EPIGALLOCATECHIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H14O7
Molecular Weight	306.2675
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C3=CC(O)=C(O)C(O)=C3

InChI

InChIKey=XMOCLSLCDHWDHP-IUODEOHRSA-N

InChI=1S/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

HIDE SMILES / InChI

Molecular Formula	C15H14O7
Molecular Weight	306.2675
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12925310

(-)-Epigallocatechin is a polyphenol, which occurs naturally in various plants, including green tea leaves. The compound was shown to have anti-cancer activity in vitro, with breast cancer, lung cancer, and colon cancer cells. The commercial preparation of Polyphenon E contains about 3% (-)-epigallocatechin as an impurity.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12925310	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Determination of tea components with antioxidant activity.	2003-07-16	12848521
Complex effects of different green tea catechins on human platelets.	2003-07-10	12832052
Hop (Humulus lupulus L.) proanthocyanidins characterized by mass spectrometry, acid catalysis, and gel permeation chromatography.	2003-07-02	12822954
Inhibition of metalloproteinase-9 activity and gene expression by polyphenolic compounds isolated from the bark of Tristaniopsis calobuxus (Myrtaceae).	2003-07	12943230
Identification of potential aryl hydrocarbon receptor antagonists in green tea.	2003-07	12870889
Chain-breaking antioxidant activity of natural polyphenols as determined during the chain oxidation of methyl linoleate in Triton X-100 micelles.	2003-06-15	12781778
Radical chemistry of epigallocatechin gallate and its relevance to protein damage.	2003-06-01	12745262
Antitumor principle constituents of Myrica rubra Var. acuminata.	2003-05-07	12720379
Microemulsion electrokinetic chromatography for the analysis of green tea catechins: effect of the cosurfactant on the separation selectivity.	2003-05	12761797
Enzymology of methylation of tea catechins and inhibition of catechol-O-methyltransferase by (-)-epigallocatechin gallate.	2003-05	12695345
The specificities of protein kinase inhibitors: an update.	2003-04-01	12534346
Inhibition of adenovirus infection and adenain by green tea catechins.	2003-04	12742577
DNA degradation by water extract of green tea in the presence of copper ions: implications for anticancer properties.	2003-04	12722140
Glucuronides of tea catechins: enzymology of biosynthesis and biological activities.	2003-04	12642472
MALDI-TOF mass spectrometry and PSD fragmentation as means for the analysis of condensed tannins in plant leaves and needles.	2003-04	12591272
Factors affecting the levels of tea polyphenols and caffeine in tea leaves.	2003-03-26	12643643
Determination of tea polyphenols and caffeine in tea flowers (Camellia sinensis) and their hydroxyl radical scavenging and nitric oxide suppressing effects.	2003-02-12	12568558
Antioxidative compounds from Crotalaria sessiliflora.	2003-02	12729010
Green tea catechins evoke a phasic contraction in rat aorta via H2O2-mediated multiple-signalling pathways.	2003-01-25	12542460
Epimerization of tea catechins and O-methylated derivatives of (-)-epigallocatechin-3-O-gallate: relationship between epimerization and chemical structure.	2003-01-15	12517118
Polymeric proanthocyanidins from the bark of Hamamelis virginiana.	2003-01	12567291
Green tea catechins inhibit the cultured smooth muscle cell invasion through the basement barrier.	2003-01	12482547
Suppression of fatty acid synthase in MCF-7 breast cancer cells by tea and tea polyphenols: a possible mechanism for their hypolipidemic effects.	2003	12931129
Inhibition of proliferation of human cancer cells and cyclooxygenase enzymes by anthocyanidins and catechins.	2003	12925310
Analysis of oxidized epigallocatechin gallate by liquid chromatography/mass spectrometry.	2003	12876693
Topoisomerase I and II enzyme inhibitory aqueous extract of Ardisia compressa and ardisin protect against benomyl oxidation of hepatocytes.	2002-12-18	12475294
(-)-Epigallocatechin (EGC) of green tea induces apoptosis of human breast cancer cells but not of their normal counterparts.	2002-12	12462380
Antioxidant effects of green tea polyphenols on free radical initiated peroxidation of rat liver microsomes.	2002-12	12426080
Direct scavenging of nitric oxide and superoxide by green tea.	2002-12	12419687
Tea enhances insulin activity.	2002-11-20	12428980
Green tea polyphenols inhibit metalloproteinase activities in the skin, muscle, and blood of rainbow trout.	2002-11-20	12428978
Effects of external factors on the interaction of tea catechins with lipid bilayers.	2002-11	12506968
Accumulation of epigallocatechin quinone dimers during tea fermentation and formation of theasinensins.	2002-11	12444680
Contribution of presystemic hepatic extraction to the low oral bioavailability of green tea catechins in rats.	2002-11	12386131
Regulation of IGFBP-5 expression during tumourigenesis and differentiation of oral keratinocytes.	2002-11	12375264
Effects of catechins on vascular tone in rat thoracic aorta with endothelium.	2002-10-11	12270760
Opportunities for nutritional amelioration of radiation-induced cellular damage.	2002-10	12361786
Varietal differences among the polyphenol profiles of seven table grape cultivars studied by LC-DAD-MS-MS.	2002-09-25	12236700
Prevention of nitric oxide-mediated 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Parkinson's disease in mice by tea phenolic epigallocatechin 3-gallate.	2002-09	12387363
Activity-guided fractionation of green tea extract with antiproliferative activity against human stomach cancer cells.	2002-09	12230128
Urinary tea polyphenols in relation to gastric and esophageal cancers: a prospective study of men in Shanghai, China.	2002-09	12189193
Involvement of protein kinase C activation and cell survival/ cell cycle genes in green tea polyphenol (-)-epigallocatechin 3-gallate neuroprotective action.	2002-08-23	12058035
Effect of tea catechins on cellular lipid peroxidation and cytotoxicity in HepG2 cells.	2002-07	12224642
Inhibition of aromatase activity by green tea extract catechins and their endocrinological effects of oral administration in rats.	2002-07	12065214
Inhibition of the PDGF beta-receptor tyrosine phosphorylation and its downstream intracellular signal transduction pathway in rat and human vascular smooth muscle cells by different catechins.	2002-06	12039871
Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2).	2002-05-20	12085217
Effects of epigallocatechin 3-O-gallate on cellular antioxidative system in HepG2 cells.	2002-04	12171441
Inhibition of BMP-induced ectopic bone formation by an antiangiogenic agent (epigallocatechin 3-gallate).	2002	12489208
[Study on the analytical methods of catechins in tea and green tea polyphenol samples by high performance liquid chromatography].	2001-09	12545432
Green tea catechins and vitamin E inhibit angiogenesis of human microvascular endothelial cells through suppression of IL-8 production.	2001	12094614

Patents

Sample Use Guides

In Vivo Use Guide

In a clinical trial, patients were given 1, 2, 3 or 4 capsules (1 capsule contains 37 mg (-)-epigallocatechin).

Route of Administration: Oral

In Vitro Use Guide

In a cell growth assay, human tumor cell lines MCF-7, SF-268, HCT-116 and NCI-H460 were treated with 100, 50, 25, 12.5, and 6.25 uM of (-)-epigallocatechin for 48 h. At concentration of 50 uM, the drug gave 50%, 10%, 60% and 40% inhibition of growth of breast, CNS, colon, and lung cancer cells, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:32:52 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:52 GMT 2025`
Record UNII	7Z197MG6QL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SUNPHENON EGC

Preferred Name

English

EPIGALLOCATECHIN

Common Name

English

EGC

Common Name

English

(-)-EPIGALLOCATECHOL

Common Name

English

EPIGALLOCATECHOL

Common Name

English

2H-1-BENZOPYRAN-3,5,7-TRIOL, 3,4-DIHYDRO-2-(3,4,5-TRIHYDROXYPHENYL)-, (2R,3R)-

Systematic Name

English

GALLOEPICATECHIN

Common Name

English

(-)-EPI-GALLOCATECHIN

Common Name

English

(-)-EPIGALLOCATECHIN

Common Name

English

NSC-674039

Code

English

EPI-GALLOCATECHIN

Common Name

English

L-EPIGALLOCATECHIN

Common Name

English

ANTISCURVY FACTOR C2

Common Name

English

3,3',4',5,5',7-FLAVANHEXOL

Systematic Name

English

(-)-EPIGALLOCATECHIN(EGC) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C63651