(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(Z)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylic acid

• ChemBase编号: 177412
• 分子式: C20H20O9
• 平均质量: 404.3674
• 单一同位素质量: 404.11073222
• SMILES: O([C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)c1cc(cc(c1)/C=C\c1ccc(cc1)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2cc(/C=C\c3ccc(cc3)O)cc(c2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H20O9/c21-12-5-3-10(4-6-12)1-2-11-7-13(22)9-14(8-11)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)/b2-1-/t15-,16-,17+,18-,20+/m0/s1
• InChIKey: QWSAYEBSTMCFKY-BMPGWQKJSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(Z)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylic acid
• IUPAC传统名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(Z)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylic acid
• 别名: 3-Hydroxy-5-[(1Z)-2-(4-hydroxyphenyl)ethenyl]phenyl β-D-Glucopyranosiduronic Acid; cis-Resveratrol 3-O-β-D-Glucuronide (contains up to 15% trans isomer)

登记号

• CAS号: 387372-23-8
• PubChem SID: 164233322
• PubChem CID: 29986850

理论计算性质

• Acid pKa: 3.1353626
• 质子受体: 9
• 质子供体: 6
• LogD (pH = 5.5): -0.88327813
• LogD (pH = 7.4): -2.0100691
• Log P: 1.4545974
• 摩尔折射率: 99.4673 cm^3
• 极化性: 38.91712 Å^3
• 极化表面积: 156.91 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Off-White Solid
• 熔点: 118-120°C

安全信息

• 保存条件: Amber Vial, -86°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - R150010

A metabolite of cis Resveratrol.

参考文献

• Yu, C., et al.: Pharm. Res., 19, 1907 (2001)
• Rimando, A., et al.: J. Agric. Food Chem., 52, 4713 (2001)
• Walle, T., et al.: Drug Metab. Dispos., 32, 1377 (2001)
• Ito, H., et al.: Br. J. Nutr., 94, 500 (2
• Schroder, H., et al.: Clin. Nutr., 20, 429 (2001)