3371-27-5

Basic information

• Product Name: (-)-GALLOCATECHIN
• Synonyms: [2S,3R]-2-[3,4,5-TRIHYDROXYPHENYL]-3,4-DIHYDRO-1[2H]-BENZOPYRAN-3,5,7-TRIOL;(-)-GALLOCATECHIN;GALLOCATECHIN;(-)-GC;GALLOCATECHIN, (-)-(SH);()-Gallocatechin,(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol;(2S,3R)-3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol;(2S-trans)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
• CAS NO: 3371-27-5
• Molecular Formula: C₁₅H₁₄O₇
• Molecular Weight: 306.27
• Product Categories: Miscellaneous Natural Products;Catechins & Tannins;Aromatics;Heterocycles;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 3371-27-5.mol
• Article Data: 28

Chemical Properties

• Melting Point: 200℃
• Boiling Point: 685.63 °C at 760 mmHg
• Flash Point: 368.456 °C
• Appearance: /
• Density: 1.696 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.776
• Storage Temp.: 2-8°C
• Solubility: H2O: 5 mg/mL with brief sonication
• PKA: 9.02±0.15(Predicted)
• CAS DataBase Reference: (-)-GALLOCATECHIN(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-GALLOCATECHIN(3371-27-5)
• EPA Substance Registry System: (-)-GALLOCATECHIN(3371-27-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3371-27-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 3371-27-5 differently. You can refer to the following data:
1. An antioxidant with free radical scavenging ability; a potential cancer chemopreventive agent. It inhibits the growth and adherence of P. gingivalis onto the buccal epithelial cells. An epimer of (-)- Epigallocatechin (E588940).
2. Polyphenolic compound from green tea. Possesses free-radical scavenging ability
3. (?)-Gallocatechin has been used as a reference standard:for the identification of phenolic compounds present in Pineapple (Ananas comosus) using high-performance liquid chromatography (HPLC)to evaluate the catechin profiles from Camellia sinensis green tea, white tea, and flower sample by high-performance liquid chromatography/photodiode array detection (RP-HPLC/PDAD) analysisas a reference standard for the flavan-3-ols profiling muscadine grape hybrid varieties using high-performance liquid chromatography-quadrupole, time-of-flight, tandem mass spectrometry (HPLC-qTOF-MS/MS) analysis

General Description

Gallocatechin belongs to the catechin class of organic compounds and is one of the major components of green tea. The beneficial effects of catechins include anti-tumorigenic, anti-mutagenic, anti-pathogenic, and anti-oxidative properties.

Biochem/physiol Actions

(?)-Gallocatechin (GC) exerts antioxidant properties by scavenging free radicals. It can also inhibit osteoclastgenesis. GC elicits antimutagenic activity in Escherichia coli against ultraviolet (UV)-induced mutation. It also displays an inhibitory effect on the growth and adherence of?Porphyromonas gingivalis?in the buccal epithelial cells.

InChI:InChI=1/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m1/s1

Upstream product

• 402492-44-8 (2R,3S,4S)-4-Phenylsulfanyl-2-(3,4,5-trihydroxy-phenyl)-chroman-3,5,7-triol 
• 1449477-34-2 C₂₄H₃₆O₉ 
• 1449477-27-3 C₂₄H₃₄O₈ 
• 1449477-26-2 C₄₄H₅₀O₁₀ 
• 1449477-38-6 C₄₄H₄₈O₁₀ 
• 1449477-36-4 C₄₄H₅₀O₁₀ 
• 1449477-39-7 C₃₀H₃₈O₁₀ 
• 60-87-7 10-[2-(dimethylamino)propyl]phenothiazine 
• 1449477-37-5 C₃₀H₃₈O₁₀ 
• 970-73-0 epigallocatechin 
• 89013-66-1 (-)-epigallocatechin 3,3'-di-O-gallate 
• 89013-67-2 (-)-epigallocatechin 3,4'-di-O-gallate 
• 13270-61-6 delphinidin 
• 989-51-5 (-)-gallocatechin 3-gallate 

Downstream Products

• 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 
• 3371-27-5 (-)-gallocatechin 
• 108-73-6 3,5-dihydroxyphenol 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 4670-05-7 theaflavin 
• 302776-47-2 theanaphthoquinone 

Relevant articles and documents

Oxidation and epimerization of epigallocatechin in banana fruits

To examine the metabolism of proanthocyanidins in banana fruit, (-)- epigallocatechin was treated with the homogenate of the fruit flesh to yield (-)-gallocatechin and an oxidation product, 1-(3,4,5-trihydroxyphenyl)-3- (2,4,6-trihydroxyphenyl)-2-hydroxy-

Enzymatic oxidation of gallocatechin and epigallocatechin: Effects of C-ring configuration on the reaction products

Tea leaf is rich in pyrogallol-type catechins, and their oxidation is important in the generation of black tea polyphenols. In the present study, the enzymatic oxidation of three pyrogallol-type catechins, (+)- and (-)-gallocatechins and (-)-epigallocatechin, was compared. The reactions yielded unstable quinone products, which were trapped as condensation products with o-phenylenediamine. The oxidation of (+)-gallocatechin proceeded very slowly compared to the reaction of (-)-epigallocatechin, and yielded a proepitheaflagallin-type dimer as the major product, though oxidation of (-)-epigallocatechin gave predominantly dehydrotheasinensin C. The cis-configuration of the C-3 hydroxyl group and the B-ring of (-)-epigallocatechin was apparently crucial for rapid and selective production of dehydrotheasinensin C. Oxidation of (-)-gallocatechin proceeded in a manner similar to that of (+)-gallocatechin, and produced an enantiomer of the (+)-gallocatechin product. The results suggest that enzymes catalyze oxidation of the pyrogallol B-ring to the o-quinone, with subsequent non-enzymatic coupling reactions proceed under highly steric control.

Mechanism of oolongtheanin formation via three intermediates

To clarify the mechanism of oolongtheanin formation, the oxidations of (?)-epigallocatechin and (?)-epigallocatechin gallate were investigated, and key intermediates were isolated. These intermediates were determined to be dehydrotheasinensins and pro-oolongtheanins, which we have reported previously, and one novel intermediate. Based on the chemical structures of these intermediates, a mechanism was proposed for oolongtheanin formation from catechins, and confirmed by NMR and GC–MS analysis.

Enantioselective total syntheses of (+)-gallocatechin, (-)- epigallocatechin, and 8-C-ascorbyl-(-)-epigallocatechin

Reading the tea leaves: The enatioselective total syntheses of 8-C-ascorbyl-(-)-epigallocatechin was accomplished by CuII-mediated oxidative coupling of ascorbic acid and (-)-epigallocatechin as a key step. Also, the asymmetric total syntheses of tea-leaf extracts (+)-gallocatechin and (-)-epigallocatechin were achieved by Au-catalyzed intramolecular cycliarylation of the precursor epoxide and Sharpless dihydroxylation. Copyright