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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)

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About This Item

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

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

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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)

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
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Angelika S Rambold et al.
Journal of neurochemistry, 107(1), 218-229 (2008-08-12)
A hallmark in prion diseases is the conformational transition of the cellular prion protein (PrP(C)) into a pathogenic conformation, designated scrapie prion protein (PrP(Sc)), which is the essential constituent of infectious prions. Here, we show that epigallocatechin gallate (EGCG) and
Y Sugita-Konishi et al.
Biochimica et biophysica acta, 1472(1-2), 42-50 (1999-11-26)
We studied the effects of six catechin derivatives (catechin, epigallocatechin, epicatechin, epicatechin gallate, epigallocatechin gallate (EGCg) and gallocatechin gallate (GCg)) in green tea on the production and extracellular release of Vero toxins (VTs) from enterohemorrhagic Escherichia coli (EHEC) cultured at
Sang Min Lee et al.
Lipids, 43(5), 419-429 (2008-03-28)
The (-)-gallocatechin gallate (GCG) concentration in some tea beverages can account for as much as 50% of the total catechins, as a result of sterilization. The present study aims to examine the effects of GCG-rich tea catechins on hyperlipidemic rats
Fan Jiang et al.
Clinical immunology (Orlando, Fla.), 137(3), 347-356 (2010-09-14)
Four catechins with the galloyl moiety, including catechin gallate (CG), epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), and epicatechin gallate (ECG), were found to inhibit HIV-1 integrase effectively as determined by our ELISA method. In our docking study, it is proposed
Ikuo Ikeda et al.
Journal of agricultural and food chemistry, 51(25), 7303-7307 (2003-12-04)
It has been known that tea catechins, (-)-epicatechin (1), (-)-epigallocatechin (2), (-)-epicatechin gallate (3), and (-)-epigallocatechin gallate (4) are epimerized to(-)-catechin (5), (-)-gallocatechin (6), (-)-catechin gallate (7), and (-)-gallocatechin gallate (8), respectively, during retort pasteurization. We previously reported that tea
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