1,3-Benzodioxole-5-carboxylic acid (Piperonylic acid) [C8H6O4] by Asch

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2018-06-02 11h:33m:32s (UTC)

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Search as: As drawn ) AND (RX.PXRN=150206))

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2018-06-02 11:34:14

Reaxys ID 150206 View in Reaxys

1/1 CAS Registry Number: 94-53-1 Chemical Name: Piperonylic acid Linear Structure Formula: CH2O2C6H3COOH Molecular Formula: C8H6O4 Molecular Weight: 166.133 Type of Substance: heterocyclic InChI Key: VDVJGIYXDVPQLP-UHFFFAOYSA-N Note:

O HO

Substance Label (69) Label References 1

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Erbing, Elis; Sanz-Marco, Amparo; Vázquez-Romero, Ana; Malmberg, Jesper; Johansson, Magnus J.; GómezBengoa, Enrique; Martín-Matute, Belén; ACS Catalysis; vol. 8; nb. 2; (2018); p. 920 - 925, View in Reaxys

Yu, Han; Ru, Shi; Zhai, Yongyan; Dai, Guoyong; Han, Sheng; Wei, Yongge; ChemCatChem; vol. 10; nb. 6; (2018); p. 1253 - 1257, View in Reaxys

Jiang, Xingguo; Ma, Shengming; Synthesis (Germany); vol. 50; nb. 8; (2018); p. 1629 - 1639, View in Reaxys

Degorce, Sebastien; Delouvrie, Benedicte; Davey, Paul R.J.; Didelot, Myriam; Germain, Herve; Harris, Craig S.; Brempt, Christine Lambert-Van Der; Lebraud, Honorine; Ouvry, Gilles; Tetrahedron Letters; vol. 53; nb. 45; (2012); p. 6078 - 6082, View in Reaxys; Barbosa, Maria Leticia De Castro; Lima, Lidia Moreira; Tesch, Roberta; Sant'Anna, Carlos Mauricio R.; Totzke, Frank; Kubbutat, Michael H.G.; Schaechtele, Christoph; Laufer, Stefan A.; Barreiro, Eliezer J.; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 1 - 14, View in Reaxys; Huang, Xiaobo; Zhang, Bingchuan; Xu, Hui; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 18; (2017); p. 4336 4340, View in Reaxys

Fu, Zhengyan; He, Jiangpeng; Tong, Aiping; Xie, Yongmei; Wei, Yuquan; Synthesis (Germany); vol. 45; nb. 20; (2013); p. 2843 - 2852; Art.No: SS-2013-H0366-OP, View in Reaxys; Ovian, John M.; Kelly, Christopher B.; Pistritto, Vincent A.; Leadbeater, Nicholas E.; Organic Letters; vol. 19; nb. 6; (2017); p. 1286 - 1289, View in Reaxys

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Ponnala, Shashikanth; Kapadia, Nirav; Harding, Wayne Wesley; MedChemComm; vol. 6; nb. 4; (2015); p. 601 605, View in Reaxys; Schwendenwein, Daniel; Fiume, Giuseppe; Weber, Hansjörg; Rudroff, Florian; Winkler, Margit; Advanced Synthesis and Catalysis; vol. 358; nb. 21; (2016); p. 3414 - 3421, View in Reaxys; Shimomaki, Katsuya; Murata, Kei; Martin, Ruben; Iwasawa, Nobuharu; Journal of the American Chemical Society; vol. 139; nb. 28; (2017); p. 9467 - 9470, View in Reaxys

HPip

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Song, Lijuan; Xiao, Jing; Dong, Wanrong; Peng, Zhihong; An, Delie; European Journal of Organic Chemistry; vol. 2017; nb. 2; (2017); p. 341 - 349, View in Reaxys

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Y2n

Liang, Qianmao; Chen, Yongfei; Yu, Kailin; Chen, Cheng; Zhang, Shouxiang; Wang, Aoli; Wang, Wei; Wu, Hong; Liu, Xiaochuan; Wang, Beilei; Wang, Li; Hu, Zhenquan; Wang, Wenchao; Ren, Tao; Zhang, Shanchun; Liu, Qingsong; Yun, Cai-Hong; Liu, Jing; European Journal of Medicinal Chemistry; vol. 131; (2017); p. 107 - 125, View in Reaxys

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13c

Yuan, Zigao; Sun, Qinsheng; Li, Dan; Miao, Shuangshuang; Chen, Shaopeng; Song, Lu; Gao, Chunmei; Chen, Yuzong; Tan, Chunyan; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 281 - 292, View in Reaxys

2{8}

Li, Yong; Meng, Jiang-Ping; Lei, Jie; Chen, Zhong-Zhu; Tang, Dian-Yong; Zhu, Jin; Zhang, Jin; Xu, Zhi-Gang; ACS Combinatorial Science; vol. 19; nb. 5; (2017); p. 324 - 330, View in Reaxys

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Ahmed, Maaz S.; Mannel, David S.; Root, Thatcher W.; Stahl, Shannon S.; Organic Process Research and Development; vol. 21; nb. 9; (2017); p. 1388 - 1393, View in Reaxys

Chen, Zhen-Bang; Liu, Kui; Zhang, Fang-Ling; Yuan, Qing; Zhu, Yong-Ming; Organic and Biomolecular Chemistry; vol. 15; nb. 38; (2017); p. 8078 - 8083, View in Reaxys

Giacomini, Daria; Musumeci, Rosario; Galletti, Paola; Martelli, Giulia; Assennato, Lorenzo; Sacchetti, Gianni; Guerrini, Alessandra; Calaresu, Enrico; Martinelli, Marianna; Cocuzza, Clementina; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 604 - 614, View in Reaxys

Jiang, Fen; Guo, An-ping; Xu, Jia-cheng; Wang, Hui-Jie; Mo, Xiao-fei; You, Qi-Dong; Xu, Xiao-Li; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 1 - 14, View in Reaxys

Ahn, Sungwan; Han, Young Taek; Tetrahedron Letters; vol. 58; nb. 51; (2017); p. 4779 - 4780, View in Reaxys

Patent; YONSEI University Office of Research Affairs / University Industry Foundation; Park Tae-seon; (22 pag.); KR101787318; (2017); (B1) Korean, View in Reaxys

0401-113

Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.); CN107383024; (2017); (A) Chinese, View in Reaxys

Zheng, Rui; Zhou, Qizhong; Gu, Haining; Jiang, Huajiang; Wu, Jiashou; Jin, Zhengneng; Han, Deman; Dai, Guoliang; Chen, Rener; Tetrahedron Letters; vol. 55; nb. 41; (2014); p. 5671 - 5675, View in Reaxys; Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 - 4610, View in Reaxys

Daydé-Cazals, Bénédicte; Fauvel, Bénédicte; Singer, Mathilde; Feneyrolles, Clémence; Bestgen, Benoit; Gassiot, Fanny; Spenlinhauer, Aurélia; Warnault, Pierre; Van Hijfte, Nathalie; Borjini, Nozha; Chevé, Gwénaël; Yasri, Abdelaziz; Journal of Medicinal Chemistry; vol. 59; nb. 8; (2016); p. 3886 - 3905, View in Reaxys

meta-1

Zhang, Jing; Shrestha, Ruja; Hartwig, John F.; Zhao, Pinjing; Nature Chemistry; vol. 8; nb. 12; (2016); p. 1144 1151, View in Reaxys

Osako, Takao; Torii, Kaoru; Uozumi, Yasuhiro; RSC Advances; vol. 5; nb. 4; (2015); p. 2647 - 2654, View in Reaxys

Hmba

Wen, Xianhong; Zhang, Huan; Xu, Kai; Sun, Jiahui; Ye, Jiaying; Jin, Shouwen; Wang, Daqi; Journal of Molecular Structure; vol. 1094; (2015); p. 46 - 60, View in Reaxys

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15W%4&

Fernandes, Ítalo A.; De Almeida, Letícia; Ferreira, Patrícia Espuri; Marques, Marcos J.; Rocha, Raíssa P.; Coelho, Luiz F.L.; Carvalho, Diogo T.; Viegas, Claudio; Bioorganic and Medicinal Chemistry Letters; vol. 25; nb. 16; (2015); p. 3346 - 3349; Art.No: 22758, View in Reaxys

Jacobson, Clare E.; Martinez-Muñoz, Noelia; Gorin, David J.; Journal of Organic Chemistry; vol. 80; nb. 14; (2015); p. 7305 - 7310, View in Reaxys

HL1

Jin, Shouwen; Zhang, Huan; Xu, Kai; Ye, Xianghang; Zhang, Yani; Fang, Yang; Wang, Daqi; Polyhedron; vol. 95; (2015); p. 108 - 119, View in Reaxys

13a

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HL3

Jin, Shouwen; Luo, Yiting; Wang, Daqi; Shi, Jiazhong; Li, Siwei; Shen, Shaohua; Xu, Yijie; Zeitschrift fur Anorganische und Allgemeine Chemie; vol. 640; nb. 8-9; (2014); p. 1717 - 1726, View in Reaxys

Wang, Yong; Kang, Qiang; Organic Letters; vol. 16; nb. 16; (2014); p. 4190 - 4193, View in Reaxys

Chang, Meng-Yang; Tsai, Chung-Yu; Tetrahedron Letters; vol. 55; nb. 40; (2014); p. 5548 - 5550, View in Reaxys

Lo Monte, Fabio; Kramer, Thomas; Gu, Jiamin; Brodrecht, Martin; Pilakowski, Johannes; Fuertes, Ana; Dominguez, Juan Manuel; Plotkin, Batya; Eldar-Finkelman, Hagit; Schmidt, Boris; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 26 - 40, View in Reaxys

HL2

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Liu, Hongqiang; Shi, Guangfa; Pan, Shulei; Jiang, Yuyu; Zhang, Yanghui; Organic Letters; vol. 15; nb. 16; (2013); p. 4098 - 4101, View in Reaxys

Gerard, Baudouin; O'Shea, Morgan Welzel; Donckele, Etienne; Kesavan, Sarathy; Akella, Lakshmi B.; Xu, Hao; Jacobsen, Eric N.; Marcaurelle, Lisa A.; ACS Combinatorial Science; vol. 14; nb. 11; (2012); p. 621 - 630, View in Reaxys

Patent; Intitut Català d'Investigació Química (ICIQ); EP2311788; (2011); (A1) English, View in Reaxys

Ke, Shaoyong; Li, Zhong; Qian, Xuhong; Bioorganic and Medicinal Chemistry; vol. 16; nb. 16; (2008); p. 7565 7572, View in Reaxys

substrate to 11f

Legeay, Jean Christophe; Vanden Eynde, Jean Jacques; Bazureau, Jean Pierre; Tetrahedron Letters; vol. 48; nb. 6; (2007); p. 1063 - 1068, View in Reaxys

Product, Tab.1, run 7

Lim, Minkyung; Yoon, Cheol Min; An, Gwangil; Rhee, Hakjune; Tetrahedron Letters; vol. 48; nb. 22; (2007); p. 3835 - 3839, View in Reaxys

Li, Huanrong; Guan, Bingtao; Wang, Wenjin; Xing, Dong; Fang, Zhao; Wan, Xiaobing; Yang, Liping; Shi, Zhangjie; Tetrahedron; vol. 63; nb. 35; (2007); p. 8430 - 8434, View in Reaxys

Broggini, Gianluigi; Colombo, Francesco; De Marchi, Ivan; Galli, Simona; Martinelli, Michela; Zecchi, Gaetano; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1495 - 1501, View in Reaxys

Chen, Yu-Chang; Liao, Chang-Hui; Chen, Ih-Sheng; Phytochemistry; vol. 68; nb. 15; (2007); p. 2101 - 2111, View in Reaxys

B25

Sunnerheim, Kerstin; Nordqvist, Anneli; Nordlander, Goeran; Borg-Karlson, Anna-Karin; Unelius, C. Rickard; Bohman, Bjoern; Nordenhem, Henrik; Hellqvist, Claes; Karlen, Anders; Journal of Agricultural and Food Chemistry; vol. 55; nb. 23; (2007); p. 9365 - 9372, View in Reaxys

acid, tab 1/c,d

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Alvarez, Heiddy Marquez; Barbosa, Dayse P.; Fricks, Alini Tinoco; Aranda, Donato A. G.; Valdes, Ricardo H.; Antunes; Organic Process Research and Development; vol. 10; nb. 5; (2006); p. 941 - 943, View in Reaxys

255a

Patent; METHYLGENE, INC.; WO2005/30704; (2005); (A1) English, View in Reaxys

run no. 31

Khurana, Jitender M.; Chauhan, Sushma; Bansal, Geeti; Monatshefte fur Chemie; vol. 135; nb. 1; (2004); p. 83 - 87, View in Reaxys

27 Ar=C6H3-3,4OCH2O

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B10

Johansson, Per-Ola; Chen, Yantao; Belfrage, Anna Karin; Blackman, Michael J.; Kvarnstroem, Ingemar; Jansson, Katarina; Vrang, Lotta; Hamelink, Elizabeth; Hallberg, Anders; Rosenquist, Asa; Samuelsson, Bertil; Journal of Medicinal Chemistry; vol. 47; nb. 13; (2004); p. 3353 - 3366, View in Reaxys

Hatim, Jaywant Govind; Joshi, Vidya; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 43; nb. 12; (2004); p. 2689 - 2695, View in Reaxys

Nery, Marcelo S.; Ribeiro, Renata P.; Lopes, Claudio C.; Lopes, Rosangela S. C.; Synthesis; nb. 2; (2003); p. 272 276, View in Reaxys

R''CO2H (P)

Dahlgren, Anders; Kvarnstroem, Ingemar; Vrang, Lotta; Hamelink, Elizabeth; Hallberg, Anders; Rosenquist, Asa; Samuelsson, Bertil; Bioorganic and Medicinal Chemistry; vol. 11; nb. 6; (2003); p. 827 - 841, View in Reaxys

Zhang, Fagen; Fan, Peter W.; Liu, Xuemei; Shen, Lixin; Van Breemen, Richard B.; Bolton, Judy L.; Chemical Research in Toxicology; vol. 13; nb. 1; (2000); p. 53 - 62, View in Reaxys; Sengupta, Saumitra; Mondal, Somnath; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 41; nb. 4; (2002); p. 854 - 855, View in Reaxys

3,4-OCH2O-PhCOOH, 14e

Garcia, Javier; Nicolas, Ernesto; Albericio, Fernando; Michelotti, Enrique L.; Tice, Colin M.; Tetrahedron Letters; vol. 43; nb. 42; (2002); p. 7495 - 7498, View in Reaxys

acid of 30

Tempest, Paul; Ma, Vu; Thomas, Samuel; Hua, Zheng; Kelly, Michael G.; Hulme, Christopher; Tetrahedron Letters; vol. 42; nb. 30; (2001); p. 4959 - 4962, View in Reaxys

2 (R=3,4-OCH2OPh)

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10, Table 5, entry 28

Nagayama; Shimizu; Yamamoto; Bulletin of the Chemical Society of Japan; vol. 74; nb. 10; (2001); p. 1803 - 1815, View in Reaxys

Harayama, Takashi; Akamatsu, Hisashi; Okamura, Kana; Miyagoe, Taeko; Akiyama, Toshihiko; Abe, Hitoshi; Takeuchi, Yasuo; Journal of the Chemical Society. Perkin Transactions 1; nb. 5; (2001); p. 523 - 528, View in Reaxys

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R3CO2H to 17

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ac.for acylazide,eq.16

Rigby, James H.; Laurent, Stephane; Dong, Weitong; Danca; Tetrahedron; vol. 56; nb. 52; (2000); p. 10101 - 10111, View in Reaxys

acid in Table 1., run Rigby, James H.; Danca, M. Diana; Tetrahedron Letters; vol. 40; nb. 38; (1999); p. 6891 - 6894, View in Reaxys 2 R3COOH to comp. 8-13,17

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CXXII

Rudenko; Pragst; Russian Journal of Organic Chemistry; vol. 34; nb. 11; (1998); p. 1589 - 1626, View in Reaxys

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys

Patent-Specific Data (9) Prophetic ComLocation in Patent pound

References Patent; NOVARTIS AG; BEHNKE, Dirk; BETSCHART, Claudia; COTESTA, Simona; GERSPACHER, Marc; HINTERMANN, Samuel; ROY, Bernard Lucien; VON MATT, Anette; WAGNER, Juergen; WO2010/86366; (2010); (A1) English, View in Reaxys Patent; ADDEX PHARMA SA; WO2008/117175; (2008); (A2) English, View in Reaxys Patent; PROSIDION LIMITED; WO2005/85245; (2005); (A1) English, View in Reaxys

prophetic product

Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; EP839801; (1998); (A2) English, View in Reaxys; Patent; Jacquot, Roland; Grieneisen, Jean-Louis; US2004/158068; (2004); (A1) English, View in Reaxys Patent; YAMANOUCHI PHARMACEUTICAL CO. LTD.; EP1186601; (2002); (A1) English, View in Reaxys Patent; American Home Products; US6344451; (2002); (B1) English, View in Reaxys Patent; Sankyo Company, Limited; EP1167366; (2002); (A1) English, View in Reaxys Patent; WARNER-LAMBERT COMPANY; EP1193261; (2002); (A1) English, View in Reaxys Claim

Patent; Rhodia Chimie; US6180830; (2001); (B2) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.126

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

55.76

Lipinski Number

Veber Number

Derivative (5) Comment (Derivative)

References

4-bromo-phenacyl ester (mp: 165.5)

Berger; Acta Chemica Scandinavica (1947-1973); vol. 10; (1956); p. 638,640, View in Reaxys

anilide (mp: 146-147 degree )

Gertler; Haller; Journal of the American Chemical Society; vol. 64; (1942); p. 1741, View in Reaxys

<1>naphthylamide (mp: 192.5-193 degree )

Gertler; Haller; Journal of the American Chemical Society; vol. 64; (1942); p. 1741, View in Reaxys

<2>naphthylamide (mp: 156.5-157.5 degree )

Gertler; Haller; Journal of the American Chemical Society; vol. 64; (1942); p. 1741, View in Reaxys

Natrium-Salz : UV- Santavy et al.; Acta Univ. Palack. Olomuc. Suppl. XIII; p. 46 - 50, View in Reaxys Abs.maxima in Ae-

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thanol + NaOH : 291 und 253 nm Melting Point (45) 1 of 45

Melting Point [°C]

231.4 - 233

Solvent (Melting Point)

Petroleum ether; ethyl acetate

Jiang, Xingguo; Ma, Shengming; Synthesis (Germany); vol. 50; nb. 8; (2018); p. 1629 - 1639, View in Reaxys 2 of 45

Melting Point [°C]

226 - 228

Location

supporting information

Huang, Xiaobo; Zhang, Bingchuan; Xu, Hui; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 18; (2017); p. 4336 4340, View in Reaxys 3 of 45

Melting Point [°C]

228 - 229

Location

supporting information

Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 - 4610, View in Reaxys 4 of 45

Melting Point [°C]

229 - 231

Location

supporting information

Melting Point [°C]

236 - 238

Location

supporting information

Zhang, Xiao; Zhang, Wen-Zhen; Shi, Ling-Long; Guo, Chun-Xiao; Zhang, Ling-Ling; Lu, Xiao-Bing; Chemical Communications; vol. 48; nb. 50; (2012); p. 6292 - 6294, View in Reaxys 6 of 45

Melting Point [°C]

226.6 - 229.1

Location

supporting information

Sedelmeier, Joerg; Ley, Steven V.; Baxendale, Ian R.; Baumann, Marcus; Organic Letters; vol. 12; nb. 16; (2010); p. 3618 3621, View in Reaxys 7 of 45

Melting Point [°C]

225 - 227

Dam, Johan Hygum; Madsen, Robert; European Journal of Organic Chemistry; nb. 27; (2009); p. 4666 - 4673, View in Reaxys 8 of 45

Melting Point [°C]

233 - 234

Location

supporting information

Correa, Arkaitz; Martin, Ruben; Journal of the American Chemical Society; vol. 131; nb. 44; (2009); p. 15974 - 15975, View in Reaxys 9 of 45

Melting Point [°C]

228.42

Matos, M. Agostinha R.; Monte, Manuel J.S.; Sousa, Clara C.S.; Almeida, Ana R.R.P.; Morais, Victor M.F.; Organic and Biomolecular Chemistry; vol. 2; nb. 6; (2004); p. 908 - 914, View in Reaxys 10 of 45

Melting Point [°C]

229 - 230

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys; Scholz; Monatshefte fuer Chemie; vol. 110; (1979); p. 1471, View in Reaxys; Jaeger, David A.; Ward, Mary Darlene; Dutta, Aloke K.; Journal of Organic Chemistry; vol. 53; nb. 7; (1988); p. 1577 - 1580, View in Reaxys 11 of 45

Melting Point [°C]

227 - 229

Solvent (Melting Point)

acetone; petroleum ether

Rao, E. Venkata; Murthy, M. Sree Rama; Ward, Robert S.; Phytochemistry (Elsevier); vol. 23; nb. 7; (1984); p. 1493 - 1502, View in Reaxys 12 of 45

Melting Point [°C]

225 - 227

Solvent (Melting Point)

benzene

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Anjaneyulu et al.; Tetrahedron; vol. 33; (1977); p. 133,135,139,140,143, View in Reaxys; Anjaneyulu, A. S. R.; Ramaiah, P. Atchuta; Row, L. Ramachandra; Venkateswarlu, R.; Pelter, A.; Ward, R. S.; Tetrahedron; vol. 37; nb. 21; (1981); p. 3641 3652, View in Reaxys 13 of 45

Melting Point [°C]

222 - 225

Kobayashi, Shigeru; Imakura, Yasuhiro; Horikawa, Ritsuko; Chemical & Pharmaceutical Bulletin; vol. 28; nb. 4; (1980); p. 1287 - 1293, View in Reaxys 14 of 45

Nakano,T. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 2107 - 2112, View in Reaxys

15 of 45

Melting Point [°C]

227

Nakano,T. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 2107 - 2112, View in Reaxys 16 of 45

Melting Point [°C]

214 - 217

McEvoy,F.J.; Albright,J.D.; Journal of Organic Chemistry; vol. 44; (1979); p. 4597 - 4603, View in Reaxys 17 of 45

Melting Point [°C]

212

Garg et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 16; (1978); p. 658, View in Reaxys 18 of 45

Melting Point [°C]

229

Delle Monache et al.; Gazzetta Chimica Italiana; vol. 107; (1977); p. 403,405,406, View in Reaxys 19 of 45

Melting Point [°C]

237 - 239

Pelter et al.; Tetrahedron; vol. 32; (1976); p. 2783,2788, View in Reaxys 20 of 45

Melting Point [°C]

222

Lurik et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 45; (1975); p. 2287,2246, View in Reaxys; Lurik et al.; Pharmaceutical Chemistry Journal; vol. 5; nb. 8; (1971); p. 462; Khimiko-Farmatsevticheskii Zhurnal; vol. 5; nb. 8; (1971); p. 15, View in Reaxys 21 of 45

Melting Point [°C]

208 - 216

Abe; Yahara; Kubo; et al.; Chemical and Pharmaceutical Bulletin; vol. 22; nb. 11; (1974); p. 2650 - 2655, View in Reaxys 22 of 45

Melting Point [°C]

228.5

Baranova et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 47; (1974); p. 2751,2840,2841, View in Reaxys 23 of 45

Melting Point [°C]

229 - 231

Filho et al.; Phytochemistry (Elsevier); vol. 12; (1973); p. 417,419, View in Reaxys 24 of 45

Melting Point [°C]

230

Naik Satam; Bringi; Indian Journal of Chemistry; vol. 11; (1973); p. 209, View in Reaxys 25 of 45

Melting Point [°C]

239 - 240

Govindachari et al.; Indian Journal of Chemistry; vol. 10; (1972); p. 1120, View in Reaxys 26 of 45

Melting Point [°C]

227 - 228

Bowden et al.; Australian Journal of Chemistry; vol. 25; (1972); p. 2659,2668, View in Reaxys 27 of 45

Melting Point [°C]

226

Ramaiah; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 71,74, View in Reaxys 28 of 45

Melting Point [°C]

225

Narasimha Rao; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 231,236, View in Reaxys 29 of 45

Melting Point [°C]

229

Solvent (Melting Point)

methanol

Orphanos,D.G.; Taurin,A.; Canadian Journal of Chemistry; vol. 44; (1966); p. 1875 - 1879, View in Reaxys 30 of 45

Melting Point [°C]

227 - 228

Solvent (Melting Point)

ethanol

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Barton,D.H.R.; Jones,D.W.; Journal of the Chemical Society; (1965); p. 3563 - 3570, View in Reaxys 31 of 45

Melting Point [°C]

228 - 230

Lee,H.H.; Tan,C.H.; Journal of the Chemical Society; (1965); p. 2743 - 2749, View in Reaxys 32 of 45

Melting Point [°C]

225 - 226

Solvent (Melting Point)

ethanol

Chikamoto; Agricultural and Biological Chemistry; vol. 28; (1964); p. 633,634, View in Reaxys 33 of 45

Melting Point [°C]

229

Solvent (Melting Point)

ethanol

Feugeas; Bulletin de la Societe Chimique de France; (1964); p. 1892, View in Reaxys 34 of 45

Melting Point [°C]

219 - 220

Khanna; Seshadri; Tetrahedron; vol. 19; (1963); p. 219,223, View in Reaxys 35 of 45

Melting Point [°C]

226 - 228

Solvent (Melting Point)

benzene

Rangaswami; Sastry; Proceedings - Indian Academy of Sciences, Section A; vol. 57; (1963); p. 135,137, View in Reaxys 36 of 45

Melting Point [°C]

229 - 230

Solvent (Melting Point)

ethanol

Pettit et al.; Journal of Medicinal and Pharmaceutical Chemistry; vol. 5; (1962); p. 800,804, View in Reaxys 37 of 45

Melting Point [°C]

228 - 229

Beroza; Jones; Analytical Chemistry; vol. 34; (1962); p. 1029, View in Reaxys 38 of 45

Melting Point [°C]

228

Ciamician; Silber; Gazzetta Chimica Italiana; vol. 20; (1890); p. 571; Chemische Berichte; vol. 23; (1890); p. 1160, View in Reaxys; Kuraoka; Nippon Kagaku Zasshi; vol. 82; (1961); p. 50, View in Reaxys 39 of 45

Melting Point [°C]

227.5

Solvent (Melting Point)

ethanol; benzene

Dallacker et al.; Monatshefte fuer Chemie; vol. 91; (1960); p. 1089,1096, View in Reaxys 40 of 45

Melting Point [°C]

233 - 235

Solvent (Melting Point)

ethanol

Resplandy; Mentzer; Annales Pharmaceutiques Francaises; vol. 18; (1960); p. 528,539, View in Reaxys 41 of 45

Melting Point [°C]

226 - 227

Solvent (Melting Point)

ethanol

Gensler; Stouffer; Journal of Organic Chemistry; vol. 23; (1958); p. 908, View in Reaxys 42 of 45

Melting Point [°C]

230 - 232

Solvent (Melting Point)

aq. ethanol

Gulland; Macrae; Journal of the Chemical Society; (1932); p. 2231,2235, View in Reaxys 43 of 45

Melting Point [°C]

234 - 235

Solvent (Melting Point)

ethanol

Parijs; Recueil des Travaux Chimiques des Pays-Bas; vol. 49; (1930); p. 33,41, View in Reaxys 44 of 45

Melting Point [°C]

229

Comment (Melting Point)

Sublimiert bei sehr langsamem Erhitzen bei etwa 210grad.

Jobst; Hesse; Justus Liebigs Annalen der Chemie; vol. 199; (1879); p. 73, View in Reaxys 45 of 45

Melting Point [°C]

227.5 - 228.5

Fittig; Mielck; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 52,54; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 140,152, View in Reaxys

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Association (MCS) (1) 1 of 1

Description (Association (MCS))

Stability constant of the complex with ...

Partner (Association (MCS))

3,3-Dibutyl-11-(2-methyl-3,5-dinitro-benzoylamino)-2,4,7-trioxo-2,3,4,7-tetrahydro-1H-12-oxa-1aza-benzo[a]anthracene-9-carboxylic acid methyl ester

Crego, Mercedes; Raposo, Cesar; Caballero, Ma Cruz; Garcia, Estrella; Saez, Javier G.; Moran, Joaquin R.; Tetrahedron Letters; vol. 33; nb. 48; (1992); p. 7437 - 7440, View in Reaxys Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Coleman, Tom; Chao, Rebecca R.; Bruning, John B.; De Voss, James J.; Bell, Stephen G.; RSC Advances; vol. 5; nb. 64; (2015); p. 52007 - 52018, View in Reaxys

Crystal Property Description (5) Colour & Other Location Properties yellow white

References Jiang, Xingguo; Ma, Shengming; Synthesis (Germany); vol. 50; nb. 8; (2018); p. 1629 - 1639, View in Reaxys

supporting informa- Zheng, Rui; Zhou, Qizhong; Gu, Haining; Jiang, Huajiang; Wu, Jiashou; Jin, Zhengneng; tion Han, Deman; Dai, Guoliang; Chen, Rener; Tetrahedron Letters; vol. 55; nb. 41; (2014); p. 5671 - 5675, View in Reaxys; Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 - 4610, View in Reaxys; Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Shashikanth, Sheena; Advanced Synthesis and Catalysis; vol. 359; nb. 3; (2017); p. 419 - 425, View in Reaxys; Ovian, John M.; Kelly, Christopher B.; Pistritto, Vincent A.; Leadbeater, Nicholas E.; Organic Letters; vol. 19; nb. 6; (2017); p. 1286 - 1289, View in Reaxys; Huang, Xiaobo; Zhang, Bingchuan; Xu, Hui; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 18; (2017); p. 4336 - 4340, View in Reaxys; Yang, Zhanhui; Luo, Renshi; Zhu, Zhongpeng; Yang, Xuerong; Tang, Weiping; Organometallics; vol. 36; nb. 21; (2017); p. 4095 - 4098, View in Reaxys

white

Chen, Zhen-Bang; Liu, Kui; Zhang, Fang-Ling; Yuan, Qing; Zhu, Yong-Ming; Organic and Biomolecular Chemistry; vol. 15; nb. 38; (2017); p. 8078 - 8083, View in Reaxys

white

supporting informa- Correa, Arkaitz; Martin, Ruben; Journal of the American Chemical Society; vol. 131; nb. 44; tion (2009); p. 15974 - 15975, View in Reaxys; Sedelmeier, Joerg; Ley, Steven V.; Baxendale, Ian R.; Baumann, Marcus; Organic Letters; vol. 12; nb. 16; (2010); p. 3618 - 3621, View in Reaxys

white

Dam, Johan Hygum; Madsen, Robert; European Journal of Organic Chemistry; nb. 27; (2009); p. 4666 - 4673, View in Reaxys; Patent; METHYLGENE, INC.; WO2005/30704; (2005); (A1) English, View in Reaxys

Dissociation Exponent (3) 1 of 3

Dissociation Group

COOH

Solvent (Dissociation Exponent)

ethanol

Type (Dissociation Exponent)

a1/apparent

Coleman, Tom; Chao, Rebecca R.; Bruning, John B.; De Voss, James J.; Bell, Stephen G.; RSC Advances; vol. 5; nb. 64; (2015); p. 52007 - 52018, View in Reaxys 2 of 3

Comment (Dissociation Exponent)

(pk')pK(a)

Kaszubska,J.; Bal,S.; Roczniki Chemii; vol. 48; (1974); p. 325 - 328, View in Reaxys 3 of 3

Temperature (Dissociation Exponent) [°C]

Type (Dissociation Exponent)

apparent

Comment (Dissociation Exponent)

4.5*1-E5.

Bodforss; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 102; (1922); p. 46, View in Reaxys

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Electrochemical Behaviour (1) Description (Elec- Comment (Electrotrochemical Behav- chemical Behaviour) iour) Electrolytic dissoci- wss. Aethanol. ation / protonation equilibrium

References

Arnold; Bordwell; Journal of the American Chemical Society; vol. 64; (1942); p. 2983,2985, View in Reaxys

Electrochemical Characteristics (4) 1 of 4

Description (Electrochemical Characteristics)

oxidation potential

Solvent (Electrochemical Characteristics)

FSO3H / SbF5

Temperature (Electrochemical Characteristics) [°C]

-76

Rudenko; Pragst; Russian Journal of Organic Chemistry; vol. 34; nb. 11; (1998); p. 1589 - 1626, View in Reaxys 2 of 4

Description (Electrochemical Characteristics)

oxidation potential

Solvent (Electrochemical Characteristics)

acetic acid; fluorosulfonic acid

Temperature (Electrochemical Characteristics) [°C]

-76

Rudenko; Pragst; Russian Journal of Organic Chemistry; vol. 34; nb. 11; (1998); p. 1589 - 1626, View in Reaxys 3 of 4

Description (Electrochemical Characteristics)

oxidation potential

Solvent (Electrochemical Characteristics)

acetonitrile; various solvent(s)

Temperature (Electrochemical Characteristics) [°C]

Rudenko; Pragst; Russian Journal of Organic Chemistry; vol. 34; nb. 11; (1998); p. 1589 - 1626, View in Reaxys 4 of 4

Description (Electrochemical Characteristics)

polarographic half-wave potential

Lurik et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 45; (1975); p. 2287,2246, View in Reaxys Enthalpy of Combustion (2) Enthalpy of ComTemperature (Enbustion [Jmol-1] thalpy of Combustion) [°C]

Pressure (Enthalpy of Combustion) [Torr]

References

-3.3585E+06

24.99

750.075

Camarillo, E. Adriana; Flores, Henoc; Journal of Chemical Thermodynamics; vol. 38; nb. 11; (2006); p. 1269 - 1273, View in Reaxys

-3.3595E+06

24.94

750.075

Matos, M. Agostinha R.; Monte, Manuel J.S.; Sousa, Clara C.S.; Almeida, Ana R.R.P.; Morais, Victor M.F.; Organic and Biomolecular Chemistry; vol. 2; nb. 6; (2004); p. 908 - 914, View in Reaxys

Enthalpy of Formation (2) Enthalpy of Forma- Temperature (Ention [Jmol-1] thalpy of Formation) [°C]

Pressure (Enthalpy of Formation) [Torr]

References

648300

24.99

750.075

Camarillo, E. Adriana; Flores, Henoc; Journal of Chemical Thermodynamics; vol. 38; nb. 11; (2006); p. 1269 - 1273, View in Reaxys

646100

24.94

750.075

Matos, M. Agostinha R.; Monte, Manuel J.S.; Sousa, Clara C.S.; Almeida, Ana R.R.P.; Morais, Victor M.F.; Organic and Biomolecular Chemistry; vol. 2; nb. 6; (2004); p. 908 - 914, View in Reaxys

Enthalpy of Fusion (1) Enthalpy of Fusion References [Jmol-1]

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30500

Matos, M. Agostinha R.; Monte, Manuel J.S.; Sousa, Clara C.S.; Almeida, Ana R.R.P.; Morais, Victor M.F.; Organic and Biomolecular Chemistry; vol. 2; nb. 6; (2004); p. 908 - 914, View in Reaxys

Further Information (4) Description (FurReferences ther Information) Further information McCredie,R.S. et al.; Australian Journal of Chemistry; vol. 22; (1969); p. 1011 - 1032, View in Reaxys Further information Sawicki et al.; Analytical Chemistry; vol. 34; (1962); p. 1460,1461, View in Reaxys Further information Reio; Journal of Chromatography; vol. 4; (1960); p. 458,459-476; Chem.Abstr.; nb. 18552; (1961), View in Reaxys Further information Burke et al.; Analytical Chemistry; vol. 32; (1960); p. 727, View in Reaxys Liquid/Liquid Systems (MCS) (2) 1 of 2

Description (Liquid/Liquid Distribution between solvent 1 + 2 Systems (MCS)) Solvent (Liquid/Liquid Systems (MCS))

H2O; xylene

Smith; Journal of Physical Chemistry; vol. 25; (1921); p. 231; Journal of Physical Chemistry; vol. 26; (1922); p. 269,270, View in Reaxys 2 of 2

Description (Liquid/Liquid Distribution between solvent 1 + 2 Systems (MCS)) Solvent (Liquid/Liquid Systems (MCS))

H2O; CHCl3

Smith; Journal of Physical Chemistry; vol. 25; (1921); p. 231; Journal of Physical Chemistry; vol. 26; (1922); p. 269,270, View in Reaxys Other Thermochemical Data (1) Description (Other Comment (Other Thermochemical Thermochemical Data) Data)

References

Heat of combustion 804,7 kcal/Mol. at constant volume

Purvis; Journal of the Chemical Society; vol. 125; (1924); p. 416; Pr.Cambridge phil.Soc.; vol. 23; p. 589; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 379, View in Reaxys

Vapour Pressure (1) Vapour Pressure Temperature (Va[Torr] pour Pressure) [°C]

Comment (Vapour Pressure)

References

Diagram exists; Equation: p=(Δm/A0w0t) (2πRT/M)1/2

Matos, M. Agostinha R.; Monte, Manuel J.S.; Sousa, Clara C.S.; Almeida, Ana R.R.P.; Morais, Victor M.F.; Organic and Biomolecular Chemistry; vol. 2; nb. 6; (2004); p. 908 - 914, View in Reaxys

0.223 - 0.889

90.06 - 104.19

NMR Spectroscopy (32) 1 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

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

supporting information

Zhang, Xiao; Zhang, Wen-Zhen; Shi, Ling-Long; Guo, Chun-Xiao; Zhang, Ling-Ling; Lu, Xiao-Bing; Chemical Communications; vol. 48; nb. 50; (2012); p. 6292 - 6294, View in Reaxys; Zheng, Rui; Zhou, Qizhong; Gu, Haining; Jiang, Huajiang; Wu, Jiashou; Jin, Zhengneng; Han, Deman; Dai, Guoliang; Chen, Rener; Tetrahedron Letters; vol. 55; nb. 41; (2014); p. 5671 - 5675, View in Reaxys; Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 - 4610, View in Reaxys; Chen, Zhen-Bang; Liu, Kui; Zhang, Fang-Ling; Yuan, Qing; Zhu, Yong-Ming; Organic and Biomolecular Chemistry; vol. 15; nb. 38; (2017); p. 8078 - 8083, View in Reaxys; Yang, Zhanhui; Luo, Renshi; Zhu, Zhongpeng; Yang, Xuerong; Tang, Weiping; Organometallics; vol. 36; nb. 21; (2017); p. 4095 - 4098, View in Reaxys; Jiang, Xingguo; Ma, Shengming; Synthesis (Germany); vol. 50; nb. 8; (2018); p. 1629 - 1639, View in Reaxys

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2 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

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

supporting information

Zhang, Xiao; Zhang, Wen-Zhen; Shi, Ling-Long; Guo, Chun-Xiao; Zhang, Ling-Ling; Lu, Xiao-Bing; Chemical Communications; vol. 48; nb. 50; (2012); p. 6292 - 6294, View in Reaxys; Zheng, Rui; Zhou, Qizhong; Gu, Haining; Jiang, Huajiang; Wu, Jiashou; Jin, Zhengneng; Han, Deman; Dai, Guoliang; Chen, Rener; Tetrahedron Letters; vol. 55; nb. 41; (2014); p. 5671 - 5675, View in Reaxys; Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 - 4610, View in Reaxys; Yang, Zhanhui; Luo, Renshi; Zhu, Zhongpeng; Yang, Xuerong; Tang, Weiping; Organometallics; vol. 36; nb. 21; (2017); p. 4095 - 4098, View in Reaxys; Jiang, Xingguo; Ma, Shengming; Synthesis (Germany); vol. 50; nb. 8; (2018); p. 1629 - 1639, View in Reaxys 3 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Temperature (NMR Spectroscopy) [°C]

22.94

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

supporting information

Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Shashikanth, Sheena; Advanced Synthesis and Catalysis; vol. 359; nb. 3; (2017); p. 419 - 425, View in Reaxys 4 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Temperature (NMR Spectroscopy) [°C]

23.84

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

supporting information

Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Shashikanth, Sheena; Advanced Synthesis and Catalysis; vol. 359; nb. 3; (2017); p. 419 - 425, View in Reaxys 5 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Temperature (NMR Spectroscopy) [°C]

24.84

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

supporting information

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Ovian, John M.; Kelly, Christopher B.; Pistritto, Vincent A.; Leadbeater, Nicholas E.; Organic Letters; vol. 19; nb. 6; (2017); p. 1286 - 1289, View in Reaxys 6 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Temperature (NMR Spectroscopy) [°C]

24.84

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

supporting information

Ovian, John M.; Kelly, Christopher B.; Pistritto, Vincent A.; Leadbeater, Nicholas E.; Organic Letters; vol. 19; nb. 6; (2017); p. 1286 - 1289, View in Reaxys 7 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Huang, Xiaobo; Zhang, Bingchuan; Xu, Hui; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 18; (2017); p. 4336 4340, View in Reaxys 8 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Frequency (NMR Spectro- 101 scopy) [MHz] Location

supporting information

Chen, Zhen-Bang; Liu, Kui; Zhang, Fang-Ling; Yuan, Qing; Zhu, Yong-Ming; Organic and Biomolecular Chemistry; vol. 15; nb. 38; (2017); p. 8078 - 8083, View in Reaxys 9 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectro- 300.1 scopy) [MHz] Location

supporting information

Gianetti, Thomas L.; Annen, Samuel P.; Santiso-Quinones, Gustavo; Reiher, Markus; Driess, Matthias; Grützmacher, Hansjörg; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1854 - 1858; Angew. Chem.; vol. 128; nb. 5; (2015); p. 1886 - 1890,5, View in Reaxys

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10 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectro- 75.5 scopy) [MHz] Location

supporting information

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectro- 500 scopy) [MHz] Location

supporting information

Liu, Mingxin; Li, Chao-Jun; Angewandte Chemie - International Edition; vol. 55; nb. 36; (2016); p. 10806 - 10810; Angew. Chem.; vol. 128; (2016); p. 10964 - 10968,4, View in Reaxys 12 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Temperature (NMR Spectroscopy) [°C]

26.99

Frequency (NMR Spectro- 125 scopy) [MHz] Location

supporting information

Liu, Mingxin; Li, Chao-Jun; Angewandte Chemie - International Edition; vol. 55; nb. 36; (2016); p. 10806 - 10810; Angew. Chem.; vol. 128; (2016); p. 10964 - 10968,4, View in Reaxys 13 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 200 scopy) [MHz] Location

supporting information

Chang, Meng-Yang; Tsai, Chung-Yu; Tetrahedron Letters; vol. 55; nb. 40; (2014); p. 5548 - 5550, View in Reaxys 14 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

d(4)-methanol

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

supporting information

Zhao, Junfeng; Mueck-Lichtenfeld, Christian; Studer, Armido; Advanced Synthesis and Catalysis; vol. 355; nb. 6; (2013); p. 1098 - 1106, View in Reaxys 15 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

deuteromethanol

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

supporting information

Zhao, Junfeng; Mueck-Lichtenfeld, Christian; Studer, Armido; Advanced Synthesis and Catalysis; vol. 355; nb. 6; (2013); p. 1098 - 1106, View in Reaxys 16 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 300 scopy) [MHz] An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS, View in Reaxys 17 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectro- 600 scopy) [MHz] Location

supporting information

Sedelmeier, Joerg; Ley, Steven V.; Baxendale, Ian R.; Baumann, Marcus; Organic Letters; vol. 12; nb. 16; (2010); p. 3618 3621, View in Reaxys 18 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Temperature (NMR Spectroscopy) [°C]

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2018-06-02 11:34:14

Frequency (NMR Spectro- 150 scopy) [MHz] Location

supporting information

Sedelmeier, Joerg; Ley, Steven V.; Baxendale, Ian R.; Baumann, Marcus; Organic Letters; vol. 12; nb. 16; (2010); p. 3618 3621, View in Reaxys 19 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

chloroform-d1

Frequency (NMR Spectro- 400 scopy) [MHz] Hu, Yu Lin; Ma, Xiao Yun; Ge, Qiang; Lu, Ming; Acta Chimica Slovenica; vol. 57; nb. 4; (2010); p. 927 - 930, View in Reaxys 20 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

chloroform-d1

Hu, Yu Lin; Ma, Xiao Yun; Ge, Qiang; Lu, Ming; Acta Chimica Slovenica; vol. 57; nb. 4; (2010); p. 927 - 930, View in Reaxys 21 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

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

supporting information

Dam, Johan Hygum; Madsen, Robert; European Journal of Organic Chemistry; nb. 27; (2009); p. 4666 - 4673, View in Reaxys 22 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

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

supporting information

Dam, Johan Hygum; Madsen, Robert; European Journal of Organic Chemistry; nb. 27; (2009); p. 4666 - 4673, View in Reaxys 23 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

[(2)H6]acetone

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Temperature (NMR Spectroscopy) [°C]

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

supporting information

Correa, Arkaitz; Martin, Ruben; Journal of the American Chemical Society; vol. 131; nb. 44; (2009); p. 15974 - 15975, View in Reaxys 24 of 32

Description (NMR Spectroscopy)

Chemical shifts; Spectrum

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

[(2)H6]acetone

Temperature (NMR Spectroscopy) [°C]

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

supporting information

Correa, Arkaitz; Martin, Ruben; Journal of the American Chemical Society; vol. 131; nb. 44; (2009); p. 15974 - 15975, View in Reaxys 25 of 32

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethyl sulfoxide

Original Text (NMR Spec- NMR: (DMSO) 8 12.72 (br s, 1H), 7.53-7. 50 (m, 1H), 7.34-7. 32 (m, 1H), 6.99-6. 95 (m, 1H), troscopy) 6.10 (s, 2H). Comment (NMR Spectroscopy)

Signals given

Patent; METHYLGENE, INC.; WO2005/30704; (2005); (A1) English, View in Reaxys 26 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

pyridine-d5

Koike, Kazuo; Ohmoto, Taichi; Phytochemistry (Elsevier); vol. 29; nb. 8; (1990); p. 2617 - 2621, View in Reaxys; Ohmoto; Koike; Mitsunaga; Fukuda; Kagei; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 11; (1989); p. 2991 - 2994, View in Reaxys 27 of 32

Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectroscopy)

pyridine-d5

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

pyridine-d5

Comment (NMR Spectroscopy)

1H-1H.

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Description (NMR Spectroscopy)

Chemical shifts

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Buss, Antony D.; Warren, Stuart; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2307 - 2326, View in Reaxys 30 of 32

Description (NMR Spectroscopy)

Spin-spin coupling constants

Solvents (NMR Spectroscopy)

dimethylsulfoxide-d6

Comment (NMR Spectroscopy)

1H-1H

Buss, Antony D.; Warren, Stuart; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2307 - 2326, View in Reaxys 31 of 32

Description (NMR Spectroscopy)

NMR

Description (NMR Spectroscopy)

Spectrum

Comment (NMR Spectroscopy)

1H-

Santavy et al.; Acta Univ. Palack. Olomuc. Suppl. XIII; p. 90 - 114, View in Reaxys IR Spectroscopy (10) 1 of 10

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Jiang, Xingguo; Ma, Shengming; Synthesis (Germany); vol. 50; nb. 8; (2018); p. 1629 - 1639, View in Reaxys 2 of 10

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Zhang, Xiao; Zhang, Wen-Zhen; Shi, Ling-Long; Guo, Chun-Xiao; Zhang, Ling-Ling; Lu, Xiao-Bing; Chemical Communications; vol. 48; nb. 50; (2012); p. 6292 - 6294, View in Reaxys 3 of 10

Description (IR Spectroscopy)

ATR-FTIR (attenuated total reflectance Fourier transform infrared spectroscopy); Bands

Location

supporting information

Comment (IR Spectroscopy)

neat (no solvent, solid phase)

Sedelmeier, Joerg; Ley, Steven V.; Baxendale, Ian R.; Baumann, Marcus; Organic Letters; vol. 12; nb. 16; (2010); p. 3618 3621, View in Reaxys 4 of 10

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Dam, Johan Hygum; Madsen, Robert; European Journal of Organic Chemistry; nb. 27; (2009); p. 4666 - 4673, View in Reaxys

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5 of 10

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

2650 - 1670 cm**(-1)

Buss, Antony D.; Warren, Stuart; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2307 - 2326, View in Reaxys 6 of 10

Description (IR Spectroscopy)

Abe; Yahara; Kubo; et al.; Chemical and Pharmaceutical Bulletin; vol. 22; nb. 11; (1974); p. 2650 - 2655, View in Reaxys; Lurik et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 45; (1975); p. 2287,2246, View in Reaxys; Lloyd et al.; Journal of the American Chemical Society; vol. 88; (1966); p. 5544,5546, View in Reaxys 7 of 10

Description (IR Spectroscopy)

Bands

Santavy et al.; Acta Univ. Palack. Olomuc. Suppl. XIII; p. 90 - 114, View in Reaxys; Baranova et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 47; (1974); p. 2751,2840,2841, View in Reaxys 8 of 10

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

1408 - 719 cm**(-1)

Briggs et al.; Analytical Chemistry; vol. 29; (1957); p. 904,905, View in Reaxys 9 of 10

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3030 - 719 cm**(-1)

Briggs et al.; Analytical Chemistry; vol. 29; (1957); p. 904,905, View in Reaxys 10 of 10

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1667 - 735 cm**(-1)

Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056, View in Reaxys Mass Spectrometry (9) Description (Mass Location Spectrometry)

References

electron impact (EI); spectrum

Jiang, Xingguo; Ma, Shengming; Synthesis (Germany); vol. 50; nb. 8; (2018); p. 1629 - 1639, View in Reaxys

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

supporting informa- Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Shashikanth, Sheena; Adtion vanced Synthesis and Catalysis; vol. 359; nb. 3; (2017); p. 419 - 425, View in Reaxys

gas chromatograsupporting informa- Ovian, John M.; Kelly, Christopher B.; Pistritto, Vincent A.; Leadbeater, Nicholas E.; Organphy mass spectrom- tion ic Letters; vol. 19; nb. 6; (2017); p. 1286 - 1289, View in Reaxys etry (GCMS); electron impact (EI); spectrum electron impact (EI); spectrum

supporting informa- Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; tion (2016); p. 4605 - 4610, View in Reaxys

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HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); TOFMS (Time of flight mass spectrum); Negative ion spectroscopy; Spectrum

supporting informa- Zhang, Xiao; Zhang, Wen-Zhen; Shi, Ling-Long; Guo, Chun-Xiao; Zhang, Ling-Ling; Lu, tion Xiao-Bing; Chemical Communications; vol. 48; nb. 50; (2012); p. 6292 - 6294, View in Reaxys

liquid chromatography mass spectrometry (LCMS); spectrum

Han, Dongfei; Kurusarttra, Somwang; Ryu, Ji-Young; Kanaly, Robert A.; Hur, Hor-Gil; Journal of Agricultural and Food Chemistry; vol. 60; nb. 48; (2012); p. 11972 - 11979, View in Reaxys

TOFMS (Time of flight mass spectrum); ESI (Electrospray ionisation); Spectrum

Chen, Xiaofei; Lou, Ziyang; Zhang, Hai; Tan, Guangguo; Liu, Zhirui; Li, Wuhong; Zhu, Zhenyu; Chai, Yifeng; Rapid Communications in Mass Spectrometry; vol. 25; nb. 11; (2011); p. 1661 - 1674, View in Reaxys

LCMS (Liquid chromatography mass spectrometry); Spectrum

supporting informa- Sedelmeier, Joerg; Ley, Steven V.; Baxendale, Ian R.; Baumann, Marcus; Organic Letters; vol. tion 12; nb. 16; (2010); p. 3618 - 3621, View in Reaxys

fragmentation pattern; electron impact (EI); spectrum

Podda, G.; Maccioni, A.; Fadda, A.; Daolio, S.; Traldi, P.; Vecchi, E.; Organic Mass Spectrometry; vol. 18; nb. 7; (1983); p. 318 - 320, View in Reaxys

UV/VIS Spectroscopy (8) 1 of 8

Description (UV/VIS Spectroscopy)

Spectrum

Santavy et al.; Acta Univ. Palack. Olomuc. Suppl. XIII; p. 46 - 50, View in Reaxys; Coleman, Tom; Chao, Rebecca R.; Bruning, John B.; De Voss, James J.; Bell, Stephen G.; RSC Advances; vol. 5; nb. 64; (2015); p. 52007 - 52018, View in Reaxys 2 of 8

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ VIS) [nm]

216; 258; 296

Koike, Kazuo; Ohmoto, Taichi; Phytochemistry (Elsevier); vol. 29; nb. 8; (1990); p. 2617 - 2621, View in Reaxys 3 of 8

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ VIS) [nm]

216; 258; 296

Ext./Abs. Coefficient [l·mol-1cm-1]

11749; 3802; 3311

Ohmoto; Koike; Mitsunaga; Fukuda; Kagei; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 11; (1989); p. 2991 - 2994, View in Reaxys 4 of 8

Description (UV/VIS Spectroscopy)

UV/VIS

Abe; Yahara; Kubo; et al.; Chemical and Pharmaceutical Bulletin; vol. 22; nb. 11; (1974); p. 2650 - 2655, View in Reaxys; Lurik et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 45; (1975); p. 2287,2246, View in Reaxys; Walterova et al.; Collection of Czechoslovak Chemical Communications; vol. 39; (1974); p. 2449,2451, View in Reaxys 5 of 8

Description (UV/VIS Spectroscopy)

Spectrum

Comment (UV/VIS Spectroscopy)

220 - 335 nm

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Ramart-Lucas; Bulletin de la Societe Chimique de France; vol. <5> 1; (1934); p. 719,727; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 198; (1934); p. 267, View in Reaxys 6 of 8

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Comment (UV/VIS Spectroscopy)

und des Dampfes.

Purvis; Journal of the Chemical Society; vol. 125; (1924); p. 416; Pr.Cambridge phil.Soc.; vol. 23; p. 589; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 379, View in Reaxys 7 of 8

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

ethanol

Dobbie; Lauder; Journal of the Chemical Society; vol. 83; (1903); p. 621, View in Reaxys 8 of 8

Description (UV/VIS Spectroscopy)

Absorption maxima

Santavy et al.; Acta Univ. Palack. Olomuc. Suppl. XIII; p. 46 - 50, View in Reaxys Fluorescence Spectroscopy (1) Description (Fluo- Solvent (Fluoresrescence Spectrocence Spectroscoscopy) py) Maxima Use (1) Use Pattern

Comment (Fluores- References cence Spectroscopy)

acetonitrile; various 357 nm solvent(s)

Schreiber-Deturmeny; Pauli; Pastor; Journal of Pharmaceutical Sciences; vol. 82; nb. 8; (1993); p. 813 - 816, View in Reaxys

References

for agonizing or an- Patent; DEUTSCHES INSTITUT FUeR ERNAeHRUNGSFORSCHUNG; WO2005/102311; (2005); (A1) English, tagonizing View in Reaxys hTAS2R14 function Isolation from Natural Product (6) Isolation from Nat- References ural Product roots of Derris indi- Ranga Rao; Tiwari, Ashok K.; Prabhakar Reddy; Suresh Babu; Ali, Amtul Z.; Madhusudana; Madhusudana ca (Lam.) Bennet; Rao; Bioorganic and Medicinal Chemistry; vol. 17; nb. 14; (2009); p. 5170 - 5175, View in Reaxys collected in Tirumala hills, Chitoor district, Andhra Pradesh, India cold methanol exChen, Yu-Chang; Liao, Chang-Hui; Chen, Ih-Sheng; Phytochemistry; vol. 68; nb. 15; (2007); p. 2101 - 2111, tract of the stems of View in Reaxys Piper philippinum Miq. (Piper kwashoense Hayata) (Piperaceae) collected from Lanyu Island, Taitung County, Taiwan in July 2000 the air-dried rhizomes of Begonia nantoensis Lai and Chung (Begoniaceae) collected from Nanto Hsien, Taiwan, Republic of China, in February 2002

Wu, Pei-Lin; Lin, Fu-Wen; Wu, Tian-Shung; Kuoh, Chang-Sheng; Lee, Kuo-Hsiung; Lee, Shiow-Ju; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 3; (2004); p. 345 - 349, View in Reaxys

aus der Rinde von Xanthoxylum pi-

Abe; Yahara; Kubo; et al.; Chemical and Pharmaceutical Bulletin; vol. 22; nb. 11; (1974); p. 2650 - 2655, View in Reaxys

21/30

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peritum (Abtr. d. Chromat.) In der Paracotorinde

Jobst; Hesse; Justus Liebigs Annalen der Chemie; vol. 199; (1879); p. 73, View in Reaxys

Im CamphergrueOshima; Philippine J. Sci.; vol. 15; p. 368, View in Reaxys noel aus Campherholz (Cinnamomum camphora Nees et Eberm.) Medchem (20) 1 of 20

2 of 20

Target Name

Taste receptor type 2 member 14 [human]

Target Synonyms

t2r14; tas2r14; taste receptor family b member 1; taste receptor type 2 member 14; trb1

Target Uniprot ID

q9nyv8

Target, Subunit, Species

Taste receptor type 2 member 14 [human]

Target Mutant/Chimera Details

Taste receptor type 2 member 14 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Ca2+ mobilisation

Cells/Cell Lines

HEK293T cell line

Substance RN

150206View in Reaxys

Substance Name

piperonylic acid

Substance Dose

1000 µM

Measurement Parameter

stimulation percentage

Qualitative value

Measurement pX

Concomitants: Compound RN

506008

Concomitants: Compound name

DMSO

Concomitants: Compound role

COM

Target Name

Taste receptor type 2 member 14 [human]

Target Synonyms

t2r14; tas2r14; taste receptor family b member 1; taste receptor type 2 member 14; trb1

Target Uniprot ID

q9nyv8

Target, Subunit, Species

Taste receptor type 2 member 14 [human]

Target Mutant/Chimera Details

Taste receptor type 2 member 14 [human]:Wild

Target Species (Bioactivity)

human

Target Transfection

Transfected

Substance Action on Target

Agonist

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Ca2+ mobilisation

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3 of 20

4 of 20

Cells/Cell Lines

HEK293T cell line

Substance RN

150206View in Reaxys

Substance Name

piperonylic acid

Substance Dose

100 µM

Measurement Parameter

stimulation percentage

Qualitative value

Measurement pX

Concomitants: Compound RN

506008

Concomitants: Compound name

DMSO

Concomitants: Compound role

COM

Target Name

Taste receptor type 2 member 14

Target Synonyms

t2r14; tas2r14; taste receptor family b member 1; taste receptor type 2 member 14; trb1

Target, Subunit, Species

Taste receptor type 2 member 14

Target Mutant/Chimera Details

Taste receptor type 2 member 14:Wild

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Effect : TAS2R14 expression; increase ofBioassay : Conditional Expression of hTAS2R14 The cDNA of hTAS2R14 supplemented with an amino terminal export tag corresponding to amino acids 1-45 of rat somatostatin receptor 3 and a carboxy terminal HSV-tag was transiently transfected into HEK-293T cells stably expressing the chimeric G-protein subunit Gal6gust44

Substance RN

150206View in Reaxys

Substance Name

289292

Qualitative Results

title compound at 100-1000 μM increased TAS2R14 expression in dose-dependent manner; figure is given)

Measurement Parameter

qualitative

Substance Effect

Antifeedant

Bioassay Category

In Vivo (Animal models)

Bioassay Name

In vivo Measurement

Bioassay Details

Target : Hylobius abietis (L.), pine weevilBioassay : vehicle control; results expressed as AFIa (antifeedant index) based on feeding area 20 females + 20 males used in two-choice laboratory assay

Substance RN

150206View in Reaxys

Substance Name

289292

Substance Route of Adm.

oral administration

Qualitative Results

title comp. showed AFIa value of 14

Measurement Parameter

qualitative

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

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Bioassay Details

Target : Wistar rat liver microsomesBioassay : TBA: thiobarbituric acid; dl-π-tocopherol with IC50 value of > 1000 μM used as positive control in vitro; effect on NADPH-induced lipid peroxidation assayed; 50 mM potassium phosphate buffer, pH 7.4; 10 μM FeSO4; 20 mM NaCl; NADPH-generating system; 37 deg C; incub. for 7.5 min; lipid peroxidation measured by TBA method

Substance RN

150206View in Reaxys

Substance Name

289292

Measurement Parameter

IC50

Unit

µM

Quantitative value

1000

Measurement pX

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys 6 of 20

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : Wistar rat liver microsomesBioassay : TBA: thiobarbituric acid; dl-π-tocopherol with IC50 value of 22 μM used as positive control in vitro; effect on CCl4-induced lipid peroxidation assayed; 50 mM potassium phosphate buffer, pH 7.4; 3.4 mM CCl4; 20 mM NaCl; 0.6 mM EDTA; NADPH-generating system; 37 deg C; incub. for 7.5 min; lipid peroxidation measured by TBA method

Substance RN

150206View in Reaxys

Substance Name

289292

Measurement Parameter

IC50

Unit

µM

Quantitative value

1000

Measurement pX

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys 7 of 20

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : Wistar rat liver mitochondriaBioassay : dl-π-tocopherol with IC50 value of 16 μM used as positive control in vitro; effect on ascorbate/Fe2+-induced lipid peroxidation assayed; Tris-HCl buffer, pH 7.4; sucrose; 10 μM FeSO4; 40 μM sodium ascorbate; 37 deg C; incub. for 20 min; lipid peroxidation assessed by measuring oxygen uptake

Substance RN

150206View in Reaxys

Substance Name

289292

Measurement Parameter

IC50

Unit

µM

Quantitative value

100

Measurement pX

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys 8 of 20

Substance Effect

Antioxidant

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

In Vitro (others)

Bioassay Details

Target : lecithin liposomesBioassay : TBA: thiobarbituric acid; dl-π-tocopherol with IC50 value of 18 μM used as positive control in vitro; effect on Fe2+-induced lipid peroxidation assayed; 50 mM

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potassium phosphate buffer, pH 7.4; 1 mM FeSO4; 25 deg C; incub. for 60 min; lipid peroxidation measured by TBA method Substance RN

150206View in Reaxys

Substance Name

289292

Measurement Parameter

IC50

Unit

µM

Quantitative value

280

Measurement pX

3.55

Uchida, Mihoko; Nakajin, Shizuo; Toyoshima, Satoshi; Shinoda, Masato; Biological and Pharmaceutical Bulletin; vol. 19; nb. 4; (1996); p. 623 - 626, View in Reaxys 9 of 20

10 of 20

Target Name

Dihydrofolate reductase [human]

Target Synonyms

dhfr; dihydrofolate reductase

Target Uniprot ID

p00374

Target PDB ID

1boz; 1dhf; 1dlr; 1dls; 1drf; 1hfp; 1hfq; 1hfr; 1kms; 1kmv; 1mvs; 1mvt; 1ohj; 1ohk; 1pd8; 1pd9; 1pdb; 1s3u; 1s3v; 1s3w; 1u71; 1u72; 1yho; 2c2s; 2c2t; 2dhf; 2w3a; 2w3b; 2w3m; 3eig; 3f8y; 3f8z; 3f91; 3fs6; 3ghc; 3ghv; 3ghw; 3gi2; 3gyf; 3l3r; 3n0h; 3ntz; 3nu0; 3nxo; 3nxr; 3nxt; 3nxv; 3nxx; 3nxy; 3nzd; 3oaf; 3s3v; 3s7a; 4ddr; 4g95; 4kak; 4kbn; 4kd7; 4keb; 4kfj; 4m6j; 4m6k; 4m6l; 4qhv; 4qjc; 5hpb; 5hqy; 5hqz; 5hsr; 5hsu; 5ht4; 5ht5; 5hui; 5hvb; 5hve

Target, Subunit, Species

Dihydrofolate reductase [human]

Target Mutant/Chimera Details

Dihydrofolate reductase [human]:Wild

Target Species (Bioactivity)

human

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound (dissolved in 10% DMSO) against recombinant human dihydrofolate reductase mediated type II R67 varient using DHF as substrate, in presence of NADPH upon incubation in 50 mM potassium phosphate, pH 7.0

Biological Species/NCBI ID

human

Substance RN

150206View in Reaxys

Qualitative Results

no inhibition

Measurement Parameter

qualitative

Measurement Object

IC50

Concomitants: Compound name

DHF; NADPH

Concomitants: Compound role

SUB; COM

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent DPPH radical scavenging activity of 25 ug/mL compound (dissolved in DMSO) incubated for 30 min in 0.1 M tris-HCl, pH 7.4

Substance RN

150206View in Reaxys

Measurement Parameter

Activity

Unit

Measurement Object

Scavenging activity

Qualitative value

Quantitative value

2.4

Deviation

1.6

Ranga Rao; Tiwari, Ashok K.; Prabhakar Reddy; Suresh Babu; Ali, Amtul Z.; Madhusudana; Madhusudana Rao; Bioorganic and Medicinal Chemistry; vol. 17; nb. 14; (2009); p. 5170 - 5175, View in Reaxys

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11 of 20

Target Name

Alpha-glucosidase [rat]

Target Synonyms

alpha-glucosidase

Target, Subunit, Species

Alpha-glucosidase [rat]

Target Mutant/Chimera Details

Alpha-glucosidase [rat]:Wild

Target Species (Bioactivity)

rat

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro percent inhibition of rat intestinal alpha-glucosidase using p-nitro-phenyl-alpha-D-glucopyranoside (5 mM) substrate incubated for 5 min in 100 mM phosphate buffer, pH 6.8 by 50 ug/mL of the compound dissolved in DMSO

Biological Species/NCBI ID

rat

Cells/Cell Lines

intestine cell

Substance RN

150206View in Reaxys

Measurement Parameter

% Inhibition

Unit

Measurement Object

Percent inhibition

Qualitative value

Quantitative value

18.4

Deviation

2.2

Concomitants: Compound name

p-nitro-phenyl-alpha-D-glucopyranoside (5 mM)

Concomitants: Compound role

COM

Ranga Rao; Tiwari, Ashok K.; Prabhakar Reddy; Suresh Babu; Ali, Amtul Z.; Madhusudana; Madhusudana Rao; Bioorganic and Medicinal Chemistry; vol. 17; nb. 14; (2009); p. 5170 - 5175, View in Reaxys 12 of 20

Target Name

Tyrosinase [Agaricus bisporus]

Target Synonyms

tyrosinase

Target, Subunit, Species

Tyrosinase [Agaricus bisporus]

Target Mutant/Chimera Details

Tyrosinase [Agaricus bisporus]:Wild

Target Species (Bioactivity)

Agaricus bisporus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Biological Species/NCBI ID

Agaricus bisporus

Substance RN

150206View in Reaxys

Substance Name

Table 1, piperonylic acid

Substance Dose

0 mM

Measurement Parameter

IC50

Unit

Quantitative value

0.36

Deviation

0.0200000

Measurement pX

3.44

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13 of 20

14 of 20

Concomitants: Compound RN

2215169

Concomitants: Compound name

(-)-DOPA

Concomitants: Compound role

SUB

Target Name

Tyrosinase [Agaricus bisporus]

Target Synonyms

tyrosinase

Target, Subunit, Species

Tyrosinase [Agaricus bisporus]

Target Mutant/Chimera Details

Tyrosinase [Agaricus bisporus]:Wild

Target Species (Bioactivity)

Agaricus bisporus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Biological Species/NCBI ID

Agaricus bisporus

Substance RN

150206View in Reaxys

Substance Name

Table 1, piperonylic acid

Substance Dose

0 mM

Measurement Parameter

Ki (inhibition constant)

Unit

Quantitative value

0.207

Deviation

0.0290000

Measurement pX

3.68

Concomitants: Compound RN

2215169

Concomitants: Compound name

(-)-DOPA

Concomitants: Compound role

SUB

Target Name

Tyrosinase [Agaricus bisporus]

Target Synonyms

tyrosinase

Target, Subunit, Species

Tyrosinase [Agaricus bisporus]

Target Mutant/Chimera Details

Tyrosinase [Agaricus bisporus]:Wild

Target Species (Bioactivity)

Agaricus bisporus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Biological Species/NCBI ID

Agaricus bisporus

Substance RN

150206View in Reaxys

Substance Name

Table 1, piperonylic acid

Substance Dose

0 mM

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16 of 20

Measurement Parameter

Ki (inhibition constant)

Unit

Quantitative value

0.089

Deviation

0.0130000

Measurement pX

4.05

Concomitants: Compound RN

2215169

Concomitants: Compound name

(-)-DOPA

Concomitants: Compound role

SUB

Target Name

Tyrosinase [Agaricus bisporus]

Target Synonyms

tyrosinase

Target, Subunit, Species

Tyrosinase [Agaricus bisporus]

Target Mutant/Chimera Details

Tyrosinase [Agaricus bisporus]:Wild

Target Species (Bioactivity)

Agaricus bisporus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Biological Species/NCBI ID

Agaricus bisporus

Substance RN

150206View in Reaxys

Substance Name

Table 1, piperonylic acid

Substance Dose

0 mM

Measurement Parameter

Kic

Unit

Quantitative value

0.455

Deviation

0.0180000

Measurement pX

3.34

Concomitants: Compound RN

2215169

Concomitants: Compound name

(-)-DOPA

Concomitants: Compound role

SUB

Target Name

Tyrosinase [Agaricus bisporus]

Target Synonyms

tyrosinase

Target, Subunit, Species

Tyrosinase [Agaricus bisporus]

Target Mutant/Chimera Details

Tyrosinase [Agaricus bisporus]:Wild

Target Species (Bioactivity)

Agaricus bisporus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

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Biological Species/NCBI ID

17 of 20

18 of 20

Agaricus bisporus

Substance RN

150206View in Reaxys

Substance Name

Table 1, piperonylic acid

Substance Dose

2 mM

Measurement Parameter

% Inhibition

Unit

Quantitative value

Measurement pX

2.29

Concomitants: Compound RN

2215169

Concomitants: Compound name

(-)-DOPA

Concomitants: Compound role

SUB

Target Name

Tyrosinase [Agaricus bisporus]

Target Synonyms

tyrosinase

Target, Subunit, Species

Tyrosinase [Agaricus bisporus]

Target Mutant/Chimera Details

Tyrosinase [Agaricus bisporus]:Wild

Target Species (Bioactivity)

Agaricus bisporus

Target Transfection

Non Transfected

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Biological Species/NCBI ID

Agaricus bisporus

Substance RN

150206View in Reaxys

Substance Name

Table 1, piperonylic acid

Substance Dose

0.800000 mM

Measurement Parameter

kinact

Unit

s-1

Quantitative value

0.000302

Concomitants: Compound RN

2215169

Concomitants: Compound name

(-)-DOPA

Concomitants: Compound role

SUB

Target Name

Tyrosinase [Agaricus bisporus]

Target Synonyms

tyrosinase

Target, Subunit, Species

Tyrosinase [Agaricus bisporus]

Target Mutant/Chimera Details

Tyrosinase [Agaricus bisporus]:Wild

Target Species (Bioactivity)

Agaricus bisporus

Target Transfection

Non Transfected

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Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Biological Species/NCBI ID

Agaricus bisporus

Substance RN

150206View in Reaxys

Substance Name

Table 1, piperonylic acid

Substance Dose

0.200000 mM

Measurement Parameter

kinact

Unit

s-1

Quantitative value

0.0004

Concomitants: Compound RN

2215169

Concomitants: Compound name

(-)-DOPA

Concomitants: Compound role

SUB

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

A-549 cell line

Substance RN

150206View in Reaxys

Substance Name

piperonylic acid

Substance Dose

<= 100 μM

Measurement Parameter

% Inhibition

Qualitative value

Not active

Measurement pX

Ferreira-Silva, Guilherme A.; Ortega, Marina M.; Banionis, Marco A.; Garavelli, Graciana Y.; Martins, Felipe T.; Dias, Julia S.M.; Viegas, Cláudio; Oliveira, Jaqueline C. de; Nascimento, Fabio B. do; Doriguetto, Antonio C.; Barbosa, Marilia I.F.; Ionta, Marisa; Toxicology in Vitro; vol. 44; (2017); p. 382 - 391, View in Reaxys 20 of 20

Substance Effect

Antineoplastic

Bioassay Category

Toxicity/Safety Pharmacology

Cells/Cell Lines

A-549 cell line

Substance RN

150206View in Reaxys

Substance Name

piperonylic acid

Substance Dose

<= 100 μM

Measurement Parameter

% Inhibition

Qualitative value

Not active

Measurement pX

30/30

2018-06-02 11:34:14