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

• ChemBase编号: 127266
• 分子式: C22H18O10
• 平均质量: 442.37232
• 单一同位素质量: 442.08999678
• SMILES: O=C(O[C@@H]1Cc2c(O[C@@H]1c1ccc(O)c(O)c1)cc(O)cc2O)c1cc(O)c(O)c(O)c1
• Canonical SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
• InChIKey: LSHVYAFMTMFKBA-TZIWHRDSSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
• IUPAC传统名: (-)-epicatechin 3-O-gallate
• 别名: (-)-表儿茶素没食子酸酯; ECG; Epicatechin 3-gallate; (-)-Epicatechin-3-O-gallate; Epicatechin gallate; 3,4,5-Trihydroxybenzoic Acid (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl Ester; (-)-epi-Catechin 3-O-gallate; 3-Galloyl-(-)-epicatechin; 3-Galloyl-(2R,3R)-(-)-Epicatechin; (-)-Epicatechin Gallate; (-)-cis-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate; (-)-cis-3,3′,4′,5,7-Pentahydroxyflavane 3-gallate; (-)-Epicatechin gallate

登记号

• CAS号: 1257-08-5
• MDL号: MFCD00075936
• PubChem SID: 24894531; 162221587
• PubChem CID: 107905
• CHEMBL: 36327
• Chemspider ID: 97034
• 维基百科标题: Epicatechin_gallate

理论计算性质

• Acid pKa: 8.03228
• 质子受体: 9
• 质子供体: 7
• LogD (pH = 5.5): 3.3784473
• LogD (pH = 7.4): 3.2868483
• Log P: 3.379711
• 摩尔折射率: 109.7644 cm^3
• 极化性: 41.964565 Å^3
• 极化表面积: 177.14 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: DH9030000
• 德国WGK号: 3
• 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)

产品相关信息

• 纯度: ≥98% (HPLC); ≥98.0% (HPLC)
• 级别: purum
• 生物来源: from green tea
• Empirical Formula (Hill Notation): C22H18O10

详细说明

Sigma Aldrich - E3893

Biochem/physiol Actions
抗氧化剂

Toronto Research Chemicals - E582265

One of the catechin isomers and a potent antioxidant that can modulate a wide range of membrane proteins. Its bilayer-modifying potency was tested using gramicidin A (gA) channels as probes. All the catechins alter gA channel function and modify bilayer p

参考文献

• Ingolfsson, H., et al.: FEBS Lett., 585, 3101 (2011)