(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

• ChemBase编号: 72911
• 分子式: C22H18O11
• 平均质量: 458.37172
• 单一同位素质量: 458.0849114
• SMILES: c1(c(c(cc(c1)C(=O)O[C@H]1[C@H](Oc2c(C1)c(cc(c2)O)O)c1cc(c(c(c1)O)O)O)O)O)O
• Canonical SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1cc(O)c(c(c1)O)O
• InChI: 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

名称和登记号

名称

• IUPAC标准名: (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• IUPAC传统名: (-)-epigallocatechin gallate; (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• 别名: (-)-顺式-2-(3,4,5-三羟基苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7--三醇 3-没食子酸酯; (-)-顺式-3,3′,4′,5,5′,7-六羟基-黄烷-3-没食子酸酯; (-)-表没食子儿茶素没食子酸酯; (-)-Epigallocatechin gallate; (-)-Epigallocatechin gallate; Epigallocatechin gallate; (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate; EGCG; (-)-Epigallocatechin gallate; 3-O-(4-Hydroxybenzoyl)epigallocatechin; EGCG (Epigallocatechin gallate ); Teavigo; epi-Gallocatechin 3-O-Gallate; epi-Gallocatechin Gallate; Epigallocatechin-3-monogallate; L-Epigallocatechin Gallate; 3-O-Galloyl-(-)-epigallocatechin; (-)-cis-3,3′,4′,5,5′,7-Hexahydroxy-flavane-3-gallate; (-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate

登记号

• CAS号: 989-51-5
• MDL号: MFCD00075940
• PubChem SID: 162037831; 24873355; 24894544; 24894548
• PubChem CID: 65064
• CHEBI ID: 4806
• CHEMBL: 297453
• Chemspider ID: 58575
• 医学主题词(MeSH): Epigallocatechin+gallate
• 维基百科标题: Epigallocatechin_gallate

理论计算性质

• Acid pKa: 7.9929934
• 质子受体: 10
• 质子供体: 8
• LogD (pH = 5.5): 3.0747623
• LogD (pH = 7.4): 2.9740098
• Log P: 3.0761456
• 摩尔折射率: 111.7453 cm^3
• 极化性: 42.63128 Å^3
• 极化表面积: 197.37 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Methanol; soluble in ethanol, DMSO, dimethyl formamide at about 20 g/l; soluble in water
• 外观: ''; Light Pink Solid
• 熔点: 216-218°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: KB5200000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... CYP1A2(1544)
• 生物活性机理: Shows anti-HIV activity. Tumour promotion inhibitor, putative cancer chemopreventive agent. Implicated in occup. asthma in green tea factories

产品相关信息

• 纯度: ≥80% (HPLC); ≥95%; ≥97.0% (HPLC); ≥98.0% (HPLC)
• 级别: analytical standard; purum
• 成盐信息: Free Base
• 生物来源: from green tea; Green Tea
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antioxidant
• Empirical Formula (Hill Notation): C22H18O11

详细说明

Selleck Chemicals - S2250

Research Area: Infection
Biological Activity:
(-)-Epigallocatechin gallate is a potent anti-oxidant polyphenol flavonoid isolated from green tea. It is the ester of epigallocatechin and gallic acid, and is a type of catechin. Its possible benefit as a nutritional chemopreventive agent for cancer, atherosclerosis, and neurodegenerative diseases is generating increased scientific interest. EGCG has demonstrated chemopreventive and chemotherapeutic actions in cellular and animal models of cancer. [1][2]

Sigma Aldrich - E4268

Biochem/physiol Actions
Catechins are a plant derived polyphenolic anti-oxidants with phytotoxic properties. Racemic catechin may be used in studies on seed germination and plant invasiveness. Catechin and Epigallocatechin gallate (EGCG) may be used with other polyphenol flavonoids to study their effects in oxidation and peroxidation-related processes.

Sigma Aldrich - E4143

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Antioxidant polyphenol flavonoid that inhibits telomerase and DNA methyltransferase. EGCG blocks the activation of EGF receptors and HER-2 receptors. ECGG inhibits fatty acid synthase and glutamate dehydrogenase activity.

Toronto Research Chemicals - E588500

(-)-Epigallocatechin Gallate 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.

参考文献

• Katiyar S et al. J Nutr Biochem. 2007 May;18(5):287-96.
• Yamane, T. et al.: Cancer Res., 55, 2081 (1995)
• Tan, J. et al.: J. Neurosci. 25, 8807 (1995)
• Nakane, H., Biochemistry, 1990, 29, 2841, (anti-HIV activity)
• Lee, M.W. et al., Phytochemistry, 1992, 31, 2117, (gallates)
• Fujiki, H. et al., Prev. Med., 1992, 21, 503, (gallate, pharmacol, rev)