冬青醇 | 72715-02-7

• 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
• 中文名称: 冬青醇
• 英文名称: 4α-hydroxy-4β-methyldihydrocostol
• 英文别名: ilicol；(1R,4aR,7R,8aR)-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethyl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-ol
• CAS: 72715-02-7
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: RMARCXQAHOJNRB-KBUPBQIOSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  350.9±25.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

制备方法与用途

用途

冬青醇是一种植物提取物，可用作标准品、对照品。  

反应信息

• 作为反应物：
  描述：

  冬青醇 在 jones reagent 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 costal
  参考文献：
  名称：

  Gastric cytoprotective activity of ilicic aldehyde: Structure–activity relationships

  摘要：

  A series of sesquiterpene compounds possessing both eudesmane and eremophilane skeletons were tested as gastric cyto-protective agents on male Wistar rats. The presence of an alpha,beta-unsaturated aldehyde on the C-7 side chain together with a hydroxyl group at C-4 is the requirement for the observed antiulcerogenic activity. In an attempt to establish new molecular structural requirements for this gastric cytoprotective activity, a structure-activity study was performed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.053
• 作为产物：
  描述：

  4-hydroxy-11(13)-eudesmen-12-oic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 冬青醇
  参考文献：
  名称：

  Sesquiterpenoids and flavonoids from Flourensia oolepis

  摘要：

  DOI：

  10.1016/0031-9422(79)80148-x

文献信息

• Sesquiterpene alcohols from Gonospermum fructicosum
  作者：Antonio G. González、Jaime Bermejo Barrera、Jorge Triana Méndez、Mariana López Sánchez、José L. Eiroa Martínez

  DOI：10.1016/0031-9422(92)83155-r

  日期：1992.5

  Abstract The aerial part of Gonospermum fructicosum yielded three new sesquiterpene alcohols as well as four known compounds. The structures of the new compounds were established as 4α-hydroxy-4β-methyldihydrocostol, 1β-hydroxycostol and 3x-hydroxycostol by spectroscopic and chemical means.

  摘要 Gonospermum fructicosum 地上部分产生了三种新的倍半萜醇和四种已知化合物。通过光谱和化学手段确定了新化合物的结构为4α-羟基-4β-甲基二氢木香酚、1β-羟基木香酚和3x-羟基木香酚。
• 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.