8-epi-kingisidic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-epi-kingisidic acid
• 英文别名: (1R,4aS,8S,8aS)-1-methyl-3-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,8,8a-tetrahydro-1H-pyrano[3,4-c]pyran-5-carboxylic acid
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: HQEBQNGGKFIFBW-SDESGXHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (4S,5S,6S)-4-Carboxymethyl-5-[(S)-1-(2,3-dihydroxy-2-methyl-butyryloxy)-ethyl]-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid 在 六甲基磷酰三胺 、 氢氧化钾 作用下， 以 水 为溶剂， 以356 mg的产率得到kingisidic acid
  参考文献：
  名称：

  A secoiridoid and other constituents of Gonocaryum calleryanum

  摘要：

  Investigation of the leaves, branch, stem and root bark of Gonocaryum calleryanum resulted in the isolation of a new secoiridoid glycoside, gonocaryoside E, together with 14 known compounds. Their structures were elucidated by spectral analysis and chemical transformation. Gonocaryoside E was shown to be a derivative of kingiside in which the lactone ring was open, and with the 8-hydroxy group esterified with tiglic acid. Alkaline hydrolysis of these secoiridoids is discussed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)80075-7