20-deoxocarnosol | 94529-97-2

• 物质功能分类: 天然产物 - 萜类
• 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: 20-deoxocarnosol
• 英文别名: 20-deoxycarnosol；20-deoxo-carnosol；(1R,8S,10S)-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-triene-3,4-diol
• CAS: 94529-97-2
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: XCVWKCGUFCXDHN-AUSJPIAWSA-N

物化性质

• 熔点：
  180-183℃
• 沸点：
  463.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 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)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭。

制备方法与用途

20-去氧熊果酸（化合物7）是一种有效的抗癌物质，在鼠尾草的根部可以找到。研究显示，20-去氧熊果酸在癌细胞中具有细胞毒作用。

反应信息

• 作为反应物：
  描述：

  20-deoxocarnosol 在 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (1R,8S,10S)-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2(7),5-diene-3,4-dione
  参考文献：
  名称：

  An abietane diterpene from the labiate Coleus barbatus

  摘要：

  DOI：

  10.1016/s0031-9422(00)83467-6
• 作为产物：
  描述：

  鼠尾草酸 在 lithium aluminium tetrahydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 5.25h， 生成 20-deoxocarnosol
  参考文献：
  名称：

  Cytotoxicity of abietane diterpenoids from Perovskia abrotanoides and of their semisynthetic analogues

  摘要：

  Seven known abietane diterpenoids and 11-O- and 12-O-acetylcarnosic acids were isolated from a methanol extract of Perovskia abrotanoides (Labiatae). Structure and cytotoxic activity relationships (SARs) of the natural and semisynthetic analogues of the presently isolated abietane diterpenoids were studied by using P388 murine leukemia cells. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.047

文献信息

• DIETARY AND PHARMACEUTICAL COMPOSITIONS COMPRISING A SAGE EXTRACT CONTAINING A MIXTURE OF TRICYCLIC DITERPENES AND THEIR DERIVATIVES AND THEIR USES
  申请人：Fowler Ann

  公开号：US20100317728A1

  公开（公告）日：2010-12-16

  The present invention refers to a sage extract containing a mixture of tricyclic diterpene (derivative)s of the formulae I to III, preferably to a sage extract containing a mixture of tricyclic diterpene (derivative)s of the formulae I to IV, more preferably to a sage extract containing a mixture of tricyclic diterpene (derivative)s of the formulae I to V, for use as medicaments for the treatment of a disorder connected to reduced neurotransmission, as well as to dietary and pharmaceutical compositions and their uses.
• Cytotoxicity of abietane diterpenoids from Perovskia abrotanoides and of their semisynthetic analogues
  作者：Yutaka Aoyagi、Yoshinao Takahashi、Yudai Satake、Koichi Takeya、Ritsuo Aiyama、Takeshi Matsuzaki、Shusuke Hashimoto、Teruo Kurihara

  DOI：10.1016/j.bmc.2006.03.047

  日期：2006.8

  Seven known abietane diterpenoids and 11-O- and 12-O-acetylcarnosic acids were isolated from a methanol extract of Perovskia abrotanoides (Labiatae). Structure and cytotoxic activity relationships (SARs) of the natural and semisynthetic analogues of the presently isolated abietane diterpenoids were studied by using P388 murine leukemia cells. (c) 2006 Elsevier Ltd. All rights reserved.
• An abietane diterpene from the labiate Coleus barbatus
  作者：Alphonse Kelecom

  DOI：10.1016/s0031-9422(00)83467-6

  日期：1984.1