oleanolic acid | 262444-35-9

• 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: oleanolic acid
• 英文别名: oleanic acid；12,13-dihydrooleanolic acid；3β-hydroxy-oleanan-28-oic acid；3β-Hydroxy-oleanan-28-saeure；(4aS,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-hexadecahydropicene-4a-carboxylic acid
• CAS: 262444-35-9
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: JKLISIRFYWXLQG-YUOZJKDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  oleanolic acid 在 chromium(VI) oxide 作用下， 生成 3-oxoolean-28-oic acid
  参考文献：
  名称：

  有关三萜的知识。第149部分。将桦木素和齐墩果酸转化为异构体不饱和烃C 29 H 48。关于五环三萜生物合成的假说

  摘要：

  描述了由三萜二醇甜菜碱（I）和齐墩果酸（II）生产异构体不饱和烃IX，XXIV和XXV，并对五环三萜的生物合成进行了假设。

  DOI：

  10.1002/hlca.19500330336
• 作为产物：
  描述：

  3-acetyl 12-oxo-oleanolic acid 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 9.0h， 以72%的产率得到oleanolic acid
  参考文献：
  名称：

  Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents

  摘要：

  Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including D-galactopyranosides, D-glucopyranosides, D-xylopyranoses, D-arabopyranoses and D-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K2CO3, Bu4NBr, CH2Cl2-H2O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1 alpha,25-dihydroxyvitamin D-3 was evaluated in a co-culture assay system. The structure-activity relationships of these compounds were also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.019

文献信息

• Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents
  作者：Jun-Feng Li、Song-Jie Chen、Yu Zhao、Jian-Xin Li

  DOI：10.1016/j.carres.2009.01.019

  日期：2009.3

  Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including D-galactopyranosides, D-glucopyranosides, D-xylopyranoses, D-arabopyranoses and D-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K2CO3, Bu4NBr, CH2Cl2-H2O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1 alpha,25-dihydroxyvitamin D-3 was evaluated in a co-culture assay system. The structure-activity relationships of these compounds were also discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• Zur Kenntnis der Triterpene. 149. Mitteilung. Überführung von Betulin und Oleanolsäure in isomere ungesättigte Kohlenwasserstoffe C₂₉H₄₈. Hypothese über die Biosynthese pentacyclischer Triterpene
  作者：P. Dietrich、O. Jeger

  DOI：10.1002/hlca.19500330336

  日期：——

  Es wurde die Herstellung der isomeren ungesättigten Kohlenwasserstoffe IX, XXIV und XXV aus dem Triterpendiol Betulin (I) und der Oleanolsäure (II) beschrieben und eine Hypothese über die Biosynthese pentacyclischer Triterpene aufgestellt.

  描述了由三萜二醇甜菜碱（I）和齐墩果酸（II）生产异构体不饱和烃IX，XXIV和XXV，并对五环三萜的生物合成进行了假设。