1β,3β,4β-trihydroxy-5α-{[3-[4-[1β-(6-O-(5-(E)-caffeoylquinic acid)-β-D-glucopyranosyl)oxy]-3-hydroxyphenyl]-(E)-1-oxo-2-propenyl]oxy}cyclohexanecarboxylic acid | 1416363-81-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 1β,3β,4β-trihydroxy-5α-{[3-[4-[1β-(6-O-(5-(E)-caffeoylquinic acid)-β-D-glucopyranosyl)oxy]-3-hydroxyphenyl]-(E)-1-oxo-2-propenyl]oxy}cyclohexanecarboxylic acid
• 英文别名: viarumacid A；(1S,3R,4R,5R)-3-[(E)-3-[4-[(2S,3R,4S,5S,6R)-6-[[(1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexanecarbonyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyphenyl]prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• CAS: 1416363-81-9
• 化学式: C₃₈H₄₄O₂₂
• 分子量: 852.754
• InChiKey: MEGCMHCHWAMJBV-QCNSHTHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  60
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  377
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  1β,3β,4β-trihydroxy-5α-{[3-[4-[1β-(6-O-(5-(E)-caffeoylquinic acid)-β-D-glucopyranosyl)oxy]-3-hydroxyphenyl]-(E)-1-oxo-2-propenyl]oxy}cyclohexanecarboxylic acid 在 盐酸 、 水 作用下， 生成 可得然胶
  参考文献：
  名称：

  Antioxidant Glucosylated Caffeoylquinic Acid Derivatives in the Invasive Tropical Soda Apple, Solanum viarum

  摘要：

  Eggplant and related Solanum species contain abundant caffeoylquinic acid (CQA) derivatives. Fruit of the invasive species Solanum viarum Dunal contain numerous complex CQA derivatives, but only a few have been identified. The structures of two new compounds isolated from methanolic extracts of S. viarum fruit by C-18-HPLC-DAD were determined using 2D NMR and MS data. Both include two 5-CQA molecules joined by glucose via ester and glycosidic linkages. The structures of compounds 1 and 2 (viarumacids A and B) are, respectively, 5-caffeoyl- and 3-malonyl-5-caffeoyl-[4-(1 beta-[6-(5-caffeoyl)quinate]glucopyranosyl)]quinic acid. The antioxidant activities determined by ABTS(center dot+) and DPPH center dot assays were in the order 1 > 2 > 5-CQA.

  DOI：

  10.1021/np300553t