ribenol | 51196-77-1

• 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: ribenol
• 英文别名: ent-3β-hydroxy-13-epi-manoyl oxide；(3R,4aS,6aS,8R,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-8-ol
• CAS: 51196-77-1；57457-19-9；74311-13-0；74523-81-2；76250-25-4；77943-71-6；113566-87-3；42895-91-0
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: JJZSRKRSWWPWCJ-LZHQGQFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ribenol 在 jones' reagent 、 Curvularia lunata 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 ent-3α-acetoxy-11β-hydroxy-13-epi-manoyl oxide
  参考文献：
  名称：

  Chemical-microbiological synthesis of ent-13-epi-manoyl oxides with biological activities

  摘要：

  The biotransformation of ent-13-epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6 beta-hydroxy, ent-1 alpha-hydroxy, ent-11 beta-hydroxy and Delta(1)-derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6 beta) or C-11 tent-11 beta). The ent-6 beta-hydroxy and Delta(1)-derivatives inhibited growth of the pathogenic protozoa, Leishmania donovani. The biotransformation of ent-12 alpha-acetoxy-3 beta-hydroxy-13-epi-manoyl oxide and ent-3 beta-acetoxy-12-oxo-13-epi-manoyl oxide gave the ent-6 beta-hydroxyl derivatives. The incubation of ent-3 beta-acetoxy-12 beta-dihydroxy-13-epi-manoyl oxide gave ent-3 beta,12 beta-dihydroxy-13-epi-manoyl oxide and ent-3 beta,6 beta,12 beta-trihydroxy-13-epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.

  DOI：

  10.1016/s0031-9422(00)90350-9

文献信息

• FRAGA, BRAULIO M.;GONZALEZ, PEDRO;GUILLERMO, RICARDO;HERNANDEZ, MELCHOR G+, PHYTOCHEMISTRY, 28,(1989) N, C. 1851-1854
  作者：FRAGA, BRAULIO M.、GONZALEZ, PEDRO、GUILLERMO, RICARDO、HERNANDEZ, MELCHOR G+

  DOI：——

  日期：——
• Chemical-microbiological synthesis of ent-13-epi-manoyl oxides with biological activities
  作者：Andrés García-Granados、M Belinda Jiménez、Antonio Martínez、Andrés Parra、Francisco Rivas、José María Arias

  DOI：10.1016/s0031-9422(00)90350-9

  日期：1994.11

  The biotransformation of ent-13-epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6 beta-hydroxy, ent-1 alpha-hydroxy, ent-11 beta-hydroxy and Delta(1)-derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6 beta) or C-11 tent-11 beta). The ent-6 beta-hydroxy and Delta(1)-derivatives inhibited growth of the pathogenic protozoa, Leishmania donovani. The biotransformation of ent-12 alpha-acetoxy-3 beta-hydroxy-13-epi-manoyl oxide and ent-3 beta-acetoxy-12-oxo-13-epi-manoyl oxide gave the ent-6 beta-hydroxyl derivatives. The incubation of ent-3 beta-acetoxy-12 beta-dihydroxy-13-epi-manoyl oxide gave ent-3 beta,12 beta-dihydroxy-13-epi-manoyl oxide and ent-3 beta,6 beta,12 beta-trihydroxy-13-epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.