4-hydroxy-11(13)-eudesmen-12-oic acid | 4586-68-9

• 物质功能分类: 天然产物 - 倍半萜
• 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: 4-hydroxy-11(13)-eudesmen-12-oic acid
• 英文别名: methyl (2E)-2-[(2R,4aR,8R,8aR)-8-hydroxy-4a,8-dimethyl-decahydronaphthalen-2-yl]prop-2-enoate；2-[(2R,4aR,8R,8aR)-8-hydroxy-4a,8-dimethyl-decahydronaphthalen-2-yl]prop-2-enoic acid；ilicic acid；2-[(2R,4aR,8R,8aR)-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
• CAS: 4586-68-9
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: FXKCXGBBUBCRPU-QHSBEEBCSA-N

物化性质

• 熔点：
  173-175 °C
• 沸点：
  399.4±25.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090
• 储存条件：
  存放温度应控制在2-8℃，需保持干燥并密封保存。

制备方法与用途

ilicic酸是一种倍半萜内酯，可以从樟脑中分离得到。

反应信息

• 作为反应物：
  描述：

  4-hydroxy-11(13)-eudesmen-12-oic acid 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 柳杉二醇
  参考文献：
  名称：

  Short and efficient hemisynthesis of α-eudesmol and cryptomeridiol

  摘要：

  The aerial part of Dittrichia viscosa yielded two sesquiterpenes, isocostic acid (1) and ilicic acid (2), on multigram scale. These acids are appropriate starting materials for short and facile syntheses of a-eudesmol (5) and cryptomeridiol (6), natural products featuring anti-Alzheimer and anti-spasmodic properties. Compounds 5 and 6 were obtained in three steps in overall yields of 70% and 52%, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.064

文献信息

• Modification of Natural Eudesmane Scaffolds via Mizoroki-Heck Reactions
  作者：Mohamed Zaki、Mohamed Akssira、Sabine Berteina-Raboin

  DOI：10.3390/molecules22040652

  日期：——

  The Mizoroki-Heck reaction was applied to substrates derived from isocostic and ilicic acids, important sesquiterpene components of Dittrichia viscosa L. Greuter that were extracted directly from plant material collected in Morocco. After optimization of the metallo-catalysis conditions, various aryl-groups were successfully introduced on the exocyclic double bond with an exclusive E-configuration

  将Mizoroki-Heck反应应用于衍生自等椰子油和二十二酸的基质，这是从摩洛哥收集的植物材料中直接提取的，Dittrichia viscosa L. Greuter的重要倍半萜烯成分。在优化金属催化条件后，各种环芳基以独特的E构型成功地引入到环外双键上，并且没有外消旋作用。
• <i>N</i>-Acylvanillamides:  Development of an Expeditious Synthesis and Discovery of New Acyl Templates for Powerful Activation of the Vanilloid Receptor
  作者：Giovanni Appendino、Alberto Minassi、Aniello Schiano Morello、Luciano De Petrocellis、Vincenzo Di Marzo

  DOI：10.1021/jm020844o

  日期：2002.8.1

  A simple and general synthesis of vanillamides was developed and employed to screen acids from the fatty and isoprenoid pools for new acyl templates of biological relevance as capsaicin analogues. Potent activation of the human vanilloid receptor 1 (VR1) was observed for the vanillamides of certain polyfunctional acids from both pools, showing that the vanilloid activity of capsaicinoids can be. substantially improved by introducing polar groups and/or unsaturations on the acyl moiety. The activity of the unsaturated analogues was maintained or even increased by cyclopropAnation, while omega dimerization led to a substantial increase of activity. Because of the Wide structural diversity of the library of compounds screened, these observations could not be translated into a single framework of structure-activity relationships. Nevertheless, a series of new highly active leads was identified, validating the pharmacological potential of the unnatural combination of natural building blocks to provide new bioactive compounds.
• Tessaric acid derivatives induce G2/M cell cycle arrest in human solid tumor cell lines
  作者：Leticia G. León、Osvaldo J. Donadel、Carlos E. Tonn、José M. Padrón

  DOI：10.1016/j.bmc.2009.07.053

  日期：2009.9.1

  A series of analogs were synthesized in a straightforward manner from naturally available sesquiterpenes ilicic acid and tessaric acid. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, HBL-100, HeLa, SW1573, T-47D and WiDr. The most potent analog induced considerably growth inhibition in the range 1.9-4.5 mu M. Cell cycle studies for tessaric acid derivatives indicated a prominent arrest of the cell cycle at the G(2)/M phase. Damage to the cells was permanent as determine by the so called 24+24 drug schedule. (C) 2009 Elsevier Ltd. All rights reserved.
• Structure of the sesquiterpene hydroxyacid fromArtemisia vachanica Krasch
  作者：N. A. Kechatova、A. I. Ban'kovskii、V. I. Sheichenko、K. S. Rybalko

  DOI：10.1007/bf00563694

  日期：1965.9
• Daniewski, Wlodzimierz M.; Kroszczynski, Wojciech; Bloszyk, Elzbieta, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 8, p. 1710 - 1721
  作者：Daniewski, Wlodzimierz M.、Kroszczynski, Wojciech、Bloszyk, Elzbieta、Drozdz, Bohdan、Nawrot, Jan、et al.

  DOI：——

  日期：——