, Jian; Wang, Zhichao; Hua, Changlong; Molecules; vol. 18; nb. 12; (2013); p. 15613 - 15623, View in Reaxys

6

Zouhiri, Fatima; Mouscadet, Jean-Francois; Mekouar, Khalid; Desmaele, Didier; Savoure, Delphine; Leh, Herve; Subra, Frederic; Le Bret, Marc; Auclair, Christian; D'Angelo, Jean; Journal of Medicinal Chemistry; vol. 43; nb. 8; (2000); p. 1533 - 1540, View in Reaxys; Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882, View in Reaxys

29bj

Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; CHINTAREDDY, Venkat, R.; WO2013/33093; (2013); (A1) English, View in Reaxys

7

Tsyganov, Dmitry V.; Konyushkin, Leonid D.; Karmanova, Irina B.; Firgang, Sergei I.; Strelenko, Yuri A.; Semenova, Marina N.; Kiselyov, Alex S.; Semenov, Victor V.; Journal of Natural Products; vol. 76; nb. 8; (2013); p. 1485 1491, View in Reaxys

Chart S1/48

Wang, Shenliang; Chang, Young-Tae; Journal of the American Chemical Society; vol. 128; nb. 32; (2006); p. 10380 10381, View in Reaxys

58

Li, Qian; Lee, Jun-Seok; Ha, Chanki; Chan, Beum Park; Yang, Guang; Wen, Biao Gan; Chang, Young-Tae; Angewandte Chemie - International Edition; vol. 43; nb. 46; (2004); p. 6331 - 6335, View in Reaxys

11

Kota, Parvathi; Guo, Dianjing; Zubieta, Chloe; Noel, Joe; Dixon, Richard A.; Phytochemistry; vol. 65; nb. 7; (2004); p. 837 - 846, View in Reaxys

14n

Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio; Organic and biomolecular chemistry; vol. 1; nb. 14; (2003); p. 2474 - 2485, View in Reaxys

12

Guz, Nathan R.; Stermitz, Frank R.; Journal of Natural Products; vol. 63; nb. 8; (2000); p. 1140 - 1145, View in Reaxys

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X

Hyotylainen; Chemosphere; vol. 28; nb. 9; (1994); p. 1641 - 1656, View in Reaxys

Patent-Specific Data (2) Location in Patent References Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys Claim

Patent; International Telephone and Telegraph Corporation; US4465864; (1984); (A) English, View in Reaxys; Patent; Rhone-Poulenc Chimie; US5003091; (1991); (A) English, View in Reaxys; Patent; Domtar Limited; US4065504; (1977); (A) English, View in Reaxys; Patent; L'Oreal S.A.; US6451067; (2002); (B1) English, View in Reaxys; Patent; L'Oreal, S.A.; US6635090; (2003); (B1) English, View in Reaxys; Patent; RHONE-POULENC CHIMIE; EP277894; (1992); (B1) French, View in Reaxys; Patent; Rhone-Poulenc Industries; US4435601; (1984); (A) English, View in Reaxys; Patent; Rhone-Poulenc Chimie; US4933498; (1990); (A) English, View in Reaxys; Patent; L'Oreal S.A.; US6458168; (2002); (B1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.982

H Bond Donors

2

H Bond Acceptors

1

Rotatable Bonds

2

TPSA

66.76

Lipinski Number

4

Veber Number

2

Derivative (3) Comment (Derivative)

References

By formation of compound with CH3COX. Additional data: mass spectrum

Hyotylainen; Chemosphere; vol. 28; nb. 9; (1994); p. 1641 - 1656, View in Reaxys

Na-Salz: UV-Max.: 364 nm, 252 nm, 219 nm (A. + NaOH)

Santavy et al.; Acta Universitatis Palackianae Olomucensis, Facultatis Medicae, Supplementum; vol. 13; (1973); p. 23; Chem.Abstr.; vol. 81; nb. 25219, View in Reaxys

the 2.4-dinitro-phe- Bradley; Robinson; Schwarzenbach; Journal of the Chemical Society; (1930); p. 796,811, View in Reaxys nylhydrazone is decomposing by/at 230 degree Melting Point (19) 1 of 19

Melting Point [°C]

131 - 133

Zhang, Jieyu; Cheah, Yong Shung; Santhanakrishnan, Sridhar; Neoh, Koon Gee; Chai, Christina L.L.; Polymer (United Kingdom); vol. 116; (2017); p. 5 - 15, View in Reaxys 2 of 19

Melting Point [°C]

124 - 126

Solvent (Melting Point)

toluene

Varró, Gábor; Hegedus, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G.; Kádas, István; Journal of Natural Products; vol. 80; nb. 6; (2017); p. 1909 - 1917, View in Reaxys 3 of 19

Melting Point [°C]

129 - 131

Solvent (Melting Point)

toluene

Tsyganov, Dmitry V.; Konyushkin, Leonid D.; Karmanova, Irina B.; Firgang, Sergei I.; Strelenko, Yuri A.; Semenova, Marina N.; Kiselyov, Alex S.; Semenov, Victor V.; Journal of Natural Products; vol. 76; nb. 8; (2013); p. 1485 - 1491, View in Reaxys 4 of 19

Melting Point [°C]

132

Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882, View in Reaxys

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5 of 19

Melting Point [°C]

132 - 134

Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 371 378, View in Reaxys 6 of 19

Melting Point [°C]

131 - 133

Solvent (Melting Point)

toluene

Pettit, George R.; Thornhill, Andrew; Melody, Noeleen; Knight, John C.; Journal of Natural Products; vol. 72; nb. 3; (2009); p. 380 - 388, View in Reaxys 7 of 19

Melting Point [°C]

122

Solvent (Melting Point)

benzene

Lam; Iiyama; Stone; Phytochemistry; vol. 41; nb. 6; (1996); p. 1507 - 1510, View in Reaxys 8 of 19

Melting Point [°C]

131 - 132

Asakawa et al.; Phytochemistry (Elsevier); vol. 15; (1976); p. 1057, View in Reaxys 9 of 19

Melting Point [°C]

130

Santavy et al.; Acta Universitatis Palackianae Olomucensis, Facultatis Medicae, Supplementum; vol. 13; (1973); p. 23; Chem.Abstr.; vol. 81; nb. 25219, View in Reaxys 10 of 19

Melting Point [°C]

133 - 134

Solvent (Melting Point)

benzene

Banerjee et al.; Canadian Journal of Chemistry; vol. 40; (1962); p. 2175, View in Reaxys 11 of 19

Melting Point [°C]

131 - 133.5

Lange; Journal of Organic Chemistry; vol. 27; (1962); p. 2037, View in Reaxys 12 of 19

Melting Point [°C]

130 - 131

Solvent (Melting Point)

benzene

Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2>133; (1932); p. 120,123,124, View in Reaxys 13 of 19

Melting Point [°C]

130 - 131

Solvent (Melting Point)

toluene

Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2>133; (1932); p. 120,123,124, View in Reaxys 14 of 19

Melting Point [°C]

132 - 134

Solvent (Melting Point)

benzene

Bradley; Robinson; Schwarzenbach; Journal of the Chemical Society; (1930); p. 796,811, View in Reaxys 15 of 19

Melting Point [°C]

132 - 134

Solvent (Melting Point)

diethyl ether; light petroleum

Bradley; Robinson; Schwarzenbach; Journal of the Chemical Society; (1930); p. 796,811, View in Reaxys 16 of 19

Melting Point [°C]

131 - 132

Solvent (Melting Point)

benzene

Shriner; McCutchan; Journal of the American Chemical Society; vol. 51; (1929); p. 2194, View in Reaxys 17 of 19

Melting Point [°C]

131 - 132

Solvent (Melting Point)

diethyl ether; light petroleum

Shriner; McCutchan; Journal of the American Chemical Society; vol. 51; (1929); p. 2194, View in Reaxys 18 of 19

Melting Point [°C]

132 - 133

Solvent (Melting Point)

benzene

Spaeth; Roeder; Monatshefte fuer Chemie; vol. 43; (1922); p. 107, View in Reaxys 19 of 19

Melting Point [°C]

132 - 133

Solvent (Melting Point)

diethyl ether; light petroleum

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Spaeth; Roeder; Monatshefte fuer Chemie; vol. 43; (1922); p. 107, View in Reaxys Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882, View in Reaxys; Varró, Gábor; Hegedus, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G.; Kádas, István; Journal of Natural Products; vol. 80; nb. 6; (2017); p. 1909 - 1917, View in Reaxys

Crystal Property Description (4) Colour & Other Location Properties brown

white

References Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882, View in Reaxys; Zhang, Jieyu; Cheah, Yong Shung; Santhanakrishnan, Sridhar; Neoh, Koon Gee; Chai, Christina L.L.; Polymer (United Kingdom); vol. 116; (2017); p. 5 - 15, View in Reaxys; Varró, Gábor; Hegedus, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G.; Kádas, István; Journal of Natural Products; vol. 80; nb. 6; (2017); p. 1909 - 1917, View in Reaxys

Page/Page column 41

Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys

colourless

Pettit, George R.; Thornhill, Andrew; Melody, Noeleen; Knight, John C.; Journal of Natural Products; vol. 72; nb. 3; (2009); p. 380 - 388, View in Reaxys; Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.-Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 371 - 378, View in Reaxys

brown

Kuo, Ping-Chung; Chen, Yi-Hsien; Leu, Yann-Lii; Huang, Chieh-Hung; Liao, Yu-Ren; Lee, E.-Jian; Yang, Mei-Lin; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 4; (2012); p. 557 - 561, 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 NMR Spectroscopy (30) 1 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Zhang, Jieyu; Cheah, Yong Shung; Santhanakrishnan, Sridhar; Neoh, Koon Gee; Chai, Christina L.L.; Polymer (United Kingdom); vol. 116; (2017); p. 5 - 15, View in Reaxys 2 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 101 scopy) [MHz]

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Zhang, Jieyu; Cheah, Yong Shung; Santhanakrishnan, Sridhar; Neoh, Koon Gee; Chai, Christina L.L.; Polymer (United Kingdom); vol. 116; (2017); p. 5 - 15, View in Reaxys 3 of 30

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 300 scopy) [MHz] Location

supporting information

Varró, Gábor; Hegedus, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G.; Kádas, István; Journal of Natural Products; vol. 80; nb. 6; (2017); p. 1909 - 1917, View in Reaxys 4 of 30

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz] Location

supporting information

Varró, Gábor; Hegedus, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G.; Kádas, István; Journal of Natural Products; vol. 80; nb. 6; (2017); p. 1909 - 1917, View in Reaxys 5 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Original Text (NMR Spec- H-NMR (DMSO-D6). δ 3.83 (3H, s, OCH3), 7.06 (1 H, d, Jmeta = 1.8 Hz, Ar-H), 7.03 (1 H, d, Jmeta = troscopy) 1.75 Hz, Ar-H), 9.79 (1 H, s, H-aldehyde) Location

Page/Page column 41

Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys 6 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Original Text (NMR Spec- δ 56.39 (OCH3), 105.40 (Ar-C), 111.29 (Ar-C), 127.76 (Ar-C), 141.50 (Ar-C), 146.33 (Ar-C), troscopy) 148.90 (Ar-C), 191.76 (C-aldehyde). Location

Page/Page column 41

Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys 7 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

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Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 500.1 scopy) [MHz] Tsyganov, Dmitry V.; Konyushkin, Leonid D.; Karmanova, Irina B.; Firgang, Sergei I.; Strelenko, Yuri A.; Semenova, Marina N.; Kiselyov, Alex S.; Semenov, Victor V.; Journal of Natural Products; vol. 76; nb. 8; (2013); p. 1485 - 1491, View in Reaxys 8 of 30

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

18

Frequency (NMR Spectro- 400 scopy) [MHz] Location

supporting information

Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882, View in Reaxys 9 of 30

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

18

Frequency (NMR Spectro- 100 scopy) [MHz] Location

supporting information

Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882, View in Reaxys 10 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 300 scopy) [MHz] Pettit, George R.; Thornhill, Andrew; Melody, Noeleen; Knight, John C.; Journal of Natural Products; vol. 72; nb. 3; (2009); p. 380 - 388, View in Reaxys; Kuo, Ping-Chung; Chen, Yi-Hsien; Leu, Yann-Lii; Huang, Chieh-Hung; Liao, Yu-Ren; Lee, E.-Jian; Yang, Mei-Lin; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 4; (2012); p. 557 - 561, View in Reaxys 11 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 300 scopy) [MHz]

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Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 371 378, View in Reaxys 12 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 75 scopy) [MHz] Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 371 378, View in Reaxys 13 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 75 scopy) [MHz] Kuo, Ping-Chung; Chen, Yi-Hsien; Leu, Yann-Lii; Huang, Chieh-Hung; Liao, Yu-Ren; Lee, E.-Jian; Yang, Mei-Lin; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 4; (2012); p. 557 - 561, View in Reaxys 14 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 250 scopy) [MHz] Location

supporting information

Altemoeller, Martina; Gehring, Timo; Cudaj, Judith; Podlech, Joachim; Goesmann, Helmut; Feldmann, Claus; Rothenberger, Alexander; European Journal of Organic Chemistry; nb. 13; (2009); p. 2130 - 2140, View in Reaxys 15 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 100 scopy) [MHz] Pettit, George R.; Thornhill, Andrew; Melody, Noeleen; Knight, John C.; Journal of Natural Products; vol. 72; nb. 3; (2009); p. 380 - 388, View in Reaxys 16 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 200 scopy) [MHz]

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Zouhiri, Fatima; Mouscadet, Jean-Francois; Mekouar, Khalid; Desmaele, Didier; Savoure, Delphine; Leh, Herve; Subra, Frederic; Le Bret, Marc; Auclair, Christian; D'Angelo, Jean; Journal of Medicinal Chemistry; vol. 43; nb. 8; (2000); p. 1533 - 1540, View in Reaxys 17 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Ellis, James E.; Lenger, Steven R.; Synthetic Communications; vol. 28; nb. 9; (1998); p. 1517 - 1524, View in Reaxys 18 of 30

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Comment (NMR Spectroscopy)

1H-1H

Ellis, James E.; Lenger, Steven R.; Synthetic Communications; vol. 28; nb. 9; (1998); p. 1517 - 1524, View in Reaxys 19 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

tetradeuteriomethanol

Lam; Iiyama; Stone; Phytochemistry; vol. 41; nb. 6; (1996); p. 1507 - 1510, View in Reaxys 20 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

17O

Solvents (NMR Spectroscopy)

acetonitrile

Kolehmainen, Erkki T.; Laihia, Katri P.; Hyoetylaeinen, Juha M. I.; Kauppinen, Reijo T.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 3; (1995); p. 419 - 428, View in Reaxys 21 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

acetone-d6

Temperature (NMR Spectroscopy) [°C]

30

Kolehmainen, Erkki T.; Laihia, Katri P.; Hyoetylaeinen, Juha M. I.; Kauppinen, Reijo T.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 3; (1995); p. 419 - 428, View in Reaxys 22 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

acetone-d6

Temperature (NMR Spectroscopy) [°C]

30

Kolehmainen, Erkki T.; Laihia, Katri P.; Hyoetylaeinen, Juha M. I.; Kauppinen, Reijo T.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 3; (1995); p. 419 - 428, View in Reaxys

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23 of 30

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

acetone-d6

Temperature (NMR Spectroscopy) [°C]

30

Comment (NMR Spectroscopy)

1H-13C.

Kolehmainen, Erkki T.; Laihia, Katri P.; Hyoetylaeinen, Juha M. I.; Kauppinen, Reijo T.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 3; (1995); p. 419 - 428, View in Reaxys 24 of 30

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

acetone-d6

Temperature (NMR Spectroscopy) [°C]

30

Comment (NMR Spectroscopy)

1H-1H.

Kolehmainen, Erkki T.; Laihia, Katri P.; Hyoetylaeinen, Juha M. I.; Kauppinen, Reijo T.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 3; (1995); p. 419 - 428, View in Reaxys 25 of 30

Description (NMR Spectroscopy)

Linewidth of NMR absorption

Kolehmainen, Erkki T.; Laihia, Katri P.; Hyoetylaeinen, Juha M. I.; Kauppinen, Reijo T.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 3; (1995); p. 419 - 428, View in Reaxys 26 of 30

Description (NMR Spectroscopy)

2D-NMR

Kolehmainen, Erkki T.; Laihia, Katri P.; Hyoetylaeinen, Juha M. I.; Kauppinen, Reijo T.; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 3; (1995); p. 419 - 428, View in Reaxys 27 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

dimethylsulfoxide

Schneiders; Stevenson; Journal of Organic Chemistry; vol. 46; nb. 14; (1981); p. 2969 - 2971, View in Reaxys 28 of 30

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectroscopy)

CDCl3; acetone-d6

Schneiders; Stevenson; Journal of Organic Chemistry; vol. 46; nb. 14; (1981); p. 2969 - 2971, View in Reaxys 29 of 30

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

CDCl3; acetone-d6

Comment (NMR Spectroscopy)

1H-1H.

Schneiders; Stevenson; Journal of Organic Chemistry; vol. 46; nb. 14; (1981); p. 2969 - 2971, View in Reaxys 30 of 30

Description (NMR Spectroscopy)

NMR

Asakawa et al.; Phytochemistry (Elsevier); vol. 15; (1976); p. 1057, View in Reaxys

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IR Spectroscopy (4) 1 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (IR Spectroscopy)

film

Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

neat (no solvent, solid phase)

Pettit, George R.; Thornhill, Andrew; Melody, Noeleen; Knight, John C.; Journal of Natural Products; vol. 72; nb. 3; (2009); p. 380 - 388, View in Reaxys; Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.-Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 371 - 378, View in Reaxys; Kuo, Ping-Chung; Chen, Yi-Hsien; Leu, Yann-Lii; Huang, Chieh-Hung; Liao, Yu-Ren; Lee, E.-Jian; Yang, Mei-Lin; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 4; (2012); p. 557 - 561, View in Reaxys 3 of 4

Description (IR Spectroscopy)

IR

Varsanyi et al.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 93; (1977); p. 315,318, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Bands

Santavy et al.; Acta Universitatis Palackianae Olomucensis, Facultatis Medicae, Supplementum; vol. 13; (1973); p. 87; Chem.Abstr.; vol. 81; nb. 25219, View in Reaxys Mass Spectrometry (7) Description (Mass References Spectrometry) electrospray ionisa- Rahmanpour, Rahman; King, Lloyd D.W.; Bugg, Timothy D.H.; Biochemical and Biophysical Research Communition (ESI); speccations; vol. 482; nb. 1; (2017); p. 57 - 61, View in Reaxys; Zhang, Jieyu; Cheah, Yong Shung; Santhanakrishnan, trum Sridhar; Neoh, Koon Gee; Chai, Christina L.L.; Polymer (United Kingdom); vol. 116; (2017); p. 5 - 15, View in Reaxys electron impact (EI); spectrum

Tsyganov, Dmitry V.; Konyushkin, Leonid D.; Karmanova, Irina B.; Firgang, Sergei I.; Strelenko, Yuri A.; Semenova, Marina N.; Kiselyov, Alex S.; Semenov, Victor V.; Journal of Natural Products; vol. 76; nb. 8; (2013); p. 1485 1491, View in Reaxys; Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882, View in Reaxys

EI (Electron impact); Spectrum

Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.-Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 371 - 378, View in Reaxys

HRMS (High reso- Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; lution mass specLee, E.-Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung; European Journal of Medicinal Chemistry; vol. 48; trometry); EI (Elec- (2012); p. 371 - 378, View in Reaxys tron impact); Spectrum ESI (Electrospray ionisation); HRMS (High resolution mass spectrometry); Spectrum

Kuo, Ping-Chung; Chen, Yi-Hsien; Leu, Yann-Lii; Huang, Chieh-Hung; Liao, Yu-Ren; Lee, E.-Jian; Yang, MeiLin; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 4; (2012); p. 557 - 561, View in Reaxys

ESI (Electrospray ionisation); Spectrum

Kuo, Ping-Chung; Chen, Yi-Hsien; Leu, Yann-Lii; Huang, Chieh-Hung; Liao, Yu-Ren; Lee, E.-Jian; Yang, MeiLin; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 4; (2012); p. 557 - 561, View in Reaxys

spectrum; electron impact (EI)

Hyotylainen; Chemosphere; vol. 28; nb. 9; (1994); p. 1641 - 1656, View in Reaxys

UV/VIS Spectroscopy (2)

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1 of 2

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ VIS) [nm]

256; 232; 208

Kuo, Ping-Chung; Chen, Yi-Hsien; Leu, Yann-Lii; Huang, Chieh-Hung; Liao, Yu-Ren; Lee, E.-Jian; Yang, Mei-Lin; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 4; (2012); p. 557 - 561, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Santavy,F. et al.; Collection of Czechoslovak Chemical Communications; vol. 37; (1972); p. 1825 - 1850, View in Reaxys; Santavy et al.; Acta Universitatis Palackianae Olomucensis, Facultatis Medicae, Supplementum; vol. 13; (1973); p. 23; Chem.Abstr.; vol. 81; nb. 25219, View in Reaxys Medchem (7) 1 of 7

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Minimum inhibitory concentration against Staphylococcus aureus in presence of sub-inhibitory amount (30 ug/ml) of berberine

Biological Species/NCBI ID

Staphylococcus aureus

Substance RN

1956546View in Reaxys

Measurement Parameter

MIC

Unit

µg/mL

Qualitative value

=

Quantitative value

3.9

Measurement pX

4.63

Concomitants: Compound name

Berberine (30 ug/mL)

Concomitants: Compound role

COM

Patent; COLORADO STATE UNIVERSITY RESEARCH FOUNDATION; TUFTS UNIVERSITY; WO2001/7034; (2001); (A1), View in Reaxys 2 of 7

Target Name

Multidrug resistance protein 1

Target Synonyms

abcb1; atp-binding cassette sub-family b member 1; ben; benomyl resistance protein 1; bmr; bmr1; mdr1; mdr1b; multidrug resistance protein 1; multidrug-efflux transporter 1; p-glycoprotein; p-glycoprotein 1; pgp1; pgy1

Target, Subunit, Species

Multidrug resistance protein 1

Target Mutant/Chimera Details

Multidrug resistance protein 1:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory activity against P-glycoprotein mediated compound efflux was determined

Substance RN

1956546View in Reaxys

Measurement Parameter

Qualitative

Qualitative value

Not Published

Patent; COLORADO STATE UNIVERSITY RESEARCH FOUNDATION; TUFTS UNIVERSITY; WO2001/7034; (2001); (A1), View in Reaxys 3 of 7

Target Name

Uracil-DNA glycosylase [human]

Target Synonyms

dgu; udg; ung; ung1; ung15; uracil-dna glycosylase

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Target Uniprot ID

p13051

Target PDB ID

1akz; 1dpu; 1emh; 1emj; 1q3f; 1ssp; 1ugh; 1yuo; 2hxm; 2oxm; 2oyt; 2ssp; 3fcf; 3fci; 3fck; 3fcl; 3tkb; 4skn; 5ayr; 5jk7

Target, Subunit, Species

Uracil-DNA glycosylase [human]

Target Mutant/Chimera Details

Uracil-DNA glycosylase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

Pharmacokinetic

Bioassay Details

In vitro inhibitory concentration against human Uracil-DNA Glycosylase 2 (33.3 pM) upon incubation for 30 min at ambient temperature and pH 8.0 (10 mM Tris-HCl) with the compound dissolved in DMSO determined by HTS assay; No inhibition

Biological Species/NCBI ID

human

Substance RN

1956546View in Reaxys

Measurement Parameter

Concentration

Unit

mM

Qualitative value

=

Quantitative value

1

Jiang, Yu Lin; Chung, Suhman; Krosky, Daniel J.; Stivers, James T.; Bioorganic and Medicinal Chemistry; vol. 14; nb. 16; (2006); p. 5666 - 5672, View in Reaxys 4 of 7

Target Name

Neuraminidase [Influenza A virus (H1N1)]

Target Synonyms

neuraminidase

Target, Subunit, Species

Neuraminidase [Influenza A virus (H1N1)]

Target Mutant/Chimera Details

Neuraminidase [Influenza A virus (H1N1)]:Wild

Target Species (Bioactivity)

Influenza A virus (H1N1)

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

1956546View in Reaxys

Substance Dose

125 μg/ml

Measurement Parameter

% Inhibition

Unit

%

Quantitative value

81

Measurement pX

3.76

Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys 5 of 7

Substance Effect

Cytotoxic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

MDCK cell line

Substance RN

1956546View in Reaxys

Measurement Parameter

CC50

Unit

μM

Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Quantitative value

150

Measurement pX

3.82

Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys 6 of 7

Target Name

Neuraminidase [Influenza A virus (H1N1)]

Target Synonyms

neuraminidase

Target, Subunit, Species

Neuraminidase [Influenza A virus (H1N1)]

Target Mutant/Chimera Details

Neuraminidase [Influenza A virus (H1N1)]:Wild

Target Species (Bioactivity)

Influenza A virus (H1N1)

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Substance RN

1956546View in Reaxys

Measurement Parameter

IC50

Unit

μM

Quantitative value

68

Measurement pX

4.17

Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys 7 of 7

Substance Effect

Antiviral

Bioassay Category

In Vitro (Efficacy)

Cells/Cell Lines

MDCK cell line

Substance RN

1956546View in Reaxys

Measurement Parameter

IC50

Unit

μM

Measurement Object

Plaque formation

Quantitative value

42.2398

Measurement pX

4.37

Patent; UNIVERSITI SAINS MALAYSIA; MALAYSIAN INSTITUTE OF PHARMACEUTICALS AND NUTRACEUTICALS; WAHAB, Habibah A.; HARIONO, Maywan; KAMARULZAMAN, Ezatul Ezleen; (68 pag.); WO2016/24857; (2016); (A2) English, View in Reaxys

Reaxys ID 9481973 View in Reaxys

HO

2/2 CAS Registry Number: 934634-10-3 Chemical Name: [3-OC(2)H3]-5-hydroxyvanillin Linear Structure Formula: C8H5 (2)H3O4 Molecular Formula: C8H8O4 Molecular Weight: 171.125 Type of Substance: isocyclic InChI Key: RRKMWVISRMWBAL-FIBGUPNXSA-N Note:

OH

O 2

H 2

2H

H

O

Substance Label (2) Label References

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33b

Sakakibara, Norikazu; Nakatsubo, Tomoyuki; Suzuki, Shiro; Shibata, Daisuke; Shimada, Mikio; Umezawa, Toshiaki; Organic and Biomolecular Chemistry; vol. 5; nb. 5; (2007); p. 802 - 815, View in Reaxys

14o

Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio; Organic and biomolecular chemistry; vol. 1; nb. 14; (2003); p. 2474 - 2485, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.982

H Bond Donors

2

H Bond Acceptors

1

Rotatable Bonds

2

TPSA

66.76

Lipinski Number

4

Veber Number

2

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