ketologanic acid | 170382-11-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ketologanic acid
• 英文别名: 7-ketologanic acid；(1S,4aS,7R,7aS)-7-methyl-6-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• CAS: 170382-11-3
• 化学式: C₁₆H₂₂O₁₀
• 分子量: 374.345
• InChiKey: HGYUBLMQZDQRSI-PZGZDOIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  26
• 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：
  163
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ketologanic acid 、 重氮甲烷 生成 7-ketologanin
  参考文献：
  名称：

  ANIKINA, E. V.;SYRCHINA, A. I.;VERESHCHAGIN, A. L.;LARIN, M. F.;SEMENOV, +, XIMIYA PRIROD. SOED.,(1988) N 4, S. 598-599

  摘要：

  DOI：
• 作为产物：
  描述：

  7-ketologanin 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以100 g的产率得到ketologanic acid
  参考文献：
  名称：

  Biosynthesis of iridoids in Syringa and Fraxinus: Carbocyclic iridoid precursors

  摘要：

  Feeding experiments with deuterium-labelled precursors to Fraxinus excelsior, Syringa josikaea and S. vulgaris have shown that the biosynthesis of the oleoside-type secoiridoids (e.g. oleuropein) proceeds via iridodial, iridotrial, deoxy-loganic acid aglucon and deoxy-loganic acid. Hydroxylation of the 7 alpha-position is followed by oxidation and methylation of C-11 to give 7-ketologanin, the last carbocyclic iridoid precursor of the oleosides. The sequences of the steps between deoxy-loganic acid and 7-ketologanin may differ with plant species and time of year. 8-Epi-kingisidic acid and 8-epi-kingiside can be formed from 8-ketologanic acid (and its methyl ester). The secoiridoids, fliederoside and lilacoside, from S. vulgaris have been characterized.

  DOI：

  10.1016/0031-9422(95)00210-x

文献信息

• ANIKINA, E. V.;SYRCHINA, A. I.;VERESHCHAGIN, A. L.;LARIN, M. F.;SEMENOV, +, XIMIYA PRIROD. SOED.,(1988) N 4, S. 598-599
  作者：ANIKINA, E. V.、SYRCHINA, A. I.、VERESHCHAGIN, A. L.、LARIN, M. F.、SEMENOV, +

  DOI：——

  日期：——
• Biosynthesis of iridoids in Syringa and Fraxinus: Carbocyclic iridoid precursors
  作者：Søren Damtoft、Henrik Franzyk、Søren Rosendal Jensen

  DOI：10.1016/0031-9422(95)00210-x

  日期：1995.10

  Feeding experiments with deuterium-labelled precursors to Fraxinus excelsior, Syringa josikaea and S. vulgaris have shown that the biosynthesis of the oleoside-type secoiridoids (e.g. oleuropein) proceeds via iridodial, iridotrial, deoxy-loganic acid aglucon and deoxy-loganic acid. Hydroxylation of the 7 alpha-position is followed by oxidation and methylation of C-11 to give 7-ketologanin, the last carbocyclic iridoid precursor of the oleosides. The sequences of the steps between deoxy-loganic acid and 7-ketologanin may differ with plant species and time of year. 8-Epi-kingisidic acid and 8-epi-kingiside can be formed from 8-ketologanic acid (and its methyl ester). The secoiridoids, fliederoside and lilacoside, from S. vulgaris have been characterized.