G6782

(−)-Gallocatechin gallate

from green tea, ≥98% (HPLC)

• Synonym(s): (2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)
• Empirical Formula (Hill Notation): C₂₂H₁₈O₁₁
• CAS Number: 4233-96-9
• Molecular Weight: 458.37
• MDL number: MFCD00214298
• UNSPSC Code: 12352200
• PubChem Substance ID: 24895275
• NACRES: NA.77

Properties

• biological source: green tea
• Assay: ≥98% (HPLC)
• form: powder
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@@H](Oc2c1)c4cc(O)c(O)c(O)c4
• InChI: 1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21+/m1/s1
• InChI key: WMBWREPUVVBILR-NQIIRXRSSA-N

Description

General description

(−)-Gallocatechin gallate is a polyphenolic compound having a galloyl moiety. It is an epimerized form of epigallocatechin gallate, which is common tea catechin. Epimerization of tea catechins is common upon heat treatment or pasteurization process.

Application

(−)-Gallocatechin gallate has been used:

• to perform the tannase activity assay of the recombinant Lactobacillus plantarum tannase enzyme
• to study its inhibitory effects on HIV-1 integrase activity
• to study its regulatory mechanism on cholesterol metabolism in rat liver
• to analyze its effect as a polyphenol on human spermatozoa and their application in assisted reproductive technology
• to study the interference in stress protective activity of cellular prion protein (PrP^C) and the formation of scrapie prion protein (PrP^Sc)

Biochem/physiol Actions

Tea catechins like (−)-Gallocatechin gallate are known to have antiviral, antioxidative, antimutagenic and antiobesity activities. It exhibits human immunodeficiency virus-1 (HIV-1) integrase inhibitory activity by disturbing the interaction between the human immunodeficiency virus-1 (HIV-1) integrase and virus DNA. GCG also shows impeding effect on the release of vero toxins (VTs) by enterohemorrhagic Escherichia coli. It displays an inhibitory effect on cholesterol absorption and is reported to be more effective than tea catechins in lowering plasma cholesterol, thus preventing atherosclerosis.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves