3,4,5-Trihydroxybenzoic acid (Gallic acid) [C7H6O5] by Asch

Query Query

Results

Date

274 reactions in Reaxys

2018-03-11 18h:31m:43s (EST)

OH O

1. Query

OH HO OH

Search as: As drawn AND (IDE.XRN=2050274)

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OH OH

O O

OH OH

OH O

O O

OH HO OH

HO HO

O HO

Rx-ID: 36582551 View in Reaxys 1/274 Yield

Conditions & References With recombinant Tan410 in aq. phosphate buffer, Time= 0.75h, T= 35 °C , pH= 7, Enzymatic reaction Yao, Jian; Chen, Qing Long; Shen, Ai Xi; Cao, Wen; Liu, Yu Huan; Journal of Molecular Catalysis B: Enzymatic; vol. 95; (2013); p. 55 - 61 View in Reaxys With ammonium nitrate, dipotassium hydrogenphosphate, potassium dihydrogenphosphate, magnesium sulfate in water, Time= 39h, T= 35 °C , Microbiological reaction Sharma, Kanti Prakash; John; Goswami, Pawas; Soni, Manish; Biocatalysis and Biotransformation; vol. 35; nb. 3; (2017); p. 177 - 184 View in Reaxys

OH HO OH

O O

OH O O

OH OH

H HO H

O OH

HO OH

O HO

O O

OHO

O HO O O

Rx-ID: 45113943 View in Reaxys 2/274 Yield

Conditions & References 4.4. Acid hydrolysis of 13 and 14 A solution of 13 in 1N H2SO4 (2 mg in 10 ml) was heated under reflux for 12 h. After cooling, the resulting solution was neutralizedwith saturated aqueous Na2CO3 solution. The precipitates formed were collected by filtration and dissolved in MeOH. The product was identified as ellagic acid (43) by TLC comparison under UV light (254 nm) with an authentic sample on a silica gel TLC plate, and the plate was developed with a mobile phase of EtOAc-tolueneHCO2H (5: 5: 2.5, v/v, Rf 0.30). The filtrate was analyzed by analytical HPLC (solvent system: aqueous 0.1percent HCO2H (A) and MeCN (B), gradient condition: 1percent-10percent B in 20 min, 1 ml/min) to detect chebulic acid (22, tR 7.6 min) and gallic acid (25, tR 14.0 min), which were identified by comparing the retention time with authentic samples. Parallel studies were carried out with 14 (Supplementary information, Fig. S12). With sulfuric acid, water, Time= 12h, Reflux Lee, Dong Young; Kim, Hyun Woo; Yang, Heejung; Sung, Sang Hyun; Phytochemistry; vol. 137; (2017); p. 109 116

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View in Reaxys

OH HO OH

O O

OH O O

H HO H

O O

OHO

HO OH

O O O O

Rx-ID: 45113944 View in Reaxys 3/274 Yield

OH HO

HO HO

O OH

HO OH

OH OH

Rx-ID: 42836025 View in Reaxys 4/274 Yield

Conditions & References With hydrogenchloride in water, Time= 2h, Reflux Yang, Ya-Nan; Li, Fu-Shuang; Liu, Fu; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng; RSC Advances; vol. 6; nb. 65; (2016); p. 60741 - 60748 View in Reaxys OH O OH HO OH

Rx-ID: 7254292 View in Reaxys 5/274 Yield

Conditions & References zur technischen Darstellung Schwyzer,J.;

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View in Reaxys Graesslin,D. et al.; Chemische Berichte; vol. 100; (1967); p. 3077 - 3083 View in Reaxys Shipchandler,M.T. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1975); p. 1400 - 1401 View in Reaxys Faugeras; Annales pharmaceutiques francaises; vol. 29; nb. 4; (1971); p. 241 - 258 View in Reaxys Lakshmi; Chauhan; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 814 View in Reaxys Haslam et al.; Journal of the Chemical Society; (1961); p. 1854,1857 View in Reaxys Singh; Bose; Journal of Scientific and Industrial Research, Section B: Physical Sciences; vol. 20; (1961); p. 296 View in Reaxys Subramanian et al.; Phytochemistry (Elsevier); vol. 8; (1969); p. 673 View in Reaxys Watanabe; Oshima; Agricultural and Biological Chemistry; vol. 29; (1965); p. 90,92 View in Reaxys Zenk; Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,; vol. 19; (1964); p. 83 View in Reaxys 37.B : Step B. Step B. Preparation of N-[Nα-(2,4,6-Trihydroxybenzoyl)-Nε-benzyloxycarbonyl-L-lysyl]dopamine The product obtained in step A of this example (1.7 g, 3.3 mmol) was deprotected according to the indications of general procedure C. The resulting intermediate was coupled with gallic acid (1.0 g, 5.0 mmol) following the indications of general procedure D. The crude material was purified by flash chromatography using a solvent gradient from 20percent to 60percent EtOAc/CH2Cl2. Patent; Pharmacor, Inc.; US6528655; (2003); (B1) English View in Reaxys (c) other herbicidal and related compounds including a carboxylic acid functionality: 2,2-dichloropropionic acid (dalapon), 7-oxabicyclo[2.2.1]heptane 2,3-dicarboxylic acid (endothall), (2,3,6-trichlorophenyl)acetic acid (fenac), glufosinate, gallic acid, gibberellic acid, Patent; Riverdale Chemical Company; US5266553; (1993); (A1) English View in Reaxys applying a pharmaceutically effective amount of a cationic derivative of Minoxidil to said skin, said cationic derivative of Minoxidil formed by mixing solutions of Minoxidil with an organic acid selected from the group consisting of; (R-(R*,R*))-2,3-dihydroxybutanedioic acid (also known as d-tartaric acid); 2,4,6(1H,3H,5H)-pyrimidinetrione (also known as barbituric acid); 3,4-dihydroxybenzoic acid (also known as protocatechuic acid); 2,3,4-trihydroxybenzoic acid; 3,4,5-trihydroxybenzoic acid (also known as gallic acid); 5-nitro-2-furoic acid; 5,5-dimethyloxazolidine-2-4-dione (also known as dimethadione); and Patent; Tulsa Forte Pharmacy Enterprises, Inc.; US5466695; (1995); (A1) English View in Reaxys ...cally effective amount of a cationic derivative of Minoxidil to a positive donor electrode of an iontophoresis apparatus having a negative receiver electrode, said cationic derivative of Minoxidil formed by mixing solutions of Minoxidil with an organic acid selected from the group consisting of: (R-(R*,R*))-2,3-dihydroxybutanedioic acid (also known as d-tartaric acid);

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2. 4,6(1H,3H,5H)-pyrimidinetrione (also known as barbituric acid); 3,4-dihydroxybenzoic acid (also known as protocatechuic acid); 2,3,4-trihydroxybenzoic acid; 3,4,5-trihydroxybenzoic acid (also known as gallic acid); 5-nitro-2-furoic acid; and 5,5-dimethyloxazolidine-2-4-dione (also known as dimethadione); Patent; Tulsa Forte Pharmacy Enterprises, Inc.; US5466695; (1995); (A1) English View in Reaxys A method of claim 4 wherein X is the anion of a compound selected from the following lists of acids: 2,4-dihydroxybenzoic acid; 2,5-dihydroxybenzoic acid; 3,5-dihydroxybenzoic acid; gallic acid; 4-hydroxyisophthalic acid; 2-hydroxynaphthalene-1-carboxylic acid; 6-hydroxynaphthalene-1-carboxylic acid; 5,5'-methylenebis-4-hydroxybenzoic acid; embonic acid; Patent; Hoechst Aktiengesellschaft; US5747484; (1998); (A1) English View in Reaxys 11.h : Extraction Using Supercritical Fluid: h) Dehydro-ellagitannins that yielded gallic acid, egallic acid, valoneic acid lactone, and glucose through hydrolysis. The extract contained in composition C is analyzed by Fourier transform infrared, NMR of 1H (300 MHz), and unidimensional and bidimensional thin layer chromatography, and the following compounds are found: Patent; Valenzuela Cortes, Carmen Maria; US2004/247698; (2004); (A1) English View in Reaxys The combination with antitumoral, antimetastatic and immune response-inducing activity as claimed in claim 1, wherein the compounds of formula II are selected from the group consisting of: 3,4,5-trihydroxybenzoate; methyl 3,4,5-trihydroxybenzoate; ethyl 3,4,5-trihydroxybenzoate; propyl 3,4,5-trihydroxybenzoate; butyl 3,4,5-trihydroxybenzoate; pentyl 3,4,5-trihydroxybenzoate; hexyl 3,4,5-trihydroxybenzoate; heptyl 3,4,5-trihydroxybenzoate; 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoate; ... Patent; PONTIFICIA UNIVERSIDAD JAVERIANA; FIORENTINO, Susana; HERNANDEZ, John Fredy; URUEÑA, Claudia; CASTAÑEDA, Diana; POMBO, Luis Miguel; SANDOVAL, Tito Alejandro; US2015/313925; (2015); (A1) English View in Reaxys OH

O OH HO

OH HO OH

Rx-ID: 21990477 View in Reaxys 6/274 Yield 15 %

Conditions & References With sodium dihydrogenphosphate, Time= 0.25h, T= 25 °C , pH= 7, Glovebox Dhammaraj, Taweesak; Phintha, Aisaraphon; Pinthong, Chatchadaporn; Medhanavyn, Dheeradhach; Tinikul, Ruchanok; Chenprakhon, Pirom; Sucharitakul, Jeerus; Vardhanabhuti, Nontima; Jiarpinitnun, Chutima; Chaiyen, Pimchai; ACS Catalysis; vol. 5; nb. 8; (2015); p. 4492 - 4502

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View in Reaxys Reaction Steps: 2 1: bromine 2: bei der Kalischmelze With bromine Barth; Justus Liebigs Annalen der Chemie; vol. 142; (1867); p. 246; ; (1867); p. 275 View in Reaxys

OH HO

OH O

O OH

OH OH

Rx-ID: 41235838 View in Reaxys 7/274 Yield

Conditions & References Hydrolysis of 1 A solution of 1 (10 mg) in H2O (1 mL) was incubated with tannase (10 U, from Aspergillus ficuum, Sigma, 150 U/g) at 37 °C for 10 h. The resulting mixture was concentrated to dryness in vacuo, dissolved in MeOH (1 mL), and analyzed by HPLC (conditions 1). Gallic acid (tR 3.12 min) was detected in the hydrolysate. Then, the solution was treated with MeI—Na2CO3 (0.5 mL/200 g) at 25 °C for 30 min. The reaction mixture was placed on an SiO2 column (1Χ15 cm) and eluted by CHCl3–MeOH (100:0→50:50) to afford mucic acid dimethyl ester (2.5 mg) that was identified by PMR and 13C NMR data and comparison with a sample prepared by methylation of mucic acid (Aldrich) in an analogous manner. With tannase from Aspergillus ficuum in water, Time= 10h, T= 37 °C , Enzymatic reaction Olennikov; Kashchenko; Schwabl; Vennos; Loepfe; Chemistry of Natural Compounds; vol. 51; nb. 4; (2015); p. 666 - 670; Khim. Prir. Soedin.; nb. 4; (2015); p. 574 - 577,4 View in Reaxys OH

O OH

HO OH

Rx-ID: 37283904 View in Reaxys 8/274 Yield

Conditions & References 2.13 Analysis of the substrate specificity of the P. stutzeri PS59 lipase General procedure: An assay mixture consisting of 1 ml of liquid ester or 1 g of solid ester, 3 ml of isopropanol, 5 ml of phosphate buffer (pH=8.0), and 1 ml of the lipase solution was incubated for 15 min at 30°C with stirring at 180 rpm. The reaction was terminated by the addition of 95percent ethanol, and the amount of liberated fatty acids after incubation was determined by titrating with 50 mM NaOH in the presence of two drops of phenolphthalein solution as the indicator. The control experiment was performed under the same conditions with the addition of 95percent ethanol prior to the reaction. One unit of lipase activity was defined as the amount of enzyme required to liberate 1 μmol of free fatty acid per minute under the experimental conditions. With lipase from Pseudomonas stutzeri PS59 in aq. phosphate buffer, isopropyl alcohol, Time= 0.25h, T= 30 °C , pH= 8, Enzymatic reaction Li, Xiao-Lu; Zhang, Wen-Hui; Wang, Ying-Dong; Dai, Yu-Jie; Zhang, Hui-Tu; Wang, Yue; Wang, Hai-Kuan; Lu, Fu-Ping; Journal of Molecular Catalysis B: Enzymatic; vol. 102; (2014); p. 16 - 24 View in Reaxys

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OH OH

HO O

O O

Rx-ID: 39317550 View in Reaxys 9/274 Yield

Conditions & References With oxygen, T= 20 °C , pH= 10.8, Irradiation, Kinetics Gmurek; Bizukoj; Mosinger; Ledakowicz; Catalysis Today; vol. 240; nb. PA; (2014); p. 160 - 167 View in Reaxys O

OH OH

HO O

O O

Rx-ID: 39317553 View in Reaxys 10/274 Yield

Conditions & References With oxygen, T= 20 °C , pH= 10.8, Irradiation, Kinetics Gmurek; Bizukoj; Mosinger; Ledakowicz; Catalysis Today; vol. 240; nb. PA; (2014); p. 160 - 167 View in Reaxys

OH HO O HO O

OH HO

Rx-ID: 39433617 View in Reaxys 11/274 Yield

Conditions & References With hydrogenchloride, water, Time= 5h, T= 100 °C Nawwar; Youb; El-Raey; Zaghloul; Hashem; Mostafa; Eldahshan; Werner; Becker; Haertel; Lindequist; Linscheid; Pharmazie; vol. 69; nb. 11; (2014); p. 860 - 864 View in Reaxys

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OH OH HO

O OH

HO OH

OH OH

Rx-ID: 19565962 View in Reaxys 12/274 Yield

Conditions & References Reaction Steps: 2 1: 634 mg / 0.02N HCl / ethanol / 1 h 2: H2O / 0.17 h / Ambient temperature; tannase With hydrogenchloride, water in ethanol Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys Reaction Steps: 2 1: 47 mg / 0.01N HCl / ethanol / 3 h / Heating 2: H2O / 0.17 h / tannase With hydrogenchloride, water in ethanol Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys With tannin acyl hydrolase Tan410, recombinant, molecular mass: ca. 55 kDa, Time= 0.666667h, T= 30 °C , pH= 6.4, aq. phosphate buffer, Enzymatic reaction Yao, Jian; Fan, Xin Jiong; Lu, Yi; Liu, Yu Huan; Journal of Agricultural and Food Chemistry; vol. 59; nb. 8; (2011); p. 3812 - 3818 View in Reaxys With recombinant Tan410 in aq. phosphate buffer, Time= 0.75h, T= 35 °C , pH= 7, Enzymatic reaction Yao, Jian; Chen, Qing Long; Shen, Ai Xi; Cao, Wen; Liu, Yu Huan; Journal of Molecular Catalysis B: Enzymatic; vol. 95; (2013); p. 55 - 61 View in Reaxys OH

OH O

HO OH

Rx-ID: 31330610 View in Reaxys 13/274 Yield

Conditions & References With Enterobacter sp. tannase, water, Enzymatic reaction, Kinetics Sharma, Kanti Prakash; John; Process Biochemistry; vol. 46; nb. 1; (2011); p. 240 - 244 View in Reaxys With tannin acyl hydrolase Tan410, recombinant, molecular mass: ca. 55 kDa, Time= 0.666667h, T= 30 °C , pH= 6.4, aq. phosphate buffer, Enzymatic reaction Yao, Jian; Fan, Xin Jiong; Lu, Yi; Liu, Yu Huan; Journal of Agricultural and Food Chemistry; vol. 59; nb. 8; (2011); p. 3812 - 3818 View in Reaxys Stage 1:Time= 0.166667h, T= 37 °C , pH= 6.5, aq. phosphate buffer, Incubation, Enzymatic reaction Stage 2: in methanol, Time= 0.0833333h, T= 30 °C Stage 3: With water, potassium hydoxide in methanol

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Fernandez-Lorente, Gloria; Bolivar, Juan Manuel; Rocha-Martin, Javier; Curiel, Jose A.; Munoz, Rosario; De Las Rivas, Blanca; Carrascosa, Alfonso V.; Guisan, Jose M.; Food Chemistry; vol. 128; nb. 1; (2011); p. 214 217 View in Reaxys Reaction Steps: 2 1: tannase from Lactobacillus plantarum immobilised on glyoxyl-agarose / 25 °C / pH 5 / aq. acetate buffer; Enzymatic reaction 2: water / 25 °C / pH 5 / Enzymatic reaction With water Fernandez-Lorente, Gloria; Bolivar, Juan Manuel; Rocha-Martin, Javier; Curiel, Jose A.; Munoz, Rosario; De Las Rivas, Blanca; Carrascosa, Alfonso V.; Guisan, Jose M.; Food Chemistry; vol. 128; nb. 1; (2011); p. 214 217 View in Reaxys With recombinant Tan410 in aq. phosphate buffer, Time= 0.75h, T= 35 °C , pH= 7, Enzymatic reaction Yao, Jian; Chen, Qing Long; Shen, Ai Xi; Cao, Wen; Liu, Yu Huan; Journal of Molecular Catalysis B: Enzymatic; vol. 95; (2013); p. 55 - 61 View in Reaxys

O O– 2

Ca 2+

O O

HO OH

Rx-ID: 34304451 View in Reaxys 14/274 Yield

Conditions & References

90 %

Stage 1:T= 250 - 300 °C , p= 10 - 15Torr Stage 2:Acidic conditions View in Reaxys

OH HO

OH OH

OH O

HO O

O O

OH HO

Rx-ID: 35556235 View in Reaxys 15/274 Yield

Conditions & References With tannase from A. ficuum in aq. acetate buffer, Time= 6h, T= 38 °C , pH= 5 Olennikov; Chekhirova; Chemistry of Natural Compounds; vol. 49; nb. 1; (2013); p. 1 - 7; Khim. Prir. Soedin.; nb. 1; (2013); p. 5 - 10,6 View in Reaxys

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OH HO

O H HO O

O O

OH O

HO OH

OH OH

H O

Rx-ID: 35556236 View in Reaxys 16/274 Yield

Conditions & References With trifluoroacetic acid, Time= 6h, T= 100 °C Olennikov; Chekhirova; Chemistry of Natural Compounds; vol. 49; nb. 1; (2013); p. 1 - 7; Khim. Prir. Soedin.; nb. 1; (2013); p. 5 - 10,6 View in Reaxys OH

HO HO

Rx-ID: 36241743 View in Reaxys 17/274 Yield

Conditions & References

53 %

With potassium bromate, hydrogenchloride, potassium bromide in water, Time= 12h, Time Sharma; Robert, Alice R.; Research on Chemical Intermediates; vol. 39; nb. 7; (2013); p. 3251 - 3254 View in Reaxys

OH OH HO

O OH O OH

HO OH

OH OH

Rx-ID: 36582552 View in Reaxys 18/274 Yield

O OH

OH O

HO OH

Rx-ID: 36898850 View in Reaxys 19/274 Yield

Conditions & References Determination of aldose configuration Determination of aldose configuration A solution of 2 (0.5 mg) in 0.5 M HCl (0.3 mL) was heated at 90 °C in a screw-capped vial for 2 h.

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Production of gallic acid was confirmed by silica gel TLC [Rf 0.8, toluene:HCO2Et:HCO2H (1:7:1), characteristic blue coloration with FeCl3 reagent] and HPLC analysis (tR 9.8 min). With hydrogenchloride, water, Time= 2h, T= 90 °C Omar, Mohamed; Matsuo, Yosuke; Maeda, Hajime; Saito, Yoshinori; Tanaka, Takashi; Phytochemistry Letters; vol. 6; nb. 3; (2013); p. 486 - 490 View in Reaxys

OH OH OH

O HO

OHOH

OH HO

HO O

Rx-ID: 33880488 View in Reaxys 20/274 Yield

Conditions & References With hydrogenchloride, water in methanol, Time= 2h, T= 90 °C Sun, Jia-Xiang; Zhao, Xiao-Ya; Fu, Xiao-Fang; Yu, Heng-Yi; Li, Xue; Li, Shu-Ming; Ruan, Han-Li; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 6; (2012); p. 785 - 789 View in Reaxys

OH O

OH HO

HO OH

OH OH

O OH

O H

OH OH

Rx-ID: 34199258 View in Reaxys 21/274 Yield

Conditions & References With hydrogenchloride, water, Time= 5h, T= 100 °C View in Reaxys Nawwar, Mahmoud A.; Ayoub, Nahla A.; El-Rai, Mohamed A.; Bassyouny, Fatma; Mostafa, Eman S.; Al-Abd, Ahmed M.; Harms, Manuela; Wende, Kristian; Lindequist, Ulrike; Linscheid, Michael W.; Fitoterapia; vol. 83; nb. 7; (2012); p. 1256 - 1266 View in Reaxys

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OH OH

O OH

OH O

HO O

O H O

O OH

HO OH

OH OH

O H

Rx-ID: 34199259 View in Reaxys 22/274 Yield

Conditions & References With hydrogenchloride, water, Time= 0.25h, T= 100 °C View in Reaxys Nawwar, Mahmoud A.; Ayoub, Nahla A.; El-Rai, Mohamed A.; Bassyouny, Fatma; Mostafa, Eman S.; Al-Abd, Ahmed M.; Harms, Manuela; Wende, Kristian; Lindequist, Ulrike; Linscheid, Michael W.; Fitoterapia; vol. 83; nb. 7; (2012); p. 1256 - 1266 View in Reaxys

OH HO

OH OH

OH HO

HO HO

O HO

OH HO

Rx-ID: 34505528 View in Reaxys 23/274 Yield

Conditions & References Stage 1: With hydrogenchloride, water, Time= 1.5h, T= 105 °C Stage 2: in water Yoshimura, Morio; Yamakami, Saori; Amakura, Yoshiaki; Yoshida, Takashi; Journal of Natural Products; vol. 75; nb. 10; (2012); p. 1798 - 1802 View in Reaxys

HO HO

HO OH HO

O H

O O

HO OH

OH OH

Rx-ID: 35888729 View in Reaxys 24/274 Yield

Conditions & References With sulfuric acid, Time= 2h, T= 90 - 100 °C Huang, Yong-Lin; Tanaka, Takashi; Matsuo, Yosuke; Kouno, Isao; Li, Dian-Peng; Nonaka, Gen-Ichiro; Heterocycles; vol. 86; nb. 1; (2012); p. 381 - 389 View in Reaxys

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OH OH

Rx-ID: 31530597 View in Reaxys 25/274 Yield

Conditions & References With sulfuric acid, water Ballesta-Claver; Valencia; Capitan-Vallvey; Luminescence; vol. 26; nb. 1; (2011); p. 44 - 53 View in Reaxys With tannin acyl hydrolase Tan410, recombinant, molecular mass: ca. 55 kDa, Time= 0.0833333h, T= 30 °C , pH= 6.4, aq. phosphate buffer, Enzymatic reaction Yao, Jian; Fan, Xin Jiong; Lu, Yi; Liu, Yu Huan; Journal of Agricultural and Food Chemistry; vol. 59; nb. 8; (2011); p. 3812 - 3818 View in Reaxys With water, T= 25 °C , pH= 5, Enzymatic reaction Fernandez-Lorente, Gloria; Bolivar, Juan Manuel; Rocha-Martin, Javier; Curiel, Jose A.; Munoz, Rosario; De Las Rivas, Blanca; Carrascosa, Alfonso V.; Guisan, Jose M.; Food Chemistry; vol. 128; nb. 1; (2011); p. 214 217 View in Reaxys

OH O HO HO

O O

OH O

OH OH HO OH

O O

O HO

HO O HO

OH O

O HO HO

OH OH

Rx-ID: 31761975 View in Reaxys 26/274 Yield 53.8 mg, 6.9 mg

Conditions & References 4.5. Pyrolysis of 6 Compound 6 (400 mg) in a flat bottom glass vial (20 mL) washeated at 200 °C for 30 min. The mixture was separated by MCI-gel CHP20P CC (2 cm i.d. .x. 24 cm) with H2O containing increasing proportions of MeOH (0-100percent, 10percent stepwise) to give gallic acid (53.8 mg), pyrogallol (6.9 mg), meta- and para-digallic acid (15) (10.5 mg) and 6 (66.0 mg), and a mixture of a polymeric substance( 46.8 mg). Gallic acid (2 mg) was heated under similar conditions and HPLC analysis of the reaction mixture showed the generation of a small amount of 15. , Time= 0.5h, T= 200 °C Maeda, Hajime; Kakoki, Narumi; Ayabe, Mami; Koga, Yuki; Oribe, Tomoko; Matsuo, Yosuke; Tanaka, Takashi; Kouno, Isao; Phytochemistry; vol. 72; nb. 8; (2011); p. 796 - 803 View in Reaxys

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OH OH O

OH OH

O OH

O HO

HO OH

OH OH

Rx-ID: 32029946 View in Reaxys 27/274 Yield

Conditions & References Stage 1: With sulfuric acid, water, Time= 3h, T= 85 °C Stage 2: in water Yang, Zhi-Gang; Jia, Liu-Nan; Shen, Yan; Ohmura, Atsuko; Kitanaka, Susumu; Molecules; vol. 16; nb. 10; (2011); p. 8305 - 8318 View in Reaxys O

OH O

O OH

Rx-ID: 32585304 View in Reaxys 28/274 Yield 55 %

Conditions & References With tannase from Lactobacillus plantarum immobilised on glyoxyl-agarose, T= 25 °C , pH= 5, aq. acetate buffer, Enzymatic reaction Fernandez-Lorente, Gloria; Bolivar, Juan Manuel; Rocha-Martin, Javier; Curiel, Jose A.; Munoz, Rosario; De Las Rivas, Blanca; Carrascosa, Alfonso V.; Guisan, Jose M.; Food Chemistry; vol. 128; nb. 1; (2011); p. 214 217 View in Reaxys

HO O HO O

OH O

O HO

Rx-ID: 32585305 View in Reaxys 29/274 Yield

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O O

O OH

OH OH

Rx-ID: 29533089 View in Reaxys 30/274 Yield

Conditions & References With hydrogenchloride, water in methanol, Heating Akhtar, Nida; Ali, Mohd.; Alam, Mohd. Sarwar; Natural Product Research; vol. 24; nb. 10; (2010); p. 962 - 972 View in Reaxys

OH OH

HO O

O OH

O HO

HO OH

Rx-ID: 29533090 View in Reaxys 31/274 Yield

Conditions & References With hydrogenchloride, water in methanol, Heating Akhtar, Nida; Ali, Mohd.; Alam, Mohd. Sarwar; Natural Product Research; vol. 24; nb. 10; (2010); p. 962 - 972 View in Reaxys

O O

HO OH

O O

OH HO

HO OH

OH OH

Rx-ID: 29533091 View in Reaxys 32/274 Yield

Conditions & References With hydrogenchloride, water in methanol, Heating Akhtar, Nida; Ali, Mohd.; Alam, Mohd. Sarwar; Natural Product Research; vol. 24; nb. 10; (2010); p. 962 - 972 View in Reaxys

OH OH

O O

HO OH

O O

O OH HO

OH HO OH

OH OH

Rx-ID: 29533092 View in Reaxys 33/274 Yield

Conditions & References With hydrogenchloride, water in methanol, Heating Akhtar, Nida; Ali, Mohd.; Alam, Mohd. Sarwar; Natural Product Research; vol. 24; nb. 10; (2010); p. 962 - 972 View in Reaxys

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HO OH

O O

HO OH

OH OH

Rx-ID: 29533093 View in Reaxys 34/274 Yield

Conditions & References With hydrogenchloride, water in methanol, Heating Akhtar, Nida; Ali, Mohd.; Alam, Mohd. Sarwar; Natural Product Research; vol. 24; nb. 10; (2010); p. 962 - 972 View in Reaxys

OH OH

O O

OH HO

HO OH

Rx-ID: 29533094 View in Reaxys 35/274 Yield

Conditions & References With hydrogenchloride, water in methanol, Heating Akhtar, Nida; Ali, Mohd.; Alam, Mohd. Sarwar; Natural Product Research; vol. 24; nb. 10; (2010); p. 962 - 972 View in Reaxys O

Rx-ID: 29533095 View in Reaxys 36/274 Yield

Conditions & References With hydrogenchloride, water in methanol, Heating Akhtar, Nida; Ali, Mohd.; Alam, Mohd. Sarwar; Natural Product Research; vol. 24; nb. 10; (2010); p. 962 - 972 View in Reaxys

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OH HO

HO OH O

HO O

O OH

OH OH OH HO

OH HO OH

O OH OH OH HO

OH OH

Rx-ID: 29716280 View in Reaxys 37/274 Yield

Conditions & References With water, potassium hydoxide, Heating, Inert atmosphere Alimova; Nishanbaev; Vdovin; Abdullaev; Aripova; Chemistry of Natural Compounds; vol. 46; nb. 3; (2010); p. 352 - 356 View in Reaxys

OH OH

OH O

O OH OH OH HO

OH OH HO

OH HO

OH HO OH

OH OH OH HO

O OH OH OH HO

OH O

OH OH

Rx-ID: 29716286 View in Reaxys 38/274 Yield

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HO O

O OH

HO OH

Rx-ID: 29735455 View in Reaxys 39/274 Yield

Conditions & References 12 : Synthesis of G1 Dendrimers Compound 2 and Compound 3 Example 12 Synthesis of G1 Dendrimers Compound 2 and Compound 3 Two G1 dendrimers, compound 2 and compound 3, were synthesised similar to the scheme for compound 1, as shown in , from vanillin and 5-iodovanillin building blocks, respectively. In , (a) is 4-aminomethylbenzylamine, Na(OAc)3BH, 1,2-dichloroethane; (b) is TBDMS-Cl, triethylamine, CH2Cl2, 0° C.; and (c) is n-Bu4NF, THF. Patent; Lee, Choon Young; US2010/247439; (2010); (A1) English View in Reaxys

OH HO

O OH

HO OH

OH OH

Rx-ID: 31677828 View in Reaxys 40/274 Yield

Conditions & References Time= 7h, T= 120 °C , pH= 5, aq. acetate buffer Lee, Ren-Jye; Lee, Viola S. Y.; Tzen, Jason T. C.; Lee, Maw-Rong; Rapid Communications in Mass Spectrometry; vol. 24; nb. 7; (2010); p. 851 - 858 View in Reaxys

OH OH HO

OH O

OH OH

OH O

HO HO

OH S(a)-isomer

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OH HO

OH OH

O O

HO O

OH HO

O O

OH O

HO OH

OH OH S(a)-isomer

Rx-ID: 28869056 View in Reaxys 41/274 Yield

Conditions & References

1.5 mg, 2 mg

With water, trifluoroacetic acid, Time= 2h, T= 100 °C Liu, Hongwei; Li, Jiankuan; Zhao, Wenhua; Bao, Li; Song, Xiaohong; Xia, Ying; Wang, Xue; Zhang, Chao; Wang, Xiaozhu; Yao, Xinsheng; Li, Ming; Chemistry and Biodiversity; vol. 6; nb. 3; (2009); p. 402 - 410 View in Reaxys

OH OH

O+

Cl –

OH H

OH OH

HO HO

Rx-ID: 29340719 View in Reaxys 42/274 Yield

Conditions & References With water, T= 37 °C , pH= 7.4, aq. phosphate buffer, Kinetics Woodward, Gary; Kroon, Paul; Cassidy, Aedin; Kay, Colin; Journal of Agricultural and Food Chemistry; vol. 57; nb. 12; (2009); p. 5271 - 5278 View in Reaxys

HO HO O

O HO

H HO

O HO

HO OH

Z O

Rx-ID: 28158436 View in Reaxys 43/274 Yield 2.1 mg

Conditions & References Stage 1: With water, Time= 1.5h, T= 30 °C Stage 2: With β-glucosidase, Time= 3h, T= 37 °C Kikuzaki, Hiroe; Miyajima, Yoshiko; Nakatani, Nobuji; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 861 865

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View in Reaxys

HO HO O

OH HO

O HO

O O

O HO

OH OH

O Z O

Rx-ID: 28158437 View in Reaxys 44/274 Yield

Conditions & References With water, Time= 1.5h, T= 30 °C Kikuzaki, Hiroe; Miyajima, Yoshiko; Nakatani, Nobuji; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 861 865 View in Reaxys

HO O

O HO

OH HO

Rx-ID: 28158438 View in Reaxys 45/274 Yield

Conditions & References

2.4 mg

With water, Time= 1h, T= 30 °C Kikuzaki, Hiroe; Miyajima, Yoshiko; Nakatani, Nobuji; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 861 865 View in Reaxys

OH HO

O OH

O O

HO O O

HO O

OH HO

O O

OH HO

OH S(a)-isomer

Rx-ID: 28241234 View in Reaxys 46/274 Yield

Conditions & References With sulfuric acid, water, Time= 8h, Heating Yoshimura, Morio; Ito, Hideyuki; Miyashita, Kyoko; Hatano, Tsutomu; Taniguchi, Shoko; Amakura, Yoshiaki; Yoshida, Takashi; Phytochemistry; vol. 69; nb. 18; (2008); p. 3062 - 3069 View in Reaxys

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OH HO

OH OH

O OH

O O

OH OH

O O

OH O

S(a)-isomer

Rx-ID: 28241235 View in Reaxys 47/274 Yield

OHHO

HO OH

OH OH

O OH

O O

HO O

O O

OH O

OH OH

HO OH

OH O

HO OH

O O

OH O

Rx-ID: 28241236 View in Reaxys 48/274 Yield

OH HO

OH OH

O OH

OH O

O O

O HO

HO OH

OH HO

Rx-ID: 28241237 View in Reaxys 49/274 Yield

Conditions & References With hydrogenchloride, water, Time= 12h, Heating

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Yoshimura, Morio; Ito, Hideyuki; Miyashita, Kyoko; Hatano, Tsutomu; Taniguchi, Shoko; Amakura, Yoshiaki; Yoshida, Takashi; Phytochemistry; vol. 69; nb. 18; (2008); p. 3062 - 3069 View in Reaxys

OH HO

HO HO OH

OH OH

O O

O OH

O O

HO OH

OH OH

O O

HO H

O O

OH OHHO

Rx-ID: 28252000 View in Reaxys 50/274 Yield

Conditions & References With hydrogenchloride, water, Time= 10h Yoshida, Takashi; Ito, Hideyuki; Yoshimura, Morio; Miyashita, Kyoko; Hatano, Tsutomu; Phytochemistry; vol. 69; nb. 18; (2008); p. 3070 - 3079 View in Reaxys

OHHO

O O

H O

O O

H O

O O

HO OH

OHHO

OH O

OHHO

O O

OH OH

O H

OH HO

O O

OHHO

OH HO

OHHO

O OH

HO OH

O O

Rx-ID: 28252001 View in Reaxys 51/274 Yield

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HO HO

OHHO

OH HO

OH O O

H O

O O

O OH

O O

OHHO

OH OHHO

H O

HO HO

OHHO

O OH

HO OH

O O

Rx-ID: 28252002 View in Reaxys 52/274 Yield

HO O O

HO O

HO OHHO

OH HO

OH O

H O

OH OH

O O

H HO

O O

H O O

O O

O H

HO OH

OHHO

H O

O OH

HO OH

O O

O OH OH

OH HO

Rx-ID: 28252003 View in Reaxys 53/274 Yield

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HO OH HO OH

HO O

O HO

OH O

HO HO

OH O

HO OH

Rx-ID: 28326426 View in Reaxys 54/274 Yield

Conditions & References With tannase of Aspergillus niger, water, T= 37 °C , Enzymatic reaction Kasajima, Naoki; Ito, Hideyuki; Hatano, Tsutomu; Yoshida, Takashi; Phytochemistry; vol. 69; nb. 18; (2008); p. 3080 - 3086 View in Reaxys

HO OH HO

HO O

HO HO

O O O

H O

OH OH HO

HO OH HO OH HO

HO OH

OH O

OH HO OH

O O

HO OH

Rx-ID: 28326427 View in Reaxys 55/274 Yield

Conditions & References With tannase of Aspergillus niger, water, Time= 20h, T= 37 °C , Enzymatic reaction Kasajima, Naoki; Ito, Hideyuki; Hatano, Tsutomu; Yoshida, Takashi; Phytochemistry; vol. 69; nb. 18; (2008); p. 3080 - 3086 View in Reaxys

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O O

OH O OH

HO OH

Rx-ID: 28326429 View in Reaxys 56/274 Yield

Conditions & References With tannase of Aspergillus niger, water, Time= 48h, T= 37 °C , Enzymatic reaction Kasajima, Naoki; Ito, Hideyuki; Hatano, Tsutomu; Yoshida, Takashi; Phytochemistry; vol. 69; nb. 18; (2008); p. 3080 - 3086 View in Reaxys

OH OH HO

O OH

OH OH

OH HO

OH OH

O OH

OH OH

O OH

OH OH

H 2N

H 2N OH

Rx-ID: 28674064 View in Reaxys 57/274 Yield 11 mg, 3 mg

Conditions & References With tannase from Aspergillus oryzae, water, Time= 3h, T= 37 °C , Enzymatic reaction Fujii, Hajime; Nakagawa, Takashi; Nishioka, Hiroshi; Sato, Eri; Hirose, Aya; Ueno, Yasuhiro; Sun, Buxiang; Yokozawa, Takako; Nonaka, Gen-Ichiro; Journal of Agricultural and Food Chemistry; vol. 55; nb. 4; (2007); p. 1525 - 1531 View in Reaxys

OH OH

H 2N

OH O

OH OH

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HO HO

OH HO

N OH O

OH O OH

OH O O

HO HO

Rx-ID: 9477013 View in Reaxys 58/274 Yield

Conditions & References

34.7 mg, 24.8 mg, 6.9 mg

Stage 1: With sodium hydrogencarbonate, potassium hexacyanoferrate(III) in water, Time= 0.25h, T= 0 °C Stage 2: With acetic acid in ethanol Tanaka, Takashi; Watarumi, Sayaka; Matsuo, Yosuke; Kamei, Midori; Kouno, Isao; Tetrahedron; vol. 59; nb. 40; (2003); p. 7939 - 7947 View in Reaxys

OH OH HO

O OH

HO OH

OH OH

HO O

OH HO

OH O

HO O

OH O

HO O

OH HO

OH OH

HO O

OH HO

HO O HO

OH OH

OH HO

S(a)-isomer

R(a)-isomer

Rx-ID: 9676172 View in Reaxys 59/274 Yield

Conditions & References in phosphate buffer, Time= 3h, T= 37 °C , pH= 7.0, Product distribution, Further Variations: pH-values, Reagents Hatano, Tsutomu; Kusuda, Miwako; Hori, Mami; Shiota, Sumiko; Tsuchiya, Tomofusa; Yoshida, Takashi; Planta Medica; vol. 69; nb. 11; (2003); p. 984 - 989 View in Reaxys

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OH OH

O HO

O O

HO HO

OH HO

HO O

OH HO

HO O

O HO

OH O

O O

OH HO

Rx-ID: 9844940 View in Reaxys 60/274 Yield

Conditions & References With water, Time= 12h, T= 85 °C Tanaka, Takashi; Fukumori, Masatake; Ochi, Tomoko; Kouno, Isao; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 759 - 763 View in Reaxys

OH HO

O HO

O O

O HO

HO OH

Rx-ID: 10014453 View in Reaxys 61/274 Yield

Conditions & References

0.1 g, 0.052 g

With sulfuric acid, Time= 3h, Heating Kobakhidze; Alaniya; Chemistry of Natural Compounds; vol. 39; nb. 3; (2003); p. 262 - 264 View in Reaxys

HO OH

OH O

HO O H HO

OH O

H HO

O OH

OH OH

HO OH

Rx-ID: 8923758 View in Reaxys 62/274 Yield

Conditions & References

1.2 mg, 6.3 With ammonium hydroxide, Time= 0.5h, T= 20 °C mg Mimaki, Yoshihiro; Fukushima, Masato; Yokosuka, Akihito; Sashida, Yutaka; Furuya, Shigenori; Sakagami, Hiroshi; Phytochemistry; vol. 57; nb. 5; (2001); p. 773 - 779

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View in Reaxys

OH HO

OH OH

OH HO

OH OH

HO HO

OH HO

O HO

HO OH

Rx-ID: 8602595 View in Reaxys 63/274 Yield

Conditions & References With tannase in water, Time= 3h, T= 35 °C , Hydrolysis Wang, Jiang-Nong; Hano, Yoshio; Nomura, Taro; Chen, Ying-Jie; Phytochemistry; vol. 53; nb. 8; (2000); p. 1097 - 1102 View in Reaxys

HO O OH

HO O

HO HO

O HO

O OH

HO O HO

Rx-ID: 8632445 View in Reaxys 64/274 Yield

Conditions & References Acid hydrolysis, Hydrolysis Abdullazhanova; Mavlyanov; Abdullaev; Chemistry of Natural Compounds; vol. 36; nb. 1; (2000); p. 97 - 98 View in Reaxys

OH O

O HO

HO OH

OH OH

Rx-ID: 8656851 View in Reaxys 65/274 Yield 5.5 mg

Conditions & References With tannase, Aspergillus oryzae, water, Time= 3h, T= 30 °C , Enzymatic reaction, Hydrolysis Kikuzaki, Hiroe; Sato, Akemi; Mayahara, Yoko; Nakatani, Nobuji; Journal of Natural Products; vol. 63; nb. 6; (2000); p. 749 - 752 View in Reaxys

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OH HO

OH O OH

OH OH

Rx-ID: 8656852 View in Reaxys 66/274 Yield

Conditions & References

2.5 mg

With tannase, Aspergillus oryzae, water, Time= 3h, T= 30 °C , Enzymatic reaction, Hydrolysis Kikuzaki, Hiroe; Sato, Akemi; Mayahara, Yoko; Nakatani, Nobuji; Journal of Natural Products; vol. 63; nb. 6; (2000); p. 749 - 752 View in Reaxys

OH O

HO HO HO

OH OH

O HO

O OH

OH O

OH HO HO

Rx-ID: 8659769 View in Reaxys 67/274 Yield

Conditions & References Acid hydrolysis, Hydrolysis Abdullazhanova; Mavlyanov; Abdullaev; Chemistry of Natural Compounds; vol. 36; nb. 1; (2000); p. 97 - 98 View in Reaxys

OH OH O

OH O

OH OH OH

OH OH

OH HO

HO OH

OH OH HO

O HO

HO OH

OH OH

Rx-ID: 8660711 View in Reaxys 68/274 Yield 370 %

Conditions & References With sodium hydroxide in water, T= 155 - 230 °C , Hydrolysis

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Kuliev; Kim; Vdovin; Abdullaev; Khushbaktova; Syrov; Chemistry of Natural Compounds; vol. 36; nb. 1; (2000); p. 60 - 67 View in Reaxys

OH OH O

O O

OH OH

OH O

HO OH

O HO

O OH

O HO

O OH OH HO

O OH

Rx-ID: 8660729 View in Reaxys 69/274 Yield

Conditions & References

370 %

With sodium hydroxide in water, T= 155 - 230 °C , Hydrolysis Kuliev; Kim; Vdovin; Abdullaev; Khushbaktova; Syrov; Chemistry of Natural Compounds; vol. 36; nb. 1; (2000); p. 60 - 67 View in Reaxys

OH OH

O OH

OH HO OH

Rx-ID: 8683501 View in Reaxys 70/274 Yield

Conditions & References

0.7 %, 62 %

With copper diacetate in water, acetic acid, Time= 36h, T= 40 °C , Oxidation, aromatization Kambourakis, Spiros; Frost; Journal of Organic Chemistry; vol. 65; nb. 21; (2000); p. 6904 - 6909 View in Reaxys With copper diacetate, oxygen, zinc(II) oxide in acetic acid, Time= 14h, T= 50 °C , p= 760.051Torr , Oxidation, aromatization, Kinetics, Product distribution, Further Variations: Reagents Kambourakis, Spiros; Frost; Journal of Organic Chemistry; vol. 65; nb. 21; (2000); p. 6904 - 6909 View in Reaxys

OH O

OH HO

OH OH

Rx-ID: 8744196 View in Reaxys 71/274 Yield

Conditions & References With E.coli RB791 serA, pSK6.234, Time= 14h, Product distribution, Further Variations: other microbials Kambourakis; Draths; Frost; Journal of the American Chemical Society; vol. 122; nb. 37; (2000); p. 9042 - 9043 View in Reaxys

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OH OH

O O

HO OH

Rx-ID: 8613090 View in Reaxys 72/274 Yield

Conditions & References With E. coli, PEP carboxykinase, pKL4.79B plasmid, biofermentation, Product distribution, Further Variations: Reaction partners, Reagents Li, Kai; Frost; Journal of the American Chemical Society; vol. 121; nb. 40; (1999); p. 9461 - 9462 View in Reaxys O

OH OH

O HO

OH HO

Rx-ID: 4468976 View in Reaxys 73/274 Yield

Conditions & References With tannase, water in toluene, T= 20 - 35 °C , ΔrHm o, ΔrGm o, ΔrSm o, reaction time 6-7 d, other reagents: K2HPO4, H3PO4; CH3COONa, CH3COOH; NaOH, 2-(N-morpholino)ethanesulfonic acid; reaction in aq. soln. at various pH, other reaction time, Equilibrium constant, Thermodynamic data Tewari; Schantz; Rekharsky; Goldberg; Journal of Chemical Thermodynamics; vol. 28; nb. 2; (1996); p. 171 - 185 View in Reaxys

OH OH

OH O

OH OH

Rx-ID: 4568094 View in Reaxys 74/274 Yield

Conditions & References

12 % Spectr., 14 % Spectr., 13 %, 3 % Spectr.

With air, Na1.5H1.5PO4, Time= 50h, T= 40 °C , other oxidant, var. time, Rate constant, Mechanism Richman, Jack E.; Chang, Yu-Chen; Kambourakis, Spiros; Draths; Almy, Erick; Snell, Kristi D.; Strasburg, Gale M.; Frost; Journal of the American Chemical Society; vol. 118; nb. 46; (1996); p. 11587 - 11591 View in Reaxys

O O

O OH

HO OH

Rx-ID: 820750 View in Reaxys 75/274 Yield 75 %

Conditions & References With pyridinium hydrobromide perbromide in xylene, Time= 1.5h, Heating Ijaz, A. S.; Alam, M.; Ahmad, B.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 33; (1994); p. 288 - 289 View in Reaxys With hydrogen iodide Heffter; Chemische Berichte; vol. 34; (1901); p. 3014 View in Reaxys

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OH HO O HO

O O

HO OH

O O

OH O

OH HO

OH OH

HO O

O O

O OH

O HO

OH O

OH OH

Rx-ID: 3691170 View in Reaxys 76/274 Yield

Conditions & References With hydrogenchloride, Time= 3h, T= 100 °C , Title compound not separated from byproducts Nawwar; Hussein; Buddrus; Linscheid; Phytochemistry; vol. 35; nb. 5; (1994); p. 1349 - 1354 View in Reaxys

HO HO

O O

HO O O

OH O

OHHO

HO HO

O O

HO OH HO

OH HO

OH OH

O OH OH

O HO

OH HO

O O

Rx-ID: 4009381 View in Reaxys 77/274 Yield

Conditions & References With sulfuric acid, Time= 8h, T= 100 °C

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Yoshida; Nakazawa; Hatano; Yang Rong Chi; Yang Ling Ling; Kun YingYen; Okuda; Phytochemistry; vol. 37; nb. 1; (1994); p. 241 - 244 View in Reaxys

OH HO

OH O

O O

OH HO

O OH

OH HO

O HO

OH HO

O O

OH O OH

O O

OH HO

OH O

HO OH

O HO

Rx-ID: 3083509 View in Reaxys 78/274 Yield

Conditions & References in water, Time= 7h Yoshida; Ahmed; Okuda; Chemical and Pharmaceutical Bulletin; vol. 41; nb. 4; (1993); p. 672 - 679 View in Reaxys

O O

H OH

HO HO

O OH

HO O

O OH HO

HO H

OH HO

H HO

H HO O

O OH

Rx-ID: 3243143 View in Reaxys 79/274 Yield

Conditions & References With sodium hydroxide, Time= 2h, Ambient temperature Romussi; Caviglioli; Pizza; De Tommasi; Archiv der Pharmazie; vol. 326; nb. 9; (1993); p. 525 - 528

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View in Reaxys

OH HO

O HO

HO OH

OH O

OH OH

HO HO

OH O OH

O O

OH HO

OH OH

O OH

OH OH OH

Rx-ID: 3870683 View in Reaxys 80/274 Yield

Conditions & References in water, Time= 5h, T= 40 °C , 2-O-galloyltransferase, citrate buffer, pH 5.0, Yield given Hagenah, Sigrid; Gross, Georg G.; Phytochemistry (Elsevier); vol. 32; nb. 3; (1993); p. 637 - 642 View in Reaxys

OH HO O

OH O

O O

O OH

O HO

O OH

OH O

OHHO

OH O O

O OH

O HO

O O OH

S(a)-isomer

HO HO

OH HO

OH OH HO OH

O HO

OH HO

O O

Rx-ID: 3074590 View in Reaxys 81/274 Yield

Conditions & References With sulfuric acid, Time= 6h, Heating, Title compound not separated from byproducts Yoshida; Haba; Nakata; Okano; Shingu; Okuda; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 1; (1992); p. 66 - 71 View in Reaxys

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OH HO O

OH O

O O

O OH

O HO

O OH

OH OH

O HO HO

OH OHHO

OH O

O O

OH O

O HO

S(a)-isomer

HO HO

OH HO

O O

Rx-ID: 3083045 View in Reaxys 82/274 Yield

OH HO O

OH O

O O

O OH

O HO

O OH

HO O

O HO

OHHO

OH HO

OH O O

OH O

O O

OH O

O HO

S(a)-isomer

HO HO

OH HO

OH HO OH

O HO

OH HO

O O

Rx-ID: 3083072 View in Reaxys 83/274

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Yield

O O

O H OH

O O

H OH

HO OH

O HO

O O H

OH O

OH HO OH

OH O

O O

OH O HO O

Rx-ID: 3083362 View in Reaxys 84/274 Yield

Conditions & References

4 mg, 6 mg in water, Time= 1h, Ambient temperature, tannase Nonaka, Gen-ichiro; Akazawa, Michiko; Nishioka, Itsuo; Heterocycles; vol. 33; nb. 2; (1992); p. 597 - 606 View in Reaxys Rx-ID: 3099012 View in Reaxys 85/274 Yield

Conditions & References

9.2 mg, 5.1 in water, T= 37 °C , tannase prepared from Aspergillus niger, Further byproducts given mg, 3.3 Yoshida; Namba; Lu; Yang; Yen; Okuda; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 2; (1992); p. 338 mg, 13.3 342 mg View in Reaxys

OHHO

OH O O

O O

OH HO

O O

OH O

O O O

OH O

O O

OH OH

O HO OH

O HO

OH HO

O O

O HO OH

O HO

O O

OHHO

OH O

OHHO

HO OH

O OH

O O HO

O O

OH HO

Rx-ID: 3099013 View in Reaxys 86/274

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Yield

Conditions & References

9.2 mg, 1.7 in water, T= 37 °C , tannase prepared from Aspergillus niger, Further byproducts given mg, 5.1 Yoshida; Namba; Lu; Yang; Yen; Okuda; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 2; (1992); p. 338 mg, 13.3 342 mg View in Reaxys

OH HO

HO O

O O

HO O

HO OH

Rx-ID: 3102725 View in Reaxys 87/274 Yield

Conditions & References

4.5 mg, 8.0 With water, Time= 24h, T= 37 °C , tannase mg Sheu, Shiow-Yunn; Hsu, Feng-Lin; Lin, Yu-Chan; Phytochemistry (Elsevier); vol. 31; nb. 7; (1992); p. 2465 - 2468 View in Reaxys

OH O

O HO

HO OH

OH HO

HO O

HO HO

Rx-ID: 3102939 View in Reaxys 88/274 Yield

Conditions & References

3.2 mg, 6.3 With water, Time= 24h, T= 37 °C , tannase mg Sheu, Shiow-Yunn; Hsu, Feng-Lin; Lin, Yu-Chan; Phytochemistry (Elsevier); vol. 31; nb. 7; (1992); p. 2465 - 2468 View in Reaxys

OH HO O

O O

OH OH

OH O

HO OH

HO HO

O O

O HO

O O

OH OH HO

OH OH

Rx-ID: 3189622 View in Reaxys 89/274 Yield

Conditions & References With sulfuric acid, Time= 18h, Heating Yoshida; Maruyama; Nitta; Okuda; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 7; (1992); p. 1750 - 1754

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View in Reaxys

OH OH

OH HO

O O

O HO

O O

OH OH

HO OH

O OH

O HO

O O

OH OH

OH HO

O OH

HO HO

HO OH

O HO

Rx-ID: 3243516 View in Reaxys 90/274 Yield

Conditions & References With sulfuric acid in water, Time= 5h, Heating, other roshenins; also without H2SO4; other time Yoshida; Feng; Okuda; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 8; (1992); p. 1997 - 2001 View in Reaxys

O OH

H HO

HO O

H O

O OH

O O OH

OH O O

OH OH

Rx-ID: 3466254 View in Reaxys 91/274 Yield 2 mg, 10 mg

Conditions & References in water, Time= 3h, Ambient temperature, tannase Tanaka; Tong; Xu; Ishimaru; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 11; (1992); p. 2975 - 2980 View in Reaxys

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OH O OH

HO HO O O

O H

O O

H O

O HO

OH OH

OH O

O OH

OH OH OH

HO OH

Rx-ID: 3467154 View in Reaxys 92/274 Yield

Conditions & References

4 mg, 20 mg

in water, Time= 7h, Ambient temperature, tannase Tanaka; Tong; Xu; Ishimaru; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 11; (1992); p. 2975 - 2980 View in Reaxys

OH HO

HO HO HO OH

H O

OH O

OH OH O

OH OH

O O

HO OH

Rx-ID: 3624563 View in Reaxys 93/274 Yield 2.8 mg, 5 mg

Conditions & References With camphor-10-sulfonic acid in 1,4-dioxane, Time= 12h, Heating Yoshida; Nakata; Hosotani; Nitta; Okuda; Chemical and Pharmaceutical Bulletin; vol. 40; nb. 7; (1992); p. 1727 1732 View in Reaxys

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OH OH

HO HO HO

OH O

O O

OH OH

OH HO

O O

HO O

O OH

OH OH

O OH

O O

OH HO

OH HO HO

HO HO

O OH

OH OH

OH O

O OH

OH OH

HO HO

O O

OH O

O OH

OH HO

Rx-ID: 2769146 View in Reaxys 94/274 Yield

Conditions & References in water, Time= 25h, Heating, Yield given. Yields of byproduct given Yoshida; Chou; Matsuda; Yasuhara; Yazaki; Hatano; Nitta; Okuda; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 5; (1991); p. 1157 - 1162 View in Reaxys

OH HO

OH OH

OH O

OH OH

OH HO OH

H H

OH O

HO HO

Rx-ID: 2785439 View in Reaxys 95/274

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Yield

Conditions & References

8 mg

in water, Time= 1h, Ambient temperature, tannase Nonaka; Sakai; Mihashi; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 4; (1991); p. 884 - 888 View in Reaxys

8 mg, 20 mg

With tannase in water, Time= 3h, Ambient temperature, Product distribution Tanaka; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 2; (1986); p. 656 - 663 View in Reaxys

O O

HO O

O O O

OH O

HO O

O O

OH HO

Rx-ID: 2315059 View in Reaxys 96/274 Yield

Conditions & References enzymatic hydrolysis with tannase Nonaka, Gen-ichiro; Mihashi, Kunihide; Nishioka, Itsuo; Journal of the Chemical Society, Chemical Communications; nb. 11; (1990); p. 790 - 791 View in Reaxys

OH HO

HO O

O O

HO HO

Rx-ID: 2468192 View in Reaxys 97/274 Yield

Conditions & References

4 mg

With tannase in water, Time= 17h, T= 37 °C Hatano, Tsutomu; Yasuhara, Taeko; Abe, Ryoko; Okuda, Takuo; Phytochemistry (Elsevier); vol. 29; nb. 9; (1990); p. 2975 - 2978 View in Reaxys

OH OH

O O

OH HO

HO OH

HO HO HO

O O

O OO

O O HO

OH O

HO HO

Rx-ID: 2471083 View in Reaxys 98/274 Yield 50 mg, 35 mg

Conditions & References With water, tannase, Time= 3h, Ambient temperature

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Nishizawa, Kyoko; Nakata, Isao; Kishida, Atsushi; Ayer, William A.; Browne, Lois M.; Phytochemistry (Elsevier); vol. 29; nb. 8; (1990); p. 2491 - 2494 View in Reaxys

OH OH HO

O OH

O OH O

OH OH

Rx-ID: 1781148 View in Reaxys 99/274 Yield

Conditions & References With tannase in water, Time= 2h, T= 37 °C Yazaki, Kazufumi; Shida, Shoko; Okuda, Takuo; Phytochemistry (Elsevier); vol. 28; nb. 2; (1989); p. 607 - 610 View in Reaxys

O HO O

O O OH

OH OH

O O

OH HO

HO OH

O O O

HO OH

OH HO

Rx-ID: 2521413 View in Reaxys 100/274 Yield

Conditions & References

5 mg, 20 mg

in water, Time= 15h, T= 37 °C , tannase Okuda, Takuo; Yoshida, Takashi; Ashida, Mariko; Yazaki, Kazufumi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 8; (1983); p. 1765 - 1772 View in Reaxys in water, Time= 0.5h, Ambient temperature, tannase Nonaka, Gen-ichiro; Ishimatsu, Makoto; Ageta, Masayuki; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 1; (1989); p. 50 - 53 View in Reaxys

HO O HO

OH O

H O

O OH

HO HO

OH HO

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HO O

O O

HO OH

O OH

HO HO

Rx-ID: 2785546 View in Reaxys 101/274 Yield

Conditions & References

40 mg

in water, Time= 0.583333h, Ambient temperature, tannase, Title compound not separated from byproducts Nonaka, Gen-ichiro; Ishimatsu, Makoto; Ageta, Masayuki; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 1; (1989); p. 50 - 53 View in Reaxys

HO O HO O

HO OH

HO O

O OH

O HO

HO O

O O

HO OH

O OH

HO HO

Rx-ID: 2805730 View in Reaxys 102/274 Yield

Conditions & References

39 mg

in water, Time= 0.5h, Ambient temperature, tannase, Title compound not separated from byproducts Nonaka, Gen-ichiro; Ishimatsu, Makoto; Ageta, Masayuki; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 1; (1989); p. 50 - 53 View in Reaxys

OH OH

OH O

O HO

O O O

OH OH

OH OH OH OH

O O

OH O

HO HO

Rx-ID: 3105866 View in Reaxys 103/274 Yield

Conditions & References

6 mg, 9 mg With tannase in water, Time= 1h, Ambient temperature Saijo; Nonaka; Nishioka; Chemical and pharmaceutical bulletin; vol. 37; nb. 8; (1989); p. 2063 - 2070

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View in Reaxys

OH HO

OH O

O O

OH OO

O O

HO HO

OH HO

O O

OH O

O O

O OHHOHO

HO HO

OH O

HO O

O O

HO OH

HO O

O OH

HO O O OH HO

O O

Rx-ID: 3126408 View in Reaxys 104/274 Yield

Conditions & References With sulfuric acid, T= 90 °C , Product distribution Ishimatsu, Makoto; Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Nishizawa, Makoto; Yamagishi, Takashi; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 7; (1989); p. 1735 - 1743 View in Reaxys

HO O HO HO OH

O OH

OH HO

O HO

O OH

O HO

O O

O O OH HO

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O O

Rx-ID: 3136585 View in Reaxys 105/274 Yield

HO OH

OH O

O O

O HO

OH O OH

O O

O HO HO OH

OH O

O HO

OH HO

O O OH HO

O O

HO OH

OH HO

OH O

Rx-ID: 3189639 View in Reaxys 106/274 Yield

HO O HO

O OH O

H HO

HO OH

HO O

O OH

O O

OH H OH

O OH

(-)-enantiomer

Rx-ID: 3284447 View in Reaxys 107/274 Yield 43 mg

Conditions & References With water, Time= 0.166667h, Ambient temperature, tannase Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263

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View in Reaxys

OH OH HO

OHO

OH OH

HO OH

OH OH

Rx-ID: 3285272 View in Reaxys 108/274 Yield

Conditions & References

3 mg

With water, Time= 0.166667h, tannase Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys

HO O

O O O OH

HO HO

OH OH

HO HO

O OH

HO OH

HO HO HO

Rx-ID: 3285936 View in Reaxys 109/274 Yield

Conditions & References

5 mg

With water, Time= 0.166667h, tannase Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys

HO OH

OH O

O HO

O OH

HO O

OH OH

OH HO

Rx-ID: 3286037 View in Reaxys 110/274 Yield 6 mg

Conditions & References With water, Time= 0.166667h, tannase Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263

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View in Reaxys

OH HO

OH OH

OH OH O

OH OH

OH HO

Rx-ID: 3286095 View in Reaxys 111/274 Yield

Conditions & References

20 mg

in water, Time= 0.166667h, Ambient temperature, tannase Hashimoto, Fumio; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 1; (1989); p. 77 - 85 View in Reaxys

OH HO

HO O

O HO

HO OH OH

OH OH

HO HO

O O

HO OH

Rx-ID: 3286151 View in Reaxys 112/274 Yield 8 mg

Conditions & References With water, Time= 0.166667h, Ambient temperature, tannase Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys

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HO HO

O O

OH HO

O OH

OH OH

HO HO

HO HO HO

O OH

OH HO

Rx-ID: 3286164 View in Reaxys 113/274 Yield

Conditions & References

7 mg

With water, Time= 0.166667h, Ambient temperature, tannase Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys

OH HO

HO O HO OH HO

H OH O

HO HO

HO OH

O OH

OH OH

H H OH O

HO O

HO HO

O O

HO OH

O O

O OH

OH HO

OH H

HO OH

Rx-ID: 3286454 View in Reaxys 114/274 Yield

Conditions & References

5 mg, 42 mg

With tannase in water, Time= 0.05h, Ambient temperature Nonaka, Gen-ichiro; Ishimaru, Kanji; Azuma, Ryutaro; Ishimatsu, Makoto; Nishioka, Itsuo; Chemical & Pharmaceutical Bulletin; vol. 37; nb. 8; (1989); p. 2071 - 2077 View in Reaxys

OH HO

O HO OH HO

O HO HO

H OH O

OH OH

O OH

HO OH

H HO

O O

OH HO

OH H

H OH O

O O

Rx-ID: 3286455 View in Reaxys 115/274 Yield

Conditions & References

38 mg, 111 With tannase in water, Time= 12h, Ambient temperature mg, 235 Nonaka, Gen-ichiro; Ishimaru, Kanji; Azuma, Ryutaro; Ishimatsu, Makoto; Nishioka, Itsuo; Chemical & Pharmg maceutical Bulletin; vol. 37; nb. 8; (1989); p. 2071 - 2077 View in Reaxys

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HO HO

HO OH

OHHO

O HO

O O

OH O

OH OH

OH HO

HO O

OH O

O O

O HO

HO O

O HO

OH O

O O

OHHO

HO OH

Rx-ID: 3286538 View in Reaxys 116/274 Yield

Conditions & References With sodium hydroxide in water, Time= 48h, T= 60 °C , Product distribution Saijo; Nonaka; Nishioka; Chen; Hwang; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 11; (1989); p. 2940 2947 View in Reaxys

OH HO

OH OH

OH OH OH

O O

HO OH

OH OH

OH HO

Rx-ID: 3287040 View in Reaxys 117/274 Yield

Conditions & References

10 mg

With water, Time= 0.166667h, tannase Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys

OH HO

OH OH

O HO

OH HO

O OH

OH OH HO

Rx-ID: 3287041 View in Reaxys 118/274 Yield 23 mg

Conditions & References With water, Time= 0.166667h, tannase

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Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys

OH OH HO

OH OH

OH HO

Rx-ID: 3287060 View in Reaxys 119/274 Yield

Conditions & References

26 mg

With water, Time= 0.166667h, tannase Hashimoto; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 12; (1989); p. 3255 - 3263 View in Reaxys

HO OH

OH OH

HO O

O HO

OH OH

OH HO

O OH

OH OH

OH HO

Rx-ID: 3287158 View in Reaxys 120/274 Yield

Conditions & References

50 mg

in water, Time= 0.166667h, Ambient temperature, tannase Hashimoto, Fumio; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 1; (1989); p. 77 - 85 View in Reaxys

HO OH

OH OH

HO O

O HO

OH OH

O OH

OH HO

OH OH

OH HO

Rx-ID: 3287160 View in Reaxys 121/274 Yield 120 mg

Conditions & References in water, Time= 0.166667h, Ambient temperature, tannase

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Hashimoto, Fumio; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 1; (1989); p. 77 - 85 View in Reaxys

OH OH

OH HO

O O O

OHO HO

O O

O OH

OH O

OHHO

O OH

OH HO

HO O

OHO

O O

OH HO

OHHO

Rx-ID: 3658062 View in Reaxys 122/274 Yield

Conditions & References With tannase in water, Time= 0.75h, Ambient temperature, Product distribution Ishimatsu, Makoto; Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Phytochemistry; vol. 28; nb. 11; (1989); p. 3179 - 3184 View in Reaxys

OH HO

OH OH

OH O

S HO

OH HO

Rx-ID: 19560259 View in Reaxys 123/274 Yield

Conditions & References Reaction Steps: 2 1: 37 mg / 0.01N HCl / ethanol / 12 h / Heating 2: H2O / 0.17 h / Ambient temperature; tannase With hydrogenchloride in ethanol, water Hashimoto, Fumio; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 1; (1989); p. 77 - 85 View in Reaxys

O HO O

HO OH

Rx-ID: 1823740 View in Reaxys 124/274 Yield 29 mg, 61 mg

Conditions & References With tannase, Time= 0.5h, Ambient temperature, incubation Ageta, Masayuki; Ishimaru, Kanji; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 3; (1988); p. 870 - 876 View in Reaxys

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OH HO

O O

O HO

HO OH

OHO

O OHO

OHHO

OH OH

O O

O HO

OH N

OH HO

HO HO

O OH

O HO HO

OH O OH

O HO

HO HO

O HO

HO HO

HO OH

O O

HO HO

O HO

Rx-ID: 2314226 View in Reaxys 125/274 Yield 4 mg, 15 mg, 4 mg, 2 mg

Conditions & References in water, acetone, Time= 10h, Heating Yoshida, Takashi; Ling Chen; Shingu, Tetsuro; Okuda, Takuo; Chemical & Pharmaceutical Bulletin; vol. 36; nb. 8; (1988); p. 2940 - 2949 View in Reaxys

OH HO

O HO

HO O HO

O HO

Rx-ID: 3171118 View in Reaxys 126/274 Yield 9 mg

Conditions & References With tannase, Time= 2h, Ambient temperature, incubation Ageta, Masayuki; Ishimaru, Kanji; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 3; (1988); p. 870 - 876 View in Reaxys

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HO OH

O HO

O O

O HO

HO HO

HO O

Rx-ID: 3180114 View in Reaxys 127/274 Yield

Conditions & References

7 mg, 14 mg

With tannase, Time= 1h, T= 37 °C , incubation Ageta, Masayuki; Ishimaru, Kanji; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 3; (1988); p. 870 - 876 View in Reaxys

O HO

HO O

O HO

Rx-ID: 3180522 View in Reaxys 128/274 Yield

Conditions & References

10 mg, 14 mg

OH O

OH OH O OH O

OH OH

OH HO

OH OH HO

HO OH

OH OH

Rx-ID: 3184000 View in Reaxys 129/274 Yield 7 mg

Conditions & References With tannase, water, Time= 0.166667h Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 5; (1988); p. 1676 - 1684 View in Reaxys

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O O

OH HO

O OH O

O O

OH HO

Rx-ID: 3185778 View in Reaxys 130/274 Yield 3 mg

HO HO

OH O OH

OH HO O

OH HO

O OH

HO OH

OH O

O HO

HO HO

HO O

O HO

OH O

OH HO

O HO

Rx-ID: 3186990 View in Reaxys 131/274 Yield 20 mg

Conditions & References With tannase, Time= 1h, T= 37 °C , incubation Ageta, Masayuki; Ishimaru, Kanji; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 3; (1988); p. 870 - 876 View in Reaxys

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HO HO

OH O OH

OH O

O O

O HO

OH HO

OH O

O HO

OH O

OH HO

O HO

Rx-ID: 3187102 View in Reaxys 132/274 Yield

Conditions & References

19 mg

With tannase, Time= 3h, T= 37 °C , incubation Ageta, Masayuki; Ishimaru, Kanji; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 3; (1988); p. 870 - 876 View in Reaxys

OH HO

O OH

OH HO

OH HO OH

HO HO

Rx-ID: 3189045 View in Reaxys 133/274 Yield 8 mg

Conditions & References With tannase, water, Time= 0.166667h, Ambient temperature Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 5; (1988); p. 1676 - 1684 View in Reaxys

3 mg

With tannase,H2O, Time= 0.166667h, Ambient temperature Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 5; (1988); p. 1676 - 1684 View in Reaxys

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O HO

OH O

HO O

OH HO

O OH

OH O

OH OH

OH HO

Rx-ID: 3189090 View in Reaxys 134/274 Yield

Conditions & References

8 mg

With tannase, water, Time= 0.166667h, Ambient temperature Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 5; (1988); p. 1676 - 1684 View in Reaxys

HO O

HO O HO

O HO

HO O

OH OH

Rx-ID: 3281819 View in Reaxys 135/274 Yield

Conditions & References

15 mg

With tannase in water, Time= 1h, Ambient temperature Kashiwada, Yoshiki; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Nishizawa, Makoto; Yamagishi, Takashi; Chemical and Pharmaceutical Bulletin; vol. 36; (1988); p. 1545 - 1549 View in Reaxys

OH OH O

OH O

HO OH

O HO

Rx-ID: 3283141 View in Reaxys 136/274 Yield

Conditions & References

2 mg, 5 mg With sulfuric acid in methanol, water, Time= 1h, Heating Yaguchi, Yoshikatsu; Sakurai, Nobuko; Nagai, Masahiro; Inoue, Takao; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 4; (1988); p. 1419 - 1424 View in Reaxys

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OH OH O HO

O OH

HO O

O HO

O O

Rx-ID: 3283142 View in Reaxys 137/274 Yield

Conditions & References

0.5 mg, 2 mg, 5 mg

With tannase (from Aspergillus niger) in water, Time= 4h, T= 37 °C Yaguchi, Yoshikatsu; Sakurai, Nobuko; Nagai, Masahiro; Inoue, Takao; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 4; (1988); p. 1419 - 1424 View in Reaxys

OH OH HO

O OH

HO OH

p-nitroso-diethylaniline salt of/the/ naphthalene-disulfonic acid-(1.5)

OH OH

Rx-ID: 20042502 View in Reaxys 138/274 Yield

Conditions & References Reaction Steps: 2 1: 16 mg / K3Fe(CN)6, NaHCO3 / H2O / 1 h 2: tannase, H2O / 0.17 h With tannase, water, sodium hydrogencarbonate, potassium hexacyanoferrate(III) in water Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 5; (1988); p. 1676 - 1684 View in Reaxys Reaction Steps: 2 1: K3Fe(CN)6, NaHCO3 / H2O / 1 h 2: tannase, H2O / 0.17 h With tannase, water, sodium hydrogencarbonate, potassium hexacyanoferrate(III) in water Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 5; (1988); p. 1676 - 1684 View in Reaxys Reaction Steps: 2 1: K3Fe(CN)6, NaHCO3 / H2O / 1 h 2: tannase, H2O / 0.17 h / Ambient temperature With tannase, water, sodium hydrogencarbonate, potassium hexacyanoferrate(III) in water Hashimoto, Fumio; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 5; (1988); p. 1676 - 1684 View in Reaxys

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OH HO

H HO

O O

OH HO

O HO

HO OH

O O

OH HO

Rx-ID: 3186099 View in Reaxys 139/274 Yield

Conditions & References With sulfuric acid in water, Time= 6h, T= 90 °C , acid hydrolysis, structure determination Yoshida; Chen; Hatano; Fukushima; Okuda; Chemical and pharmaceutical bulletin; vol. 35; nb. 5; (1987); p. 1817 - 1822 View in Reaxys

HO HO

O OH O

HO HO

O HO

H H O

O O H

H H

O O

OH O OH O

OH OH

HO OH

OH HO

H O

O O

OH HO

OH O

O O H

O OH

OH OH OH

H O

O OH

Rx-ID: 3187142 View in Reaxys 140/274 Yield 5 mg, 15 mg

Conditions & References With tannase in ethanol, water, Time= 2h, T= 37 °C , enzymatic hydrolisis Nonaka,Gen-Ichiro; Ishimaru, Kanji; Watanabe, Michiyo; Nishioka, Itsuo; Yamauchi, Tatsuo; Wan, Alfred S. C.; Chemical and Pharmaceutical Bulletin; vol. 35; nb. 1; (1987); p. 217 - 220 View in Reaxys

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OH HO O

HO O

OH HO

O HO

HO OH

O OH

OH O OH

Rx-ID: 3671691 View in Reaxys 141/274 Yield

Conditions & References With sulfuric acid in water, Time= 4h, T= 100 °C , study of the acid hydrolysis reaction, Product distribution Xin-Min, Chen; Yoshida, Takashi; Hatano, Tsutomu; Fukushima, Makoto; Okuda, Takuo; Phytochemistry (Elsevier); vol. 26; nb. 2; (1987); p. 515 - 518 View in Reaxys

OH HO

OH OH

O O

O OH

OH O

O O O

O O

OH O

Rx-ID: 2496799 View in Reaxys 142/274 Yield

Conditions & References

5 mg, 6.5 mg

With water in methanol, Time= 0.416667h, Ambient temperature Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 3; (1986); p. 1039 - 1049 View in Reaxys

HO OH O HO

OH OH

OH HO O

OH O OH

HO OH

OH HO OH

Rx-ID: 3176409 View in Reaxys 143/274 Yield 15 mg

Conditions & References With water, Time= 2h, Ambient temperature, tannase Kashiwada; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 8; (1986); p. 3237 - 3243 View in Reaxys

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OH OH

O HO

OH HO

Rx-ID: 3177510 View in Reaxys 144/274 Yield

Conditions & References With tannase in water, Time= 0.166667h, Ambient temperature Nonaka; Hashimoto; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 1; (1986); p. 61 - 65 View in Reaxys

O O

O OH

O HO HO HO

OH O

O O OH

Rx-ID: 3180051 View in Reaxys 145/274 Yield

Conditions & References

33 mg

With water, Time= 2h, Ambient temperature, tannase Kashiwada; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 8; (1986); p. 3237 - 3243 View in Reaxys

OHHO

OH O

OH HO

OH OH

OH HO OH

OH O

OH OH

Rx-ID: 3180736 View in Reaxys 146/274 Yield

Conditions & References With tannase in water, Time= 3h, Ambient temperature, Product distribution Tanaka; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 2; (1986); p. 656 - 663 View in Reaxys OH

O HO

OH O

OOH

O OH

HO HO

HO O HO

Rx-ID: 3184584 View in Reaxys 147/274

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Yield

Conditions & References

3 mg, 7 mg With sulfuric acid, Time= 18h, Heating Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 3; (1986); p. 1039 - 1049 View in Reaxys

OH OH HO O

OH HO

OH O O

OH OH

Rx-ID: 3184587 View in Reaxys 148/274 Yield

Conditions & References

18 mg, 23 mg

With tannase in water, Time= 0.5h, Ambient temperature, Product distribution Tanaka; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 2; (1986); p. 656 - 663 View in Reaxys

OH OH

OH HO

O O

OH OH

Rx-ID: 3185950 View in Reaxys 149/274 Yield

Conditions & References

6 mg, 9 mg With water, Time= 1h, T= 37 °C Nishimura; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 8; (1986); p. 3223 - 3227 View in Reaxys

HO O

O OH

OH O

HO O

OH HO

Rx-ID: 3189198 View in Reaxys 150/274 Yield

Conditions & References With tannase enzym in water, Time= 3h, T= 37 °C , Product distribution

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Tanaka; Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 2; (1986); p. 650 - 655 View in Reaxys

O HO

OH HO

O O

OOH

O O

OH O

HO O

OH OH

OHHO

Rx-ID: 3189376 View in Reaxys 151/274 Yield

Conditions & References

12 mg

in water, Time= 2h, Ambient temperature, tannase Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 3; (1986); p. 1039 - 1049 View in Reaxys

OH O

O OH O

HO H O

H O

OH H O

O OH

OH HO OH

H O

Rx-ID: 3624578 View in Reaxys 152/274 Yield

Conditions & References With tannase in water, Time= 3h, T= 37 °C Nishimura, Hiroaki; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Phytochemistry (Elsevier); vol. 25; nb. 11; (1986); p. 2599 - 2604 View in Reaxys

(+-)-benzoin (1 mol)

OH OH

OH O OH HO

p-nitroso-diethylaniline salt of/the/ naphthalene-disulfonic acid-(1.5)

Rx-ID: 20085493 View in Reaxys 153/274 Yield

Conditions & References Reaction Steps: 2 1: 504 mg / potassium ferricyanide, NaHCO3 / H2O / 1 h 2: tannase / H2O / 0.17 h / Ambient temperature With tannase, sodium hydrogencarbonate, potassium hexacyanoferrate(III) in water

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Nonaka; Hashimoto; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 1; (1986); p. 61 - 65 View in Reaxys

O O

HO O

Rx-ID: 2233608 View in Reaxys 154/274 Yield

Conditions & References

40 mg, 43 mg

With tannase in water, Time= 3h, T= 37 °C , Product distribution Nonaka, Gen-ichiro; Ageta, Masayuki; Nishioka, Itsuo; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 1; (1985); p. 96 - 101 View in Reaxys

HO O

HO HO

O O

O HO

HO OH

Rx-ID: 2469251 View in Reaxys 155/274 Yield

Conditions & References

7 mg, 13 mg

With water, Time= 120h, T= 37 °C Yoshida, Takashi; Maruyama, Yasuhiko; Memon, M.Usman; Shingu, Tetsuro; Okuda, Takuo; Phytochemistry; vol. 24; nb. 5; (1985); p. 1041 - 1046 View in Reaxys

OH HO

OH OH

OH HO

HO HO

H O

HO OH

O OH

OH O HO

OH O

O O

OH OH

OH O

OHHO OH

OH OH

Rx-ID: 2497545 View in Reaxys 156/274 Yield

Conditions & References With acetate buffer pH 5.4, tannase, Time= 0.833333h, T= 37 °C Nonaka, Gen-ichiro; Nishimura, Hiroaki; Nishioka, Itsuo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 163 - 172 View in Reaxys

4 mg, 39 mg

Time= 48h, T= 37 °C , tannase, 0.1M acetate buffer, pH = 5.4 Okuda, Takuo; Yoshida, Takashi; Ashida, Mariko; Yazaki, Kazufumi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 8; (1983); p. 1765 - 1772 View in Reaxys

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OH O O

OH O

O O

OH O

H O

HO HO

OH HO

Rx-ID: 2521256 View in Reaxys 157/274 Yield

Conditions & References in water, Time= 0.5h, T= 37 °C , tannase Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Journal of Chemical Research, Miniprint; nb. 6; (1985); p. 2001 - 2029 View in Reaxys

OH O OH

H O

OH HO

HO HO

OH HO

Rx-ID: 2521257 View in Reaxys 158/274 Yield

Conditions & References

10 mg

in water, Time= 0.5h, T= 37 °C , tannase Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Journal of Chemical Research, Miniprint; nb. 6; (1985); p. 2001 - 2029 View in Reaxys

4 HO

O HO O

OH O

OH OH

O O

O OH

OH HO OH

OH OH

Rx-ID: 2818431 View in Reaxys 159/274 Yield

Conditions & References With acetate buffer pH 5.4, tannase in water, Time= 0.833333h, T= 37 °C , Yield given. Yields of byproduct given Nonaka, Gen-ichiro; Nishimura, Hiroaki; Nishioka, Itsuo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 163 - 172 View in Reaxys

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OH HO

O O

O HO

OH O

O O

O OH

OH OH

OH OH HO

OH O

O O

OH OH

Rx-ID: 2822690 View in Reaxys 160/274 Yield

HO O

OH HO

O O

OH HO

Rx-ID: 3171859 View in Reaxys 161/274 Yield

Conditions & References

28 mg, 11 mg

OH O HO

O OH

HO OH

OH HO

O OH HO

Rx-ID: 3171873 View in Reaxys 162/274 Yield 78 mg, 37 mg

Conditions & References With tannase in water, Time= 3h, T= 37 °C , Product distribution Nonaka, Gen-ichiro; Ageta, Masayuki; Nishioka, Itsuo; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 1; (1985); p. 96 - 101 View in Reaxys

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OH HO

OH O

O O HO

O OH

O HO

HO OH

O O

OH OH

OH HO

O HO

OH HO

Rx-ID: 3607331 View in Reaxys 163/274 Yield

Conditions & References With sulfuric acid Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Journal of Chemical Research, Miniprint; nb. 6; (1985); p. 2001 - 2029 View in Reaxys

OH HO

OH O

O O HO

O OH

HO OH

O O

OH OH HO

OH OH

OH HO

HO HO

O OH

H O

OH HO

O O

O OH

O O

OH HO OH

O O OH

Rx-ID: 3607425 View in Reaxys 164/274 Yield 12 mg, 6 mg

Conditions & References in water, Time= 40h, Heating

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Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Journal of Chemical Research, Miniprint; nb. 6; (1985); p. 2001 - 2029 View in Reaxys

OH HO

OH O

O O

HO HO

OH OH

O O

O O O

O OH

O O HO

OH OH

OH HO

O HO

OH HO

O HO

Rx-ID: 3618682 View in Reaxys 165/274 Yield

Conditions & References With sulfuric acid Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Journal of Chemical Research, Miniprint; nb. 6; (1985); p. 2001 - 2029 View in Reaxys

OH HO O

O O HO

OH HO OH

O O

HO O

OH HO

Rx-ID: 3625524 View in Reaxys 166/274 Yield 1 mg

Conditions & References With sulfuric acid, Time= 5h, Heating Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Journal of Chemical Research, Miniprint; nb. 6; (1985); p. 2001 - 2029 View in Reaxys

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OH HO O

HO O O HO

O O

O OH O

OH HO OH

O O

OH HO

HO O

OH O OH

O O

HO HO

O O

Rx-ID: 3625525 View in Reaxys 167/274 Yield

Conditions & References in water, Time= 0.25h, T= 37 °C , tannase Tanaka, Takashi; Nonaka, Gen-ichiro; Nishioka, Itsuo; Journal of Chemical Research, Miniprint; nb. 6; (1985); p. 2001 - 2029 View in Reaxys

HO HO O HO

O OH

O O

HO OH

OH OH

Rx-ID: 1753010 View in Reaxys 168/274 Yield

Conditions & References With hydrogenchloride, Time= 3h, T= 100 °C Nawwar, M.A.M.; Souleman, A.M.A.; Buddrus, J.; Bauer, H.; Linscheid, M.; Tetrahedron Letters; vol. 25; nb. 1; (1984); p. 49 - 52 View in Reaxys With hydrogenchloride, Time= 3h, T= 100 °C Nawwar, M.A.M.; Souleman, A.M.A.; Buddrus, J.; Bauer, H.; Linscheid, M.; Tetrahedron Letters; vol. 25; nb. 1; (1984); p. 49 - 52 View in Reaxys

HO HO

OH OH

Rx-ID: 1829683 View in Reaxys 169/274

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Yield

Conditions & References With tannase in water, Time= 1.5h, T= 37 °C , hydrolysis of other O-galloyl-D-hamameloses Nonaka, Gen-ichiro; Ishimaru, Kanji; Tanaka, Takashi; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 2; (1984); p. 483 - 489 View in Reaxys

70 mg

With tannase in water, Time= 1.5h, T= 37 °C Nonaka, Gen-ichiro; Ishimaru, Kanji; Tanaka, Takashi; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 2; (1984); p. 483 - 489 View in Reaxys OH

O O

HO OH

Rx-ID: 2161556 View in Reaxys 170/274 Yield

Conditions & References With hydrogen iodide, acetic anhydride, Time= 0.5h, T= 145 °C Nawwar, M.A.M.; Souleman, A.M.A.; Buddrus, J.; Bauer, H.; Linscheid, M.; Tetrahedron Letters; vol. 25; nb. 1; (1984); p. 49 - 52 View in Reaxys

HO OH

O HO

Rx-ID: 2978694 View in Reaxys 171/274 Yield

Conditions & References With tannase, water, Time= 1.5h, T= 37 °C Tanaka, Takashi; Nonaka Gen-Ichiro; Nishioka Itsuo; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 117 - 121 View in Reaxys

HO HO

O O

HO O

HO HO

O OH

HO HO HO

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OH HO HO

O O

O HO

HO OH

O O

Rx-ID: 3147589 View in Reaxys 172/274 Yield

Conditions & References in sulfuric acid, water, Time= 4h, T= 100 °C Okuda; Hatano; Ogawa; et al.; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 11; (1984); p. 4662 - 4665 View in Reaxys

O HO

OH HO

Rx-ID: 3151977 View in Reaxys 173/274 Yield

Conditions & References With tannase, water, Time= 0.5h, Ambient temperature, Product distribution Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3461 - 3470 View in Reaxys

HO O

O HO

OH O

OH HO

Rx-ID: 3167765 View in Reaxys 174/274 Yield 3 mg

Conditions & References With tannase, water, Time= 0.5h, Ambient temperature Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3461 - 3470 View in Reaxys With tannase, water, Time= 0.5h, Ambient temperature Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3461 - 3470 View in Reaxys With tannase, water, Time= 0.5h, Product distribution Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3461 - 3470 View in Reaxys

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OH HO

O O

OH O E

Rx-ID: 3171818 View in Reaxys 175/274 Yield

Conditions & References

21 mg

With tannase, water, Time= 0.5h, T= 37 °C Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3461 - 3470 View in Reaxys

OH HO

O O

O O HO

O HO

Rx-ID: 3172522 View in Reaxys 176/274 Yield 20 mg

Conditions & References With tannase, water, Time= 0.25h, Ambient temperature Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3461 - 3470 View in Reaxys

HO O HO O HO

O HO

OH HO

HO OH

Rx-ID: 3174011 View in Reaxys 177/274 Yield

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O HO

HO O HO

Rx-ID: 3174715 View in Reaxys 178/274 Yield

Conditions & References With tannase, water, Time= 1h, T= 37 °C Tanaka, Takashi; Nonaka Gen-Ichiro; Nishioka Itsuo; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 117 - 121 View in Reaxys

OH OH

OH O

HO OH

Rx-ID: 3178800 View in Reaxys 179/274 Yield

Conditions & References in water, T= 37 °C , tannase Tanaka, Takashi; Sueyasu, Tokiko; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 7; (1984); p. 2676 - 2686 View in Reaxys

HO O

OH HO

O OH

O O HO

O OH

OH O HO

O E

Rx-ID: 3178980 View in Reaxys 180/274 Yield 12 mg

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OH O

HO O

O HO

O HO OH

Rx-ID: 3181415 View in Reaxys 181/274 Yield

OH O

O O

O HO

O OH HO HO

Rx-ID: 3181417 View in Reaxys 182/274 Yield

OH O

O OH

OH OH

O OH

Rx-ID: 3182952 View in Reaxys 183/274 Yield 60 mg

Conditions & References in water, Time= 0.5h, T= 37 °C , tannnase Tanaka, Takashi; Sueyasu, Tokiko; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 7; (1984); p. 2676 - 2686 View in Reaxys

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OH OH

O OH

HO O

Rx-ID: 3182953 View in Reaxys 184/274 Yield

Conditions & References

13 mg, 40 mg, 10 mg

in water, T= 37 °C , hesperidinase Tanaka, Takashi; Sueyasu, Tokiko; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 7; (1984); p. 2676 - 2686 View in Reaxys

OH OH

O OH

HO HO

O OH

O O

OH OH

Rx-ID: 3183151 View in Reaxys 185/274 Yield

Conditions & References in water, Time= 0.5h, T= 37 °C , tannase Tanaka, Takashi; Sueyasu, Tokiko; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 7; (1984); p. 2676 - 2686 View in Reaxys

OH HO

OH OH

O OH

HO HO

O OH

OH OH

Rx-ID: 3183423 View in Reaxys 186/274 Yield

Conditions & References in water, Time= 1h, T= 37 °C , tannnase Tanaka, Takashi; Sueyasu, Tokiko; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 7; (1984); p. 2676 - 2686 View in Reaxys

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OH HO

OH O

OH HO

HO OH OH

OH HO

O OH

OH OH

Rx-ID: 3185524 View in Reaxys 187/274 Yield

OH HO

O HO

OH HO OH

Rx-ID: 3208991 View in Reaxys 188/274 Yield

Conditions & References With sulfuric acid, water, Time= 3h Tanaka, Takashi; Nonaka Gen-Ichiro; Nishioka Itsuo; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 117 - 121 View in Reaxys

HO O

OH E

O OH

O HO

O HO OH

Rx-ID: 3281802 View in Reaxys 189/274 Yield 33 mg

Conditions & References With tannase in water, Time= 1h, Ambient temperature Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3501 - 3517 View in Reaxys

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HO HO

O O

HO O

O HO

Rx-ID: 3281814 View in Reaxys 190/274 Yield

Conditions & References

23 mg

With tannase in water, Time= 0.5h, Ambient temperature Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3501 - 3517 View in Reaxys

HO O

O O

OH OH

OH OH OH

Rx-ID: 3282473 View in Reaxys 191/274 Yield

Conditions & References

32 mg

With tannase in water, Time= 1h, Ambient temperature Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3501 - 3517 View in Reaxys

OH HO

OH OH

OH O

O O

OH O OH OH

OH HO

O O

OH S(a)-isomer

Rx-ID: 3283309 View in Reaxys 192/274 Yield

Conditions & References With sulfuric acid, Time= 12h, T= 90 °C Nishimura, Hiroaki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 5; (1984); p. 1750 - 1753 View in Reaxys

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OH HO

OH O

O O

OH OH

O O

OH OH

HO OH

S(a)-isomer

Rx-ID: 3285158 View in Reaxys 193/274 Yield

HO O

O HO

OH OH

O OH

OH OH

Rx-ID: 3438076 View in Reaxys 194/274 Yield

Conditions & References

28 mg

With tannase in water, Time= 1h, Heating Kashiwada, Yoshiki; Nonaka, Gen-ichiro; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3501 - 3517 View in Reaxys

28 mg

HO HO O HO

O OH

H HO H H

OH O

H OH

monogalloyl glucose

HO OH

OH OH

Rx-ID: 6729574 View in Reaxys 195/274 Yield

Conditions & References With hydrogenchloride, Time= 3h, T= 100 °C , Product distribution Nawwar, M.A.M.; Souleman, A.M.A.; Buddrus, J.; Bauer, H.; Linscheid, M.; Tetrahedron Letters; vol. 25; nb. 1; (1984); p. 49 - 52 View in Reaxys

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OH OH

OH O

OH HO

OH OH

Rx-ID: 483649 View in Reaxys 196/274 Yield

Conditions & References With potassium hydroxide, Time= 1.5h, T= 130 °C Sagareishvili, T. G.; Alaniya, M. D.; Kemertelidze, E. P.; Chemistry of Natural Compounds; vol. 19; nb. 3; (1983); p. 275 - 278; Khimiya Prirodnykh Soedinenii; vol. 19; nb. 3; (1983); p. 289 - 293 View in Reaxys durch Kalischmelze Perkin; Hummel; Journal of the Chemical Society; vol. 69; (1896); p. 1291 View in Reaxys

HO OH

O HO

OH OH O

O HO

HO O OH

HO OH

O OH OH HO

O OH

OH OH OH

OH HO

Rx-ID: 2470476 View in Reaxys 197/274 Yield

Conditions & References With tannase in water Nonaka, Gen-Ichiro; Muta, Makiko; Nishioka, Itsuo; Phytochemistry (Elsevier); vol. 22; nb. 1; (1983); p. 237 - 242 View in Reaxys

OH HO

OH O

OH O OH HO

HO OH

Rx-ID: 2759240 View in Reaxys 198/274 Yield

Conditions & References With barium dihydroxide, Time= 2h, T= 100 °C Taneyama, Masatoshi; Yoshida, Seiichi; Kobayashi, Michio; Hasegawa, Masao; Phytochemistry (Elsevier); vol. 22; nb. 4; (1983); p. 1053 - 1054 View in Reaxys

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OH O

OH OH

O OH

HO O

OH HO

OH OH

Rx-ID: 2805672 View in Reaxys 199/274 Yield

Conditions & References

3 mg, 3.8 mg

With tannase in water, Time= 0.5h, Ambient temperature Nonaka, Gen-Ichiro; Kawahara, Osamu; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 11; (1983); p. 3906 - 3914 View in Reaxys

OH HO

H O O

OH OH

HO OH

Rx-ID: 3021397 View in Reaxys 200/274 Yield

Conditions & References

6 mg

in water, T= 37 °C , tannase Okuda, Takuo; Yoshida, Takashi; Ashida, Mariko; Yazaki, Kazufumi; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 8; (1983); p. 1765 - 1772 View in Reaxys

OH OH

O HO

O OH

OH OH

Rx-ID: 3187392 View in Reaxys 201/274 Yield 6 mg, 11 mg

Conditions & References With tannase in water, Time= 1h, Ambient temperature Nonaka, Gen-Ichiro; Kawahara, Osamu; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 11; (1983); p. 3906 - 3914 View in Reaxys

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OH HO

O OH

OH OH

Rx-ID: 3187491 View in Reaxys 202/274 Yield

Conditions & References

6 mg, 11 mg

With tannase in water, Time= 1h, Ambient temperature Nonaka, Gen-Ichiro; Kawahara, Osamu; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 11; (1983); p. 3906 - 3914 View in Reaxys

OH OH

O HO HO

OH O HO

OH O

HO O

OH OH

OH HO

Rx-ID: 3188632 View in Reaxys 203/274 Yield

Conditions & References

6.7 mg

With tannase in water, Time= 1h, Ambient temperature Nonaka, Gen-Ichiro; Kawahara, Osamu; Nishioka, Itsuo; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 11; (1983); p. 3906 - 3914 View in Reaxys

HO O HO

OH OH

HO O

OH O

OH HO

HO O

OH OH OH O

OH O

HO O

HO OH

OH HO

OH OH

OH HO

Rx-ID: 3189091 View in Reaxys 204/274 Yield 12 mg, 28 mg

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OH OH

O O

OH HO

OH OH

HO HO

O O

O OH

HO HO

HO HO HO

OH OH

Rx-ID: 3286091 View in Reaxys 205/274 Yield

Conditions & References With tannase in ethanol Nonaka, Gen-Ichiro; Muta, Makiko; Nishioka, Itsuo; Phytochemistry (Elsevier); vol. 22; nb. 1; (1983); p. 237 - 242 View in Reaxys

OH OH O

O O

OH O

OH OH

HO OH

Rx-ID: 3599857 View in Reaxys 206/274 Yield

Conditions & References

12 mg, 32 mg

With sulfuric acid in ethanol, water, Time= 3h, Heating Sakurai, Atsushi; Okumura, Yasuaki; Bulletin of the Chemical Society of Japan; vol. 56; nb. 2; (1983); p. 542 - 544 View in Reaxys

OH OH HO

OH HO OH

Rx-ID: 3623361 View in Reaxys 207/274 Yield 14 mg

Conditions & References With potassium permanganate in acetone, Time= 1h, Ambient temperature Murthy, S. S. N.; Phytochemistry (Elsevier); vol. 22; nb. 6; (1983); p. 1518 - 1520 View in Reaxys

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O O

O–

O O

OH HO

O OH

K+

O OH

O–

K+

OH OH

OH HO

Rx-ID: 3624921 View in Reaxys 208/274 Yield

Conditions & References With tannase in water, Time= 0.5h, T= 37 °C Nonaka, Gen-Ichiro; Muta, Makiko; Nishioka, Itsuo; Phytochemistry (Elsevier); vol. 22; nb. 1; (1983); p. 237 - 242 View in Reaxys

OH HO

O O

O OH OH OH

OH HO

OH OH

Rx-ID: 3672403 View in Reaxys 209/274 Yield

Conditions & References

20 mg, 56 mg

With tannase in water, Time= 6h, T= 40 °C Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo; Phytochemistry (Elsevier); vol. 22; nb. 11; (1983); p. 2575 - 2578 View in Reaxys

O HO

OH O

HO OH

OH O

OH HO

Rx-ID: 18600227 View in Reaxys 210/274 Yield

Conditions & References Reaction Steps: 2 1: HI 2: Ba(OH)2 / 2 h / 100 °C With barium dihydroxide, hydrogen iodide Taneyama, Masatoshi; Yoshida, Seiichi; Kobayashi, Michio; Hasegawa, Masao; Phytochemistry (Elsevier); vol. 22; nb. 4; (1983); p. 1053 - 1054 View in Reaxys

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OH HO O

HO HO

O HO O

N HO

OH O

O O

O OH

OH O

O O

O HO O

OH HO

OHHO

OH HO

HO HO

Rx-ID: 1474167 View in Reaxys 211/274 Yield

Conditions & References With sulfuric acid, 1.) reflux, 7.5 h, 2.) ether, overnight, Yield given. Multistep reaction. Yields of byproduct given Nonaka, Gen-ichiro; Tanaka, Takashi; Nishioka, Itsuo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1982); p. 1067 - 1074 View in Reaxys

OH HO

OH O

OH O O

HO O

OH O

HO OH

Rx-ID: 2242689 View in Reaxys 212/274 Yield

Conditions & References With trifluoroacetic acid in water, Time= 30h, Heating Yoshida, Takashi; Seno, Kaoru; Takama, Yukiko; Okuda, Takuo; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1180 - 1182 View in Reaxys

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O HO

OH O

HO OH

OH OH

Rx-ID: 2242889 View in Reaxys 213/274 Yield

OH OH HO

OH O

O O

O H O

O OO

OH HO

S(a)-isomer

OH HO

Rx-ID: 2520718 View in Reaxys 214/274 Yield

Conditions & References

50 mg

With tannase, water, Time= 2h, T= 37 °C Nonaka, Gen-ichiro; Tanaka, Takashi; Nishioka, Itsuo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1982); p. 1067 - 1074 View in Reaxys

OH HO O

HO HO

O HO O

OH HO

OH O

O O

O OH

OH O

O O

O HO O

OH HO

OHHO

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OH HO

HO O HO

O HO

HO OH

HO HO

OH HO

OH OH

O O OH

O O

S(a)-isomer

HO OH

OH HO

Rx-ID: 3154825 View in Reaxys 215/274 Yield

Conditions & References

58 mg, 67 mg

With water, Time= 42h, Ambient temperature Nonaka, Gen-ichiro; Tanaka, Takashi; Nishioka, Itsuo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1982); p. 1067 - 1074 View in Reaxys

OH OH

OH O

O O

OH HO HO HO

HO HO

O O

OH O O

HO HO HO

O OH

OH O

HO O

OH O

O HO HO

Rx-ID: 3185860 View in Reaxys 216/274 Yield

Conditions & References With tannase, water Nishizawa; Yamagishi; Nonaka; et al.; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 3; (1982); p. 1094 1097 View in Reaxys

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OH OH

OH O

HO O

OH HO

O O

OH HO HO HO

Rx-ID: 3185862 View in Reaxys 217/274 Yield

Conditions & References With water, hydrogen cation Nishizawa; Yamagishi; Nonaka; et al.; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 3; (1982); p. 1094 1097 View in Reaxys

OH HO O

O O

O HO OH OH

O OH

O O

HO OH

OH HO

OH OH

HO O O

O OH

OH O

OH OH O

O O

HO HO

HO OH

OH OH

O O

HO OH

OH HO

OHHO

Rx-ID: 3187191 View in Reaxys 218/274 Yield 4 mg, 11 mg

Conditions & References With tannase, water, Time= 28h, T= 40 °C Nonaka, Gen-ichiro; Tanaka, Takashi; Nishioka, Itsuo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1982); p. 1067 - 1074 View in Reaxys

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OH OH OH

OH OH

O O

OH O

O OH

OH O

OH OH

HO OH

Rx-ID: 3599856 View in Reaxys 219/274 Yield

Conditions & References

10 mg, 45 mg, 75 mg

With sodium carbonate, Time= 18h, Ambient temperature, Mechanism Sakurai, Atsushi; Okada, Kyoji; Okumura, Yasuaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 9; (1982); p. 3051 - 3052 View in Reaxys

10 mg, 45 mg, 75 mg

With sodium carbonate, Time= 18h, Ambient temperature Sakurai, Atsushi; Okada, Kyoji; Okumura, Yasuaki; Bulletin of the Chemical Society of Japan; vol. 55; nb. 9; (1982); p. 3051 - 3052 View in Reaxys

HO O

HO HO

OH O O

O OH

HO OH

HO HO

OH HO

OH OH

Rx-ID: 3625252 View in Reaxys 220/274 Yield

Conditions & References tannase Okuda, Takuo; Yoshida, Takashi; Kuwahara, Masaaki; Memon, M. Usman; Shingu, Tetsuro; Journal of the Chemical Society, Chemical Communications; nb. 2; (1982); p. 163 - 164 View in Reaxys

HO O HO HO HO

O O

O OH

O O

OH OH

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OH O

OH O OH

O O

O HO

OH HO

OH O

Rx-ID: 3976101 View in Reaxys 221/274 Yield

Conditions & References With water, Time= 12h, T= 100 °C , Further byproducts given Gupta, Raj K.; Al-Shafi, Sabah M. K.; Layden, Keith; Haslam, Edwin; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1982); p. 2525 - 2534 View in Reaxys

OH HO

HO OO

HO OH

H O

O O

HO OH

O O

OO HO

O H

HO O

OH HO

Rx-ID: 3976103 View in Reaxys 222/274 Yield

Conditions & References With water, Time= 48h, T= 100 °C , Title compound not separated from byproducts Gupta, Raj K.; Al-Shafi, Sabah M. K.; Layden, Keith; Haslam, Edwin; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 11; (1982); p. 2525 - 2534 View in Reaxys

HO OH

HO O

OH O

O HO

O OH

OH OH

OH HO

OH OH

Rx-ID: 2805299 View in Reaxys 223/274 Yield

Conditions & References With tannase, Time= 1h, T= 37 °C , 0.05 M acetate buffer (pH 5.0) Nonaka, Gen-Ichiro; Nishioka, Itsuo; Nagasawa, Tetsuro; Oura, Hikokichi; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 10; (1981); p. 2862 - 2870 View in Reaxys

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OH O

OH HO

O OH

OH HO

OH OH

Rx-ID: 2805666 View in Reaxys 224/274 Yield

Conditions & References With tannase in water, Time= 0.5h, T= 37 °C Nonaka, Gen-Ichiro; Nishioka, Itsuo; Nagasawa, Tetsuro; Oura, Hikokichi; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 10; (1981); p. 2862 - 2870 View in Reaxys

O HO

OH HO

HO OH

O HO

OH HO

Rx-ID: 3701816 View in Reaxys 225/274 Yield

Conditions & References With water, tannase Ozawa, Tetsuo; Odaira, Yoshitaka; Imagawa, Hiroshi; Takino, Yoshinori; Agricultural and Biological Chemistry; vol. 44; nb. 3; (1980); p. 581 - 588 View in Reaxys

OH OH

OH HO

OH O

aqueous KOH-solution

OH HO

HO OH

Rx-ID: 5488013 View in Reaxys 226/274 Yield

Conditions & References T= 150 °C , Ausschluss von Sauerstoff Mayer; Bauni; Justus Liebigs Annalen der Chemie; vol. 611; (1958); p. 264,267 View in Reaxys

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HO O HO

O O

4.5.6.4'.5.'6'-hexahydroxy-diphenic acid-dilactone

HO O

OHO

Rx-ID: 8251061 View in Reaxys 227/274 Yield

Conditions & References Hydrolysis Reichel; Ulsperger; Naturwissenschaften; vol. 27; (1939); p. 628 View in Reaxys OH O

tannin-substance

OH HO OH

Rx-ID: 7254300 View in Reaxys 228/274 Yield

Conditions & References With sodium hydroxide Nasarenko; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 10; (1937); p. 166; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 3155 View in Reaxys Schwyzer; ; vol. 74; (1929); p. 1334,1337 View in Reaxys OH

potassium dicarbonate

OH HO OH

OH O HO

Rx-ID: 5811123 View in Reaxys 229/274 Yield

Conditions & References Widmer; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. <A> 140; (1929); p. 175 View in Reaxys OH O

tannin of Rhus coriaria

OH HO OH

Rx-ID: 7254299 View in Reaxys 230/274 Yield

Conditions & References With tannase-substance Muenz; ; (1929); p. 506,509 View in Reaxys OH O

acertannin

OH HO OH

Rx-ID: 7254295 View in Reaxys 231/274 Yield

Conditions & References With sulfuric acid, Hydrolysis

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Perkin; Uyeda; Journal of the Chemical Society; vol. 121; (1922); p. 69 View in Reaxys OH

O O

O OH

HO O

Rx-ID: 7047358 View in Reaxys 232/274 Yield

Conditions & References T= 20 °C Fischer,E.; Bergmann; Chemische Berichte; vol. 52; (1919); p. 839,840 View in Reaxys OH

O O H

OH HO

Rx-ID: 7047359 View in Reaxys 233/274 Yield

Conditions & References Fischer,E.; Bergmann; Lipschitz; Chemische Berichte; vol. 51; (1918); p. 58 View in Reaxys O HO

OH OH

N H

OH HO

NH 2 O

Rx-ID: 8259226 View in Reaxys 234/274 Yield

Conditions & References Nierenstein; Biochemical Journal; vol. 9; (1915); p. 243 View in Reaxys OH OH OH

O+

Cl –

alkali

OH H

HO OH

Rx-ID: 8469964 View in Reaxys 235/274 Yield

Conditions & References Willstaetter; Mieg; Justus Liebigs Annalen der Chemie; vol. 408; (1915); p. 61,62 View in Reaxys Willstaetter; Chem. Zentralbl.; vol. 85; nb. II; (1914); p. 1357 View in Reaxys

Rx-ID: 7544445 View in Reaxys 236/274 Yield

Conditions & References Windaus; Chem. Zentralbl.; vol. 82; nb. I; (1911); p. 1638

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View in Reaxys Windaus; Chem. Zentralbl.; vol. 85; nb. II; (1914); p. 1455 View in Reaxys OH O O

NH 2

Rx-ID: 7987725 View in Reaxys 237/274 Yield

Conditions & References im Rohr, galloyl-l-leucine Nierenstein; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 92; (1914); p. 53 View in Reaxys

OH O

O O

OH O

H 2N 2

Rx-ID: 5684009 View in Reaxys 238/274 Yield

Conditions & References Fischer,E.; Freudenberg; Chemische Berichte; vol. 46; (1913); p. 1121 View in Reaxys O

HO OH

HO O

Rx-ID: 537152 View in Reaxys 239/274 Yield

Conditions & References Richter; ; vol. 9; (1912); p. 106; Chem. Zentralbl.; vol. 84; nb. I; (1913); p. 1820 View in Reaxys HO

OH OH

O O

OH HO

O O

S OO

OH O

O HO

O O

HO HO

Rx-ID: 5673929 View in Reaxys 240/274 Yield

Conditions & References Nierenstein; Chemische Berichte; vol. 44; (1911); p. 839 View in Reaxys HO

HO OH HO

S OO

HO O HO

Rx-ID: 7254293 View in Reaxys 241/274

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Yield

Conditions & References Hydrolysis Nierenstein; Journal of the American Chemical Society; vol. 43; (1910); p. 630 View in Reaxys OH O

O O

O OH

O O

HO OH

Rx-ID: 61235 View in Reaxys 242/274 Yield

Conditions & References T= 20 °C Fischer,E.; Chemische Berichte; vol. 41; (1908); p. 2872; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 314 View in Reaxys OH

O N

O HO

O O

OH HO

HO OH

Rx-ID: 510466 View in Reaxys 243/274 Yield

Conditions & References Fischer,E.; Chemische Berichte; vol. 41; (1908); p. 2872; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 314 View in Reaxys O

OH HO

O O

S OO

O O

OH O

Rx-ID: 5488010 View in Reaxys 244/274 Yield

Conditions & References Nierenstein; Chemische Berichte; vol. 41; (1908); p. 3018 View in Reaxys OH O

O O

O OH

O O

HO OH

Rx-ID: 7987721 View in Reaxys 245/274 Yield

Conditions & References T= 20 °C Fischer,E.; Chemische Berichte; vol. 41; (1908); p. 2872; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 314 View in Reaxys OH O

O O O

O O

N H

O OH HO OH

O O

Rx-ID: 7987722 View in Reaxys 246/274

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Yield

Conditions & References T= 22 °C Fischer,E.; Chemische Berichte; vol. 41; (1908); p. 2872; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 314 View in Reaxys OH O

O O

natrium carbonate

O O

HO OH

Rx-ID: 7987723 View in Reaxys 247/274 Yield

Conditions & References T= 20 - 25 °C Fischer,E.; Chemische Berichte; vol. 41; (1908); p. 2872; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 314 View in Reaxys Br

O OH

HO Br

Rx-ID: 356482 View in Reaxys 248/274 Yield

Conditions & References With barium dihydroxide, water, T= 175 °C , im Kupferkessel Patent; Bayer and Co.; DE249939; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 10; p. 1330 View in Reaxys With potassium hydroxide, copper(I) sulfate, water, copper(II) sulfate, T= 150 °C Patent; Boehringer and Soehne; DE269544; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 190 View in Reaxys Comanducci; Marcello; Gazzetta Chimica Italiana; vol. 33 I; (1903); p. 69 View in Reaxys Br

-2

(v1)

OH HO

(v1)

O O Cu 2+ S O O

KOH-solution

OH HO

Rx-ID: 7544447 View in Reaxys 249/274 Yield

Conditions & References T= 150 °C Patent; Boehringer and Soehne; DE269544; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 190 View in Reaxys Comanducci; Marcello; Gazzetta Chimica Italiana; vol. 33 I; (1903); p. 69 View in Reaxys Br

O OH HO

KO H

O OH HO

Rx-ID: 7544448 View in Reaxys 250/274 Yield

Conditions & References Comanducci; Marcello; Gazzetta Chimica Italiana; vol. 33 I; (1903); p. 69 View in Reaxys

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OH O

O OH

OH HO

HO OH

Rx-ID: 22030235 View in Reaxys 251/274 Yield

Conditions & References Reaction Steps: 2 1: acetic acid; bromine 2: potassium hydroxide; water; copper sulfate / 150 °C With potassium hydroxide, copper(I) sulfate, water, bromine, copper(II) sulfate, acetic acid Comanducci; Marcello; Gazzetta Chimica Italiana; vol. 33 I; (1903); p. 69 View in Reaxys

O O

O OH

HO OH

Rx-ID: 5809986 View in Reaxys 252/274 Yield

Conditions & References Heffter; Chemische Berichte; vol. 34; (1901); p. 3014 View in Reaxys

O NH 2

O OH

HO OH

Rx-ID: 22213920 View in Reaxys 253/274 Yield

Conditions & References Reaction Steps: 2 1: KMnO4 2: hydriodic acid With potassium permanganate, hydrogen iodide Heffter; Chemische Berichte; vol. 34; (1901); p. 3014 View in Reaxys

OH HO O

O I

Rx-ID: 7920547 View in Reaxys 254/274 Yield

Conditions & References T= 127 °C Vogl; Monatshefte fuer Chemie; vol. 20; (1899); p. 398 View in Reaxys OH

O OH

HO HO

Rx-ID: 288850 View in Reaxys 255/274 Yield

Conditions & References With potassium hydroxide, beim Schmelzen

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Rosauer; Monatshefte fuer Chemie; vol. 19; (1898); p. 558 View in Reaxys OH O

2-oxy-3,4,5-trimethoxy-benzoic acid

OH HO OH

Rx-ID: 7254294 View in Reaxys 256/274 Yield

Conditions & References With hydrogen iodide Hamburg; Monatshefte fuer Chemie; vol. 19; (1898); p. 607 View in Reaxys OH

potassium hydroxide

OH HO

Rx-ID: 7254298 View in Reaxys 257/274 Yield

Conditions & References Rosauer; Monatshefte fuer Chemie; vol. 19; (1898); p. 558 View in Reaxys

OH O OH O

Rx-ID: 22127137 View in Reaxys 258/274 Yield

Conditions & References Reaction Steps: 2 1: hydriodic acid / 127 °C 2: KOH / beim Schmelzen With potassium hydroxide, hydrogen iodide Rosauer; Monatshefte fuer Chemie; vol. 19; (1898); p. 558 View in Reaxys OH OH

OH O

potash

OH HO

OH OH

HO OH

Rx-ID: 5488014 View in Reaxys 259/274 Yield

Conditions & References beim Schmelzen Perkin; Hummel; Journal of the Chemical Society; vol. 69; (1896); p. 1291 View in Reaxys OH

OH O

OH HO

S OO

HO OH

Rx-ID: 7987726 View in Reaxys 260/274

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Yield

Conditions & References Graebe; Eichengruen; Justus Liebigs Annalen der Chemie; vol. 269; (1892); p. 319 View in Reaxys

O O HO

O I

phosphorus

OH HO

Rx-ID: 5488011 View in Reaxys 261/274 Yield

Conditions & References T= 140 °C , im Einschlussrohr Semmler; Chemische Berichte; vol. 24; (1891); p. 3819 View in Reaxys

O O

HO O

O I

phosphorus

OH HO

Rx-ID: 5488012 View in Reaxys 262/274 Yield

Conditions & References T= 160 °C , im Rohr Roser; Justus Liebigs Annalen der Chemie; vol. 254; (1889); p. 341 View in Reaxys OH O

cotarnic acid

OH HO OH

Rx-ID: 7254296 View in Reaxys 263/274 Yield

Conditions & References With phosphorus, hydrogen iodide, T= 160 °C Roser; Justus Liebigs Annalen der Chemie; vol. 254; (1889); p. 341 View in Reaxys I

O OH

OH HO

Rx-ID: 335644 View in Reaxys 264/274 Yield

Conditions & References With potassium hydroxide, beim Schmelzen Barth; Senhofer; Chemische Berichte; vol. 8; (1875); p. 1484 Anm. View in Reaxys Br

O OH

OH HO

Rx-ID: 352784 View in Reaxys 265/274 Yield

Conditions & References With potassium hydroxide, beim Schmelzen Barth; Senhofer; Chemische Berichte; vol. 8; (1875); p. 1484 Anm.

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View in Reaxys Barth; Justus Liebigs Annalen der Chemie; vol. 142; (1867); p. 246; ; (1867); p. 275 View in Reaxys bei der Kalischmelze Barth; Senhofer; Chemische Berichte; vol. 8; (1875); p. 1484 Anm. View in Reaxys Barth; Justus Liebigs Annalen der Chemie; vol. 142; (1867); p. 246; ; (1867); p. 275 View in Reaxys I

potash

HO I

Rx-ID: 7254297 View in Reaxys 266/274 Yield

Conditions & References beim Schmelzen Barth; Chemische Berichte; vol. 8; (1875); p. 1484 Anm. View in Reaxys OH

Br HO

HO OH

Rx-ID: 352741 View in Reaxys 267/274 Yield

Conditions & References With potassium hydroxide, beim Schmelzen Barth; Senhofer; Justus Liebigs Annalen der Chemie; vol. 164; (1872); p. 118 View in Reaxys OH

potash

HO OH

Rx-ID: 7544449 View in Reaxys 268/274 Yield

Conditions & References beim Schmelzen Barth; Senhofer; Justus Liebigs Annalen der Chemie; vol. 164; (1872); p. 118 View in Reaxys OH

OH O

OH OH

Rx-ID: 22042356 View in Reaxys 269/274 Yield

Conditions & References Reaction Steps: 2 1: water; bromine water 2: KOH / beim Schmelzen With potassium hydroxide, water, bromine Barth; Senhofer; Justus Liebigs Annalen der Chemie; vol. 164; (1872); p. 118 View in Reaxys

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OH O

potassium silver cyanide

OH HO

HO Br

Rx-ID: 7987724 View in Reaxys 270/274 Yield

Conditions & References Priwoznik; Chemische Berichte; vol. 3; (1870); p. 644 View in Reaxys OH

H 2N

H O

HO OH

Rx-ID: 7915932 View in Reaxys 271/274 Yield

Conditions & References Knop,A.; Knop,W.; Journal fuer Praktische Chemie (Leipzig); vol. <1> 56; (1852); p. 329; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1852); p. 479 View in Reaxys OH

H 2N

concentrated KOH-solution

HO OH

Rx-ID: 7915933 View in Reaxys 272/274 Yield

H 2N

tannin

OH O

Rx-ID: 7433420 View in Reaxys 273/274 Yield

Conditions & References With ammonium hydroxide, sodium hydrogensulfite, T= 50 °C Fierz-David,H. E.; Blangey,L.; View in Reaxys With ammonia, sodium hydrogensulfite, T= 50 °C Fierz-David,H. E.; Blangey,L.; View in Reaxys Br

O OH

barium hydroxide

HO Br

Rx-ID: 7544446 View in Reaxys 274/274 Yield

Conditions & References T= 175 °C , im Kupferkessel Patent; Bayer and Co.; DE249939; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 10; p. 1330 View in Reaxys

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