清艾菊素A | 24959-84-0

• 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: 清艾菊素A
• 英文名称: canin
• 英文别名: (1R,2R,5S,9S,10S,11S,13R,14S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.01,14.05,9.011,13]pentadecan-7-one
• CAS: 24959-84-0
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: KXLUWEYBZBGJRZ-POEOZHCLSA-N

物化性质

• 熔点：
  245-246 °C
• 沸点：
  487.2±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S,2R,5S,9S,10S,11S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,13-trioxatetracyclo[9.2.2.01,10.05,9]pentadec-14-en-7-one 生成 清艾菊素A
  参考文献：
  名称：

  BEGLEY, MICHAEL J.;HEWLETT, MARTIN J.;KNIGHT, DAVID W., PHYTOCHEMISTRY, 28,(1989) N 3, C. 940-943

  摘要：

  DOI：

文献信息

• Sesquiterpene lactones from feverfew, Tanacetum parthenium: isolation, structural revision, activity against human blood platelet function and implications for migraine therapy
  作者：Martin J. Hewlett、Michael J. Begley、W. Antoinette Groenewegen、Stan Heptinstall、David W. Knight、Jane May、Umit Salan、Dane Toplis

  DOI：10.1039/p19960001979

  日期：——

  The structures of two series of sesquiterpene lactones (the ‘α’-series 11, 12 and 16 and the ‘β’-series 15, 17 and 18) present in the herb feverfew have been revised in the light of both X-ray analysis and chemical correlations. A biosynthetic pathway is proposed, involving a Diels–Alder type addition of oxygen followed by two contrasting rearrangements, starting from a common intermediate, the cyclopentadiene 19, which has not been identified in feverfew extracts but which is related to a recently isolated structure. The activity of some of these metabolites as well as of the major sesquiterpene lactone present in feverfew, parthenolide 2, and some simple synthetic models as inhibitors of human blood platelet function has been determined. The possible relevance of this effect to migraine prophylaxis by feverfew is briefly discussed.

  根据 X 射线分析和化学相关性，对发热草中的两个倍半萜内酯系列（"α "系列 11、12 和 16 以及 "β "系列 15、17 和 18）的结构进行了修订。提出了一种生物合成途径，其中包括一个 Diels-Alder 型氧气加成过程，然后是两个截然不同的重排，从一个共同的中间体环戊二烯 19 开始，该中间体尚未在发热草提取物中发现，但与最近分离出的一个结构有关。我们已经确定了其中一些代谢物以及发热草中的主要倍半萜内酯 Parthenolide 2 和一些简单合成模型作为人体血小板功能抑制剂的活性。本文简要讨论了这种作用与发热草预防偏头痛的可能相关性。
• Revised structures for guaianolide α-methylenebutyro-lactones from feverfew
  作者：Michael J. Begley、Martin J. Hewlett、David W. Knight

  DOI：10.1016/0031-9422(89)80150-5

  日期：1989.1

  Abstract The structures of two series of guaianolides present in feverfew, Tanacetum parthenium , are established as tanaparthin-α-peroxide, canin and seco -tanapartholide-A [major group] and the corresponding ‘β’-series [β-peroxide, artecanin and the seco -B derivative] using a combination of spectroscopic and X-ray crystallographic analyses and chemical transformations.

  摘要 存在于小白菊中的两个系列愈创木酚内酯的结构被确定为 tanaparthin-α-peroxide, canin 和 seco-tanapartholide-A [major group] 以及相应的'β'-系列 [β-peroxide, artecanin and seco-B衍生物]使用光谱和X射线晶体学分析和化学转化的组合。
• BEGLEY, MICHAEL J.;HEWLETT, MARTIN J.;KNIGHT, DAVID W., PHYTOCHEMISTRY, 28,(1989) N 3, C. 940-943
  作者：BEGLEY, MICHAEL J.、HEWLETT, MARTIN J.、KNIGHT, DAVID W.

  DOI：——

  日期：——