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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14O7
Molecular Weight 306.268
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPIGALLOCATECHIN

SMILES

c1c(cc(c(c1O)O)O)[C@]2([H])[C@@]([H])(Cc3c(cc(cc3O2)O)O)O

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 306.268
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

(-)-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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Biological evaluation of proanthocyanidin dimers and related polyphenols.
1999 Jul
Green tea catechins and vitamin E inhibit angiogenesis of human microvascular endothelial cells through suppression of IL-8 production.
2001
Differential responses of skin cancer-chemopreventive agents silibinin, quercetin, and epigallocatechin 3-gallate on mitogenic signaling and cell cycle regulators in human epidermoid carcinoma A431 cells.
2001
Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid.
2001 Apr
Plasma concentrations of individual tea catechins after a single oral dose in humans.
2001 Dec
Phase I pharmacokinetic study of tea polyphenols following single-dose administration of epigallocatechin gallate and polyphenon E.
2001 Jan
Degradation of green tea catechins in tea drinks.
2001 Jan
Induction of apoptosis by green tea catechins in human prostate cancer DU145 cells.
2001 Jan 26
Simultaneous determination of twelve tea catechins by high-performance liquid chromatography with electrochemical detection.
2001 Jun
Analysis of urinary metabolites of tea catechins by liquid chromatography/electrospray ionization mass spectrometry.
2001 Jun
Green tea polyphenol epigallocatechin inhibits DNA replication and consequently induces leukemia cell apoptosis.
2001 Jun
Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase.
2001 Jun 1
Cutaneous photoprotection from ultraviolet injury by green tea polyphenols.
2001 Mar
Antimutagenic activity of green tea and black tea extracts studied in a dynamic in vitro gastrointestinal model.
2001 Mar 1
Stereospecificity in membrane effects of catechins.
2001 Mar 14
Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes.
2001 May
A tea catechin suppresses the expression of the high-affinity IgE receptor Fc epsilon RI in human basophilic KU812 cells.
2001 May
Composition of grape skin proanthocyanidins at different stages of berry development.
2001 Nov
Effects of purified green and black tea polyphenols on cyclooxygenase- and lipoxygenase-dependent metabolism of arachidonic acid in human colon mucosa and colon tumor tissues.
2001 Nov 1
[Study on the analytical methods of catechins in tea and green tea polyphenol samples by high performance liquid chromatography].
2001 Sep
Effects of epigallocatechin 3-O-gallate on cellular antioxidative system in HepG2 cells.
2002 Apr
Antitumor activity of compounds isolated from leaves of Eriobotrya japonica.
2002 Apr 10
Involvement of protein kinase C activation and cell survival/ cell cycle genes in green tea polyphenol (-)-epigallocatechin 3-gallate neuroprotective action.
2002 Aug 23
Antioxidant effects of green tea polyphenols on free radical initiated peroxidation of rat liver microsomes.
2002 Dec
Direct scavenging of nitric oxide and superoxide by green tea.
2002 Dec
Topoisomerase I and II enzyme inhibitory aqueous extract of Ardisia compressa and ardisin protect against benomyl oxidation of hepatocytes.
2002 Dec 18
Deodorizing effects of tea catechins on amines and ammonia.
2002 Feb
Enhancement of inward Ca(2+) currents in bovine chromaffin cells by green tea polyphenol extracts.
2002 Feb
Effects of dietary antioxidants on human DNA ex vivo.
2002 Jan
Isolation and characterization of alkyl peroxy radical scavenging compound from leaves of Laurus nobilis.
2002 Jan
Kinetic analysis and mechanistic aspects of autoxidation of catechins.
2002 Jan 15
Green tea polyphenols inhibit human vascular smooth muscle cell proliferation stimulated by native low-density lipoprotein.
2002 Jan 2
Green tea polyphenol (-)-epigallocatechin 3-gallate inhibits MMP-2 secretion and MT1-MMP-driven migration in glioblastoma cells.
2002 Jan 30
Effect of tea catechins on cellular lipid peroxidation and cytotoxicity in HepG2 cells.
2002 Jul
Polyphenolic antioxidants from the fruits of Chrysophyllum cainito L. (Star Apple).
2002 Mar 13
Evaluation of the antigenotoxic potential of monomeric and dimeric flavanols, and black tea polyphenols against heterocyclic amine-induced DNA damage in human lymphocytes using the Comet assay.
2002 Mar 25
Regulation of IGFBP-5 expression during tumourigenesis and differentiation of oral keratinocytes.
2002 Nov
Tea enhances insulin activity.
2002 Nov 20
Green tea polyphenols inhibit metalloproteinase activities in the skin, muscle, and blood of rainbow trout.
2002 Nov 20
Effects of catechins on vascular tone in rat thoracic aorta with endothelium.
2002 Oct 11
Suppression of fatty acid synthase in MCF-7 breast cancer cells by tea and tea polyphenols: a possible mechanism for their hypolipidemic effects.
2003
MALDI-TOF mass spectrometry and PSD fragmentation as means for the analysis of condensed tannins in plant leaves and needles.
2003 Apr
Determination of tea polyphenols and caffeine in tea flowers (Camellia sinensis) and their hydroxyl radical scavenging and nitric oxide suppressing effects.
2003 Feb 12
Green tea catechins inhibit the cultured smooth muscle cell invasion through the basement barrier.
2003 Jan
Green tea catechins evoke a phasic contraction in rat aorta via H2O2-mediated multiple-signalling pathways.
2003 Jan-Feb
Inhibition of metalloproteinase-9 activity and gene expression by polyphenolic compounds isolated from the bark of Tristaniopsis calobuxus (Myrtaceae).
2003 Jul
Identification of potential aryl hydrocarbon receptor antagonists in green tea.
2003 Jul
Hop (Humulus lupulus L.) proanthocyanidins characterized by mass spectrometry, acid catalysis, and gel permeation chromatography.
2003 Jul 2
Radical chemistry of epigallocatechin gallate and its relevance to protein damage.
2003 Jun 1
Antitumor principle constituents of Myrica rubra Var. acuminata.
2003 May 7
Patents

Sample Use Guides

In a clinical trial, patients were given 1, 2, 3 or 4 capsules (1 capsule contains 37 mg (-)-epigallocatechin).
Route of Administration: Oral
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 Sat Jun 26 00:05:08 UTC 2021
Edited
by admin
on Sat Jun 26 00:05:08 UTC 2021
Record UNII
7Z197MG6QL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
SUNPHENON EGC
Brand Name 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
Created by admin on Sat Jun 26 00:05:08 UTC 2021 , Edited by admin on Sat Jun 26 00:05:08 UTC 2021
Code System Code Type Description
DRUG BANK
DB03823
Created by admin on Sat Jun 26 00:05:08 UTC 2021 , Edited by admin on Sat Jun 26 00:05:08 UTC 2021
PRIMARY
CAS
970-74-1
Created by admin on Sat Jun 26 00:05:08 UTC 2021 , Edited by admin on Sat Jun 26 00:05:08 UTC 2021
PRIMARY
PUBCHEM
72277
Created by admin on Sat Jun 26 00:05:08 UTC 2021 , Edited by admin on Sat Jun 26 00:05:08 UTC 2021
PRIMARY
FDA UNII
7Z197MG6QL
Created by admin on Sat Jun 26 00:05:08 UTC 2021 , Edited by admin on Sat Jun 26 00:05:08 UTC 2021
PRIMARY
EVMPD
SUB77259
Created by admin on Sat Jun 26 00:05:08 UTC 2021 , Edited by admin on Sat Jun 26 00:05:08 UTC 2021
PRIMARY
NCI_THESAURUS
C68453
Created by admin on Sat Jun 26 00:05:08 UTC 2021 , Edited by admin on Sat Jun 26 00:05:08 UTC 2021
PRIMARY
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