Epigallocatechin Gallate (HCID 65064)

Überblick

(-)-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.

Namen und Bezeichner

Bevorzugter 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
Englischer Name: (-)-Epigallocatechin gallate
Summenformel: C22H18O11
Molmasse: 458.37

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,2
Polarare Oberfläche (TPSA): 197 Å²
H-Brücken-Donoren: 8
H-Brücken-Akzeptoren: 11
Frei drehbare Bindungen: 4
Schwere Atome: 33
Formalladung: 0
Komplexität: 667

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

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

LogP1.08

Melting Point140 - 142 °C

Physical DescriptionSolid

Collision Cross Section · 3 Einträge

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]

Physikochemische Eigenschaften

Schmelzpunkt: 222 · 222-224°C
Brechungsindex: -175.5 ° · -175.5 ° (C=1, EtOH)
storage temp.: 2 · 2-8°C
Löslichkeit: 2 O: · H2O: ≥5mg/mL, clear
Siedepunkt: 909.1 · 909.1±65.0 °C(Predicted)
Dichte: 1.9 · 1.90±0.1 g/cm3(Predicted)
pka: 7.75 · 7.75±0.25(Predicted)
Aggregatzustand: Solid
Farbe: White to Light Brown
Biologische Quelle: green tea
Wasserlöslichkeit: Soluble in ethanol, dimethyl formamide, water.
Merck: 14 · 14,3526
Stabilität: Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
Major Application: metabolomicsvitamins, nutraceuticals, and natural products
Kosmetik-Inhaltsstoffe Funktionen: 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 Datenbank: 989 · 989-51-5(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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.

Gefahrenhinweise

Regulatory Information · 2 Einträge

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 Einträge

Acute Tox. 4 (30%)

Acute Tox. 4 (72.7%)

Sicherheitsdaten

F: 10-23
wgk: 2
hs_code: 29339900
RTECS-Nr.: KB5200000
Toxizität: LD50 oral in mouse: 2170mg/kg
safety_code: 24/25
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2Skin Sens. 1

Chemie und Industrie

Pharmakologische Informationen

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 Einträge

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

Anwendungen · 1 Eintrag

Verwenden(-)-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.