(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

• ChemBase编号: 127523
• 分子式: C15H14O7
• 平均质量: 306.26746
• 单一同位素质量: 306.07395279
• SMILES: O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1
• Canonical SMILES: Oc1cc2O[C@H](c3cc(O)c(c(c3)O)O)[C@@H](Cc2c(c1)O)O
• InChI: InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1
• InChIKey: XMOCLSLCDHWDHP-IUODEOHRSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC传统名: epigallocatechin
• 别名: (-)-cis-2-(3,4,5-三羟基苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7-三醇; (-)-表没食子儿茶素; (2R,3R)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triol; Epigallocatechol; l-Gallocatecholl); (-)-3,3',4',5,5',7-Flavanhexol; (-)-Epigallocatechol; (-)-epi-Gallocatechin; (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-trihydroxychroman; 1-epi-3',4',5',5,7-Pentahydroxy-3-flavanol; 3,3',4',5,5',7-Flavanhexol; Antiscurvy factor C2; EGC; Galloepicatechin; L-Epigallocatechin; NSC 674039; Sunphenon EGC; epi-Gallocatechin; l-Epigallocatechol; (-)-Epigallocatechin; epigallocatechin; (+)-gallocatechin; Gallocatechol; (-)-cis-3,3′,4′,5,5′,7-Hexahydroxyflavane; (-)-Epigallocatechin; (-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; Epigallocatechin

登记号

• CAS号: 970-74-1; 1617-55-6
• MDL号: MFCD00075939
• PubChem SID: 24894529; 24846148; 162221842
• PubChem CID: 72277; 65084
• CHEMBL: 47386
• 医学主题词(MeSH): Gallocatechol
• 维基百科标题: Gallocatechol

理论计算性质

• Acid pKa: 8.728533
• 质子受体: 7
• 质子供体: 6
• LogD (pH = 5.5): 1.4912869
• LogD (pH = 7.4): 1.4716134
• Log P: 1.4915417
• 摩尔折射率: 75.9806 cm^3
• 极化性: 29.079527 Å^3
• 极化表面积: 130.61 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: false

分子性质

理化性质

• 外观: Powder

安全信息

• 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: ≥90% (HPLC); ≥95% (HPLC); 98.0
• 级别: analytical standard
• 生物来源: from green tea
• Empirical Formula (Hill Notation): C15H14O7

详细说明

Sigma Aldrich - 08108

Biochem/physiol Actions
Green tea polyphenol. Anticancer agent. Lower antioxidant activity than EGCG.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - E3768

Biochem/physiol Actions
Green tea polyphenol. Anticancer agent. Lower antioxidant activity than EGCG.
抗氧化剂
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Toronto Research Chemicals - E588490

A natural constituent of green tea. It is an antioxidant and a potential cancer chemopreventive agent. An epimer of (-)-Gallocatechin (G188990).

参考文献

• Kalaivani, M. et al.: J. Pharm. Res., 3, 2901 (2010)
• Letchoumy, P.V. et al.: Arch. Med. Sci., 3, 330 (2010)
• Zhu, N. et al.: J. Food Lipids, 7, 275 (2010)