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G6782

Sigma-Aldrich

(−)-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:
Molecular Weight:
458.37
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

green tea

Quality Level

assay

≥98% (HPLC)

form

powder

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

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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 (PrPC) and the formation of scrapie prion protein (PrPSc)

Packaging

5 mg in glass bottle

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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