Marrubinsaeure | 564-12-5

• 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: Marrubinsaeure
• 英文别名: 15,16-epoxy-6β,9-dihydroxy-8βH-labda-13(16),14-dien-19-oic acid；15,16-Epoxy-6β,9-dihydroxy-8βH-labda-13(16),14-dien-19-saeure；Marrubic acid；(1S,4aS,5R,6R,8R,8aR)-5-[2-(furan-3-yl)ethyl]-5,8-dihydroxy-1,4a,6-trimethyl-3,4,6,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 564-12-5
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: XNJHGRHUXRWGMG-OBHOOXMTSA-N

物化性质

• LogP：
  3.470 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Marrubinsaeure 在 chromium(VI) oxide 、 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 生成 6,9-dihydroxy-14,15,16-trinor-8βH-labd-6-ene-13,19-dioic acid-13=>9;19=>6-dilactone
  参考文献：
  名称：

  Cocker et al., Journal of the Chemical Society, 1953, p. 2540,2546

  摘要：

  DOI：
• 作为产物：
  描述：

  夏至草素 在 氢氧化钾 作用下， 以 乙二醇乙醚 为溶剂， 反应 15.0h， 以94%的产率得到Marrubinsaeure
  参考文献：
  名称：

  Analgesic potential of marrubiin derivatives, a bioactive diterpene present in Marrubium vulgare (Lamiaceae)

  摘要：

  Marrubiin, a furane labdane diterpene, is the main analgesic compound present in Marrubium vulgare, a medicinal plant used in Brazil and other countries to treat several ailments. Considering its important pharmacological action, as well as its high yield, some structural modifications were performed in order to obtain more active compounds. Success was obtained in reducing the lactonic function, in the formation of marrubiinic acid and two esterified derivatives, which exhibited significant analgesic effect against the writhing test in mice. Marrubiinic acid showed better activity and excellent yield, and its analgesic effect was confirmed in other experimental models of pain in mice, suggesting its possible use as a model to obtain new and potent analgesic agents.

  DOI：

  10.1016/j.farmac.2005.01.003

文献信息

• Hardy et al., Journal of the Chemical Society, 1957, p. 2955,2963
  作者：Hardy et al.

  DOI：——

  日期：——
• 133. Marrubin, the bitter principle of horehound (Marrubium vulgare)
  作者：Alexander Lawson、E. D. Eustice

  DOI：10.1039/jr9390000587

  日期：——
• Ghigi, Gazzetta Chimica Italiana, 1948, vol. 78, p. 856,864
  作者：Ghigi

  DOI：——

  日期：——
• MARRUBIIN.¹
  作者：H. M. Gordin

  DOI：10.1021/ja01944a013

  日期：1908.2
• Ghigi, Gazzetta Chimica Italiana, 1951, vol. 81, p. 336,343
  作者：Ghigi

  DOI：——

  日期：——