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
• NACRES: NA.77
• PubChem Substance ID: 24895275
• UNSPSC Code: 12352200
• MDL number: MFCD00214298

Properties

• biological source: green tea
• Quality Level: 200
• 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.[1] 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.[2]

Application

(−)-Gallocatechin gallate has been used:

• to perform the tannase activity assay of the recombinant Lactobacillus plantarum tannase enzyme[3]
• to study its inhibitory effects on HIV-1 integrase activity [1]
• to study its regulatory mechanism on cholesterol metabolism in rat liver[4]
• to analyze its effect as a polyphenol on human spermatozoa and their application in assisted reproductive technology[5]
• to study the interference in stress protective activity of cellular prion protein (PrP^C) and the formation of scrapie prion protein (PrP^Sc)[6]

Biochem/physiol Actions

Tea catechins like (−)-Gallocatechin gallate are known to have antiviral, antioxidative, antimutagenic and antiobesity activities.[2] 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.[1] GCG also shows impeding effect on the release of vero toxins (VTs) by enterohemorrhagic Escherichia coli.[7] 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.[2]

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: 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: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves