U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H18O11
Molecular Weight 458.3717
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPIGALLOCATECHIN GALLATE

SMILES

OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C4=CC(O)=C(O)C(O)=C4)C(O)=C1

InChI

InChIKey=WMBWREPUVVBILR-WIYYLYMNSA-N
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

HIDE SMILES / InChI
Epigallocatechin-3-gallate (EGCG), the major polyphenol from green tea, has the potential to impact a variety of human diseases. EGCG functions as a powerful antioxidant, preventing oxidative damage in healthy cells, but also as an antiangiogenic and antitumor agent and as a modulator of tumor cell response to chemotherapy. It was shown, that EGCG can inhibit 5-cytosine DNA methyltransferase (DNMT) activity and reactivate methylation-silenced genes in cancer cells and another of the probable mechanisms by EGCG exercise their anti-tumor property is through the suppression of the NFκB signaling pathway. EGCG has emerged as a potential neuroprotective agent for the treatment of neurological disorders associated with harmful effects of reactive oxygen species. The neuroprotective mechanism of action is probably based on several factors, including EGCG's modulation of several signal transduction pathways, its influence on the expression of genes regulating cell survival or programmed cell death, as well as its modulation of mitochondrial function. A phase II/III trial of oral Sunphenon epigallocatechin-3-gallate in patients with progressive multiple sclerosis has been completed. In addition, EGCG was in phase III clinical trials for the treatment of multiple system atrophy and for patients with Duchenne Muscular Dystrophy ((DMD). DMD is the most frequent neuromuscular condition to occur in childhood and youth.

CNS Activity

Curator's Comment: A low concentration of epigallocatechin gallate that was suggested from BBB permeability may prevent cognitive dysfunction by increasing brain plasticity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P26358
Gene ID: 1786.0
Gene Symbol: DNMT1
Target Organism: Homo sapiens (Human)
6.89 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of the green tea derivative, EGCG, by the topical route of administration in mouse and human skin.
1999
A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review.
2000
Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense.
2000 May
Epigallocatechin gallate protects U937 cells against nitric oxide-induced cell cycle arrest and apoptosis.
2001
Inactivation of parvovirus B19 in coagulation factor concentrates by UVC radiation: assessment by an in vitro infectivity assay using CFU-E derived from peripheral blood CD34+ cells.
2001 Apr
Prolyl endopeptidase inhibitors from green tea.
2001 Aug
Tea catechin, (-)-epigallocatechin gallate, causes membrane depolarizations of myenteric neurons in the guinea-pig small intestine.
2001 Aug 24
Anticarcinogenic antioxidants as inhibitors against intracellular oxidative stress.
2001 Dec
The medicinal action of androgens and green tea epigallocatechin gallate.
2001 Dec
Effect of polyphenols on calcium content and alkaline phosphatase activity in rat femoral tissues in vitro.
2001 Dec
The green tea polyphenol (-)-epigallocatechin gallate attenuates beta-amyloid-induced neurotoxicity in cultured hippocampal neurons.
2001 Dec 21
Synthesis of (-)-[4-3H]epigallocatechin gallate and its metabolic fate in rats after intravenous administration.
2001 Feb
Green tea polyphenols as potent enhancers of glucocorticoid-induced mouse mammary tumor virus gene expression.
2001 Feb 16
Degradation of green tea catechins in tea drinks.
2001 Jan
Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage.
2001 Jan-Feb
Stereospecificity in membrane effects of catechins.
2001 Mar 14
Phase I trial of oral green tea extract in adult patients with solid tumors.
2001 Mar 15
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.
2001 Mar 8
Combination effect of lignin F and natural products.
2001 Mar-Apr
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment to mouse skin prevents UVB-induced infiltration of leukocytes, depletion of antigen-presenting cells, and oxidative stress.
2001 May
Inhibitory effect of epigallocatechin gallate on adhesion of murine melanoma cells to laminin.
2001 Nov 8
Inhibition of UVB-induced oxidative stress-mediated phosphorylation of mitogen-activated protein kinase signaling pathways in cultured human epidermal keratinocytes by green tea polyphenol (-)-epigallocatechin-3-gallate.
2001 Oct 15
Green tea constituent (--)-epigallocatechin-3-gallate inhibits topoisomerase I activity in human colon carcinoma cells.
2001 Oct 19
Simplified catechin-gallate inhibitors of HIV-1 reverse transcriptase.
2001 Oct 22
A novel method of measuring hydroxyl radical-scavenging activity of antioxidants using gamma-irradiation.
2001 Sep
Epigallocatechin gallate (EGCG) inhibits the sulfation of 1-naphthol in a human colon carcinoma cell line, Caco-2.
2001 Sep
Green tea polyphenol (-)-epigallocatechin-3-gallate prevents N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced dopaminergic neurodegeneration.
2001 Sep
Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus.
2001 Sep
The green tea polyphenol (-)-epigallocatechin-3-gallate blocks nuclear factor-kappa B activation by inhibiting I kappa B kinase activity in the intestinal epithelial cell line IEC-6.
2001 Sep
Effects of (-)-epigallocatechin-3-gallate, the main component of green tea, on the cloned rat brain Kv1.5 potassium channels.
2001 Sep 1
Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: down-regulation of COX-2 and iNOS through suppression of NF-kappa B activation.
2001 Sep 1
Inhibitory effects of (-)-epigallocatechin gallate on the life cycle of human immunodeficiency virus type 1 (HIV-1).
2002 Jan
In vitro therapeutic effect of epigallocatechin gallate on nicotine-induced impairment of resistance to Legionella pneumophila infection of established MH-S alveolar macrophages.
2002 Jan 15
Synergistic effects of (-)-epigallocatechin gallate with sulindac against colon carcinogenesis of rats treated with azoxymethane.
2002 Mar 8
Patents

Sample Use Guides

Sunphenon EGCG (Epigallo Catechin Gallate) 200-800mg (1-4 capsules)
Route of Administration: Oral
Epigallocatechin gallate (EGCG) could inhibit the viability and invasion, and induce the apoptosis, of bladder cancer T24 cells. The apoptosis of bladder cancer cells was notably increased by 20 µm EGCG. In addition, 20 µm EGCG inhibited bladder cancer cell viability. However, 10 µm EGCG did not exhibit any significant inhibitory effect on T24 cell viability. The effect of EGCG on the invasive ability of the bladder cancer cells was then investigated, which demonstrated that 10 µm and 20 µm of EGCG significantly inhibited invasion compared with the control group.
Name Type Language
EPIGALLOCATECHIN GALLATE
INCI  
INCI  
Official Name English
(-)-EPIGALLOCATECHIN-3-O-GALLATE (EGCG) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]
Common Name English
(-)-EPIGALLOCATECHIN-3-O-GALLATE [USP-RS]
Common Name English
PF-EGCG 90
Code English
EGCG [MI]
Common Name English
TEAVIGO
Brand Name English
(-)-EPIGALLOCATECHIN-3-O-GALLATE
USP-RS  
Common Name English
EPIGALLOCATECHIN-GALLATE
Common Name English
EGCG
MI   WHO-DD  
Common Name English
EPIGALLOCATECHIN GALLATE [INCI]
Common Name English
NVP-XAA 723
Code English
3-O-GALLOYL-(-)-EPIGALLOCATECHIN
Common Name English
(-)-EPIGALLOCATECHIN GALLATE
Common Name English
BENZOIC ACID, 3,4,5-TRIHYDROXY-, (2R,3R)-3,4-DIHYDRO-5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-2H-1-BENZOPYRAN-3-YL ESTER
Common Name English
EPIGALLOCATECHIN 3-O-GALLATE
Common Name English
EGCG [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68454
Created by admin on Fri Dec 15 15:37:53 GMT 2023 , Edited by admin on Fri Dec 15 15:37:53 GMT 2023
DSLD 2960 (Number of products:2)
Created by admin on Fri Dec 15 15:37:53 GMT 2023 , Edited by admin on Fri Dec 15 15:37:53 GMT 2023
DSLD 1193 (Number of products:210)
Created by admin on Fri Dec 15 15:37:53 GMT 2023 , Edited by admin on Fri Dec 15 15:37:53 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1236700
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PUBCHEM
65064
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NCI_THESAURUS
C1088
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CHEBI
4806
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DRUG BANK
DB12116
Created by admin on Fri Dec 15 15:37:53 GMT 2023 , Edited by admin on Fri Dec 15 15:37:53 GMT 2023
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WIKIPEDIA
EPIGALLOCATECHIN GALLATE
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EPA CompTox
DTXSID1029889
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FDA UNII
BQM438CTEL
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EVMPD
SUB33667
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MERCK INDEX
m4843
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PRIMARY Merck Index
MESH
C045651
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CAS
989-51-5
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RXCUI
24246
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PRIMARY RxNorm
SMS_ID
100000127611
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DAILYMED
BQM438CTEL
Created by admin on Fri Dec 15 15:37:53 GMT 2023 , Edited by admin on Fri Dec 15 15:37:53 GMT 2023
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