Epigallocatechin Gallate (HCID 65064)

概要

(-)-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.

名称と識別子

優先名称: Epigallocatechin Gallate
IUPAC: [(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
現地名: (-)-没食子酸エピガロカテキン水和物
英語名: (-)-Epigallocatechin gallate
分子式: C22H18O11
分子量: 458.37

名称と別名

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

名称をさらに表示

(-)-没食子酸エピガロカテキン水和物2α-(3,4,5-トリヒドロキシフェニル)-3α-(3,4,5-トリヒドロキシベンゾイルオキシ)クロマン-5,7-ジオール2α-(3,4,5-トリヒドロキシフェニル)クロマン-3α,5,7-トリオール3-(3,4,5-トリヒドロキシベンゾアート)3,4,5-トリヒドロキシ安息香酸(2R)-2α-(3,4,5-トリヒドロキシフェニル)-5,7-ジヒドロキシ-3,4-ジヒドロ-2H-1-ベンゾピラン-3α-イルエピガロカテキン3-ガラート3,4,5-トリヒドロキシ安息香酸2α-(3,4,5-トリヒドロキシフェニル)-3,4-ジヒドロ-5,7-ジヒドロキシ-2H-1-ベンゾピラン-3α-イル(2R)-2α-(3,4,5-トリヒドロキシフェニル)-3α-(3,4,5-トリヒドロキシベンゾイルオキシ)-3,4-ジヒドロ-2H-1-ベンゾピラン-5,7-ジオール3,4,5-トリヒドロキシ安息香酸[(2R,3R)-3,4-ジヒドロ-5,7-ジヒドロキシ-2α-(3,4,5-トリヒドロキシフェニル)-2H-1-ベンゾピラン-3α-イル](-)-エピガロカテキンガラート(2R,3R)-2-(3,4,5-トリヒドロキシフェニル)-3-(3,4,5-トリヒドロキシベンゾイルオキシ)-3,4-ジヒドロ-2H-1-ベンゾピラン-5,7-ジオール(-)-エピガロカテキン3-O-ガラート(-)-エピガロカテキン-3-O-ガラートエピガロカテキンガラート(-)-エピガロカテキン3-ガラート(-)-エピガロカテキン-3-ガラート3-O-ガロイルエピガロカテキン(-)-3,4,5-トリヒドロキシ安息香酸[(2R)-3,4-ジヒドロ-5,7-ジヒドロキシ-2α-(3,4,5-トリヒドロキシフェニル)-2H-1-ベンゾピラン]-3α-イル(2R)-3,4-ジヒドロ-2α-(3,4,5-トリヒドロキシフェニル)-2H-1-ベンゾピラン-3α,5,7-トリオール3-(3,4,5-トリヒドロキシベンゾアート)3,4,5-トリヒドロキシ安息香酸(2R,3R)-2-(3,4,5-トリヒドロキシフェニル)-5,7-ジヒドロキシ-3,4-ジヒドロ-2H-1-ベンゾピラン-3-イル3,4,5-トリヒドロキシ安息香酸(2R)-3,4-ジヒドロ-5,7-ジヒドロキシ-2α-(3,4,5-トリヒドロキシフェニル)-2H-1-ベンゾピラン-3α-イル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

データベース識別子

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

物性

構造計算による物性

XLogP: 1.2
極性表面積: 197 Å²
水素結合供与体数: 8
水素結合受容体数: 11
回転可能結合数: 4
重原子数: 33
形式電荷: 0
複雑度: 667

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

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

LogP1.08

Melting Point140 - 142 °C

Physical DescriptionSolid

Collision Cross Section · 3 件

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]

物理化学的性質

融点: 222 · 222-224°C
比旋光度: -185 · D -185 ±2°(ethanol)
屈折率: -175.5 ° · -175.5 ° (C=1, EtOH)
貯蔵温度: 2 · 2-8°C
溶解性: 2 O: · H2O: ≥5mg/mL、透明
沸点: 909.1 · 909.1±65.0 °C(Predicted)
比重(密度): 1.9 · 1.90±0.1 g/cm3(Predicted)
酸解離定数(Pka): 7.75 · 7.75±0.25(Predicted)
外見: Solid
色: 白から薄茶色
由来生物: green tea
水溶解度: エタノール、ジメチルホルムアミド、水に可溶。
Merck: 14 · 14,3526
安定性: 安定していますが、光に敏感な場合があります。強力な酸化剤とは相容れない。
主な用途: メタボロミクスビタミン、栄養補助食品、天然製品
化粧品成分の機能: 抗酸化物質
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 データベース: 989 · 989-51-5(CAS DataBase Reference)

化学的性質

化学的特性solid

安全と法規制

GHS分類

GHS Classification · 6 件

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.

危険有害性情報

Regulatory Information · 2 件

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 件

Acute Tox. 4 (30%)

Acute Tox. 4 (72.7%)

安全データ

F: 10-23
wgk: 2
rtecs: KB5200000
毒性: LD50 oral in mouse: 2170mg/kg
hs_code: 29339900
safety_code: 24/25
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2Skin Sens. 1
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

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 件

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

応用分野 · 3 件

用途薬理研究用、ポリフェノール研究用。

使用(-)-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.

一般的な説明Pharmaceutical 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.