Epigallocatechin Gallate (HCID 65064)

Overview

(-)-epigallocatechin 3-gallate is a gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of ()-epigallocatechin. It has a role as a geroprotector, an antioxidant, an antineoplastic agent, a neuroprotective agent, a Hsp90 inhibitor, an apoptosis inducer and a plant metabolite. It is a polyphenol, a gallate ester and a member of flavans. It is functionally related to a (-)-epigallocatechin.

Names & identifiers

Preferred name: Epigallocatechin Gallate
IUPAC: [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
English name: (-)-Epigallocatechin gallate
Molecular formula: C22H18O11
Molecular weight: 458.37

Names & synonyms

(-)-Epigallocatechin gallate989-51-5EGCGEpigallocatechin gallateEpigallocatechin-3-gallateTea catechin(-)-Epigallocatechin-3-o-gallateTeavigo(-)-Epigallocatechol gallateDTXSID1029889L-Epigallocatechin gallatePF-EGCg 90

Show more names

ECGC(-)-Epigallocatechin-3-O-gallate (20 mg)epigallocatechin3-gallateEpigallocatechin-3-Monogallate(-)-epigallocatechin 3-gallateEGCG, (-)-Epigallocatechin gallate/Green Tea EGCG90

NVP-XAA 723BQM438CTELepigallocatechin-3-O-gallate(-)-Epigallocatechin-3-gallateEpigallocatechin-gallateEPIGALLOCATECHIN 3-O-GALLATEDTXCID80567CHEBI:4806

Database identifiers

CAS: 989-51-5
PubChem CID: 65064
DTXSID: DTXSID1029889
ChEMBL: CHEMBL297453
ChEBI: CHEBI:4806
UNII: BQM438CTEL
EC Number: 479-560-7、619-381-5
Nikkaji: J134.058A

Properties

Computed structural properties

XLogP: 1.2
Topological polar surface area: 197 Å²
Hydrogen bond donors: 8
Hydrogen bond acceptors: 11
Rotatable bonds: 4
Heavy atoms: 33
Formal charge: 0
Complexity: 667

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Proanthocyanidins [PK1203]

LogP1.08

Melting Point140 - 142 °C

Physical DescriptionSolid

Collision Cross Section · 3 items

212.4 Å² [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1029889]

209.87 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

206.1 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 222 · 222-224°C
alpha: -185 · D -185 ±2°(ethanol)
refractive index: -175.5 ° · -175.5 ° (C=1, EtOH)
storage temp.: 2 · 2-8°C
solubility: 2 O: · H2O: ≥5mg/mL, clear
Boiling point: 909.1 · 909.1±65.0 °C(Predicted)
Density: 1.9 · 1.90±0.1 g/cm3(Predicted)
pka: 7.75 · 7.75±0.25(Predicted)
form: Solid
color: White to Light Brown
biological source: green tea
Water Solubility: Soluble in ethanol, dimethyl formamide, water.
Merck: 14 · 14,3526
Stability: Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
Major Application: metabolomicsvitamins, nutraceuticals, and natural products
Cosmetics Ingredients Functions: ANTIOXIDANT
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
InChIKey: WMBWREPUVVBILR-WIYYLYMNSA-N
SMILES: Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4cc(O)c(O)c(O)c4
LogP: 0.639 · 0.639 (est)
CAS DataBase Reference: 989 · 989-51-5(CAS DataBase Reference)
EWG's Food Scores: 2 · 2
NCI Dictionary of Cancer Terms: -3 · EGCG; epigallocatechin-3-gallate
FDA UNII: 438 CTEL · BQM438CTEL
NCI Drug Dictionary: epigallocatechin gallate
UNSPSC Code: 85151701 · 85151701
NACRES: 79 · NA.79
Symbol(GHS): 7 · GHS07,GHS09
Signal word: Warning
Hazard statements: 302 · H302-H317-H319-H411
Precautionary statements: 261 · P261-P273-P280-P301+P312-P302+P352-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 24 · 24/25
WGK Germany: 2 · 2
RTECS: 5200000 · KB5200000
F: 10 · 10-23
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2Skin Sens. 1
Toxicity: 50 oral · LD50 oral in mouse: 2170mg/kg
REACH Registrations: Inactive

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 18.2% (2 of 11) of reports.

Warning

H302 (72.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 11 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 60% (6 of 10) of all reports.

Hazard information

Regulatory Information · 2 items

Regulation (EC) No 178/2002 (amended)

Status: Active Update: 12-01-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/8734

Hazard Classes and Categories · 2 items

Acute Tox. 4 (30%)

Acute Tox. 4 (72.7%)

Safety data

F: 10-23
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 2
rtecs: KB5200000
hs_code: 29339900
Toxicity: LD50 oral in mouse: 2170mg/kg
Signal word: Warning
Symbol(GHS): GHS07,GHS09
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H317-H319-H411
REACH Registrations: Inactive
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2Skin Sens. 1
Precautionary statements: P261-P273-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Metabolism/Metabolites(-)-Epigallocatechin gallate has known human metabolites that include (-)-Epigallocatechin gallate, 3p-hydroxy-glucuronide and (-)-Epigallocatechin gallate, 4p-hydroxy-glucuronide.

MeSH Pharmacological Classification · 4 items

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved.

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.

Tissue LocationsBladder

Cellular LocationsMembrane

Applications · 6 items

Uses(-)-Epigallocatechin Gallate (egcg) is a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-ß and amaloid plaques in mice. This compound has neuroprotective properties.

Usestelomerase inhibitor

UsesAn inhibitor of Bcl-2 and NOS2

UsesA tumor-inhibiting constituent of green tea. Alters the cleavage of amyloid precursor protein, decreasing production of amaloid- and amaloid plaques in mice

Uses(-)-Epigallocatechin Gallate (egcg) is a tumor-inhibiting constituent of green tea. (-)-Epigallocatechin Gallate alters the cleavage of amyloid precursor protein, decreasing production of amaloid-β and amaloid plaques in mice. This compound has neuroprotective properties.

General DescriptionPharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.Epigallocatechin gallate is a potent polyphenolic flavonoid which is found as a component of tea. It exhibits antioxidant, antimutagenic, antitumor and anti-inflammatory properties, thereby contributing to the health-beneficial actions. It finds potential use as a drug candidate in the pharmaceutical, cosmetic, and nutritional fields.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes · 1 item

DefinitionChEBI: (-)-epigallocatechin 3-gallate is a gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin. It has a role as an antineoplastic agent, an antioxidant, a Hsp90 inhibitor, a neuroprotective agent, a plant metabolite, a geroprotector and an apoptosis inducer. It is a gallate ester, a polyphenol and a member of flavans. It is functionally related to a (-)-epigallocatechin.