970-73-0

Basic information

• Product Name: (+)-GALLOCATECHIN
• Synonyms: (+)-GALLOCATECHIN;2α-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3β,5,7-triol;(2S)-2β-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3α,5,7-triol;(2S)-3,4-Dihydro-2β-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3α,5,7-triol;(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol;2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-, (2R-trans-);Nsc674038;(2R,3S)-2-(3,4,5-trihydroxyphenyl)chroman-3,5,7-triol
• CAS NO: 970-73-0
• Molecular Formula: C₁₅H₁₄O₇
• Molecular Weight: 306.27
• Product Categories: Flavonoids
• Mol File: 970-73-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: 218 °C(Solv: water (7732-18-5))
• Boiling Point: 685.6 °C at 760 mmHg
• Flash Point: 368.5 °C
• Appearance: /
• Density: 1.695 g/cm³
• Storage Temp.: 2-8°C
• Solubility: H2O: 5?mg/mL with brief sonication
• PKA: 9.02±0.15(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (+)-GALLOCATECHIN(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-GALLOCATECHIN(970-73-0)
• EPA Substance Registry System: (+)-GALLOCATECHIN(970-73-0)

Safety Data

• Hazard Codes: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 970-73-0(Hazardous Substances Data)

Usage

Description

(+)-Gallocatechin is a polyphenol and flavonoid that has been isolated from the leaves of tea plants and has diverse biological activities. It inhibits the adherence of P. gingivalis onto human buccal epithelial cells by more than 50% when used at a concentration of 250 μg/ml. (+)-Gallocatechin has antimutagenic properties in UV-irradiated E. coli cells. It inhibits cell death induced by D-galactosamine and TNF-α in primary cultured mouse hepatocytes by 29.9% when used at a concentration of 80 μM. (+)-Gallocatechin (100 μM) inhibits HCT116 colorectal cancer cell proliferation by 57%.

Uses

(+)-Gallocatechin is antioxidant isomer of (-)-Gallocatechin (G188990), a potential cancer chemopreventive agent that inhibits the growth and adherence of P. gingivalis onto the buccal epithelial cells. An epimer of (-)-Epigallocatechin (E588940).

Definition

ChEBI: A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.

Chemical Properties

Off-White Solid

Upstream product

• 332386-74-0 (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol 
• 1449477-34-2 C₂₄H₃₆O₉ 
• 1449477-27-3 C₂₄H₃₄O₈ 
• 1449477-26-2 C₄₄H₅₀O₁₀ 
• 1449477-38-6 C₄₄H₄₈O₁₀ 
• 1449477-36-4 C₄₄H₅₀O₁₀ 
• 1449477-39-7 C₃₀H₃₈O₁₀ 
• 148802-38-4 catechin-(4α->8)-gallocatechin-(4α->6)-gallocatechin 
• 100-53-8 phenylmethanethiol 
• 135820-76-7 gallocatechin-(4α->8)-gallocatechin-(4α->8)-epigallocatechin 
• 1449477-37-5 C₃₀H₃₈O₁₀ 
• 108-73-6 3,5-dihydroxyphenol 
• 1359849-47-0 epigallocatechin-3-O-p-hydroxybenzoate-(4β->8)-epigallocatechin 
• 1333874-50-2 7-O-(β-Glcp-6-O-galloyl)-(+)-catechin-(4α->8)-(+)-catechin-(4α->8)-(-)-epigallocatechin 

Downstream Products

• 145826-25-1 eugenigranidin A 
• 1236228-58-2 theasinensin C 
• 143883-96-9 4,5,6,2',3',4'-Hexahydroxy-6'-((2R,3R)-3,5,7-trihydroxy-chroman-2-yl)-biphenyl-2-carboxylic acid (1R,2R,3R,5S)-5-carboxy-2,3,5-trihydroxy-cyclohexyl ester 
• 21731-10-2 5-((2R,3R)-3,5,7-triacetoxychroman-2-yl)benzene-1 ,2,3-triyl triacetate 
• 273931-30-9 (2R,3S)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-ol 
• 569-77-7 purpurogallin 
• 102208-15-1 theaflagallin 
• 17291-05-3 4'-O-methylepigallocatechin 
• 4670-05-7 theaflavin 
• 302776-47-2 theanaphthoquinone 

Relevant articles and documents

Study on in Vitro Preparation and Taste Properties of N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols

N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) were prepared by an in vitro model reaction, and the taste thresholds of EPSFs and their dose-over-threshold factors in large-leaf yellow tea (LYT) were investigated. The effects of initial reactant

Metabolic characterization of the anthocyanidin reductase pathway involved in the biosynthesis of flavan-3-ols in elite Shuchazao tea (Camellia sinensis) cultivar in the field

Anthocyanidin reductase (ANR) is a key enzyme in the ANR biosynthetic pathway of flavan-3-ols and proanthocyanidins (PAs) in plants. Herein, we report characterization of the ANR pathway of flavan-3-ols in Shuchazao tea (Camellia sinesis), which is an elite and widely grown cultivar in China and is rich in flavan-3-ols providing with high nutritional value to human health. In our study, metabolic profiling was preformed to identify two conjugates and four aglycones of flavan-3-ols: (-)-epigallocatechin-gallate [(-)-EGCG], (-)-epicatechin-gallate [(-)-ECG], (-)-epigallocatechin [(-)-EGC], (-)-epicatechin [(-)-EC], (+)-catechin [(+)-Ca], and (+)-gallocatechin [(+)-GC], of which (-)-EGCG, (-)-ECG, (-)-EGC, and (-)-EC accounted for 70-85% of total flavan-3-ols in different tissues. Crude ANR enzyme was extracted from young leaves. Enzymatic assays showed that crude ANR extracts catalyzed cyanidin and delphinidin to (-)-EC and (-)-Ca and (-)-EGC and (-)-GC, respectively, in which (-)-EC and (-)-EGC were major products. Moreover, two ANR cDNAs were cloned from leaves, namely CssANRa and CssANRb. His-Tag fused recombinant CssANRa and CssANRb converted cyanidin and delphinidin to (-)-EC and (-)-Ca and (-)-EGC and (-)-GC, respectively. In addition, (+)-EC was observed from the catalysis of recombinant CssANRa and CssANRb. Further overexpression of the two genes in tobacco led to the formation of PAs in flowers and the reduction of anthocyanins. Taken together, these data indicate that the majority of leaf flavan-3-ols in Shuchazao's leaves were produced from the ANR pathway.

Isolation of two new bioactive proanthocyanidins from Cistus salvifolius herb extract

Two new proanthocyanidins, epigallocatechin-3-O-p-hydroxybenzoate- (4β→8)-epigallocatechin (1) and epigallocatechin-3-O-p- hydroxybenzoate-(4β→8)-epigallocatechin-3-O-gallate (2) in addition to the known compound epigallocatechin-(4β→6)-epigallocatechin-3-O- gallate (3), were isolated from the air-dried herb of Cistus salvifolius. The chemical structures were determined on the basis of 1D-and 2D-NMR-spectra (HSQC, HMBC) of their peracetylated derivatives, MALDI-TOF-mass spectra, and by acid-catalysed degradation with phloroglucinol. The isolated compounds 1-3 and the water extract of C. salvifolius herb were tested for their inhibitory activities against COX-1 and COX-2. Compound 2 showed the strongest inhibitory effect on COX-2 followed by compound 3, compound 1 and the water extract, while compounds 1-3 exhibited moderate in vitro inhibition against COX-1.