caryophyllene-5α,(11R)-15-diol | 1260000-03-0

• 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
• 英文名称: caryophyllene-5α,(11R)-15-diol
• CAS: 1260000-03-0
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: LWDUKJKEQNFYDO-ARILJUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  caryophylla-4(12),8(13)-dien-5α-ol 在 Macrophomina phaseolina KUCC 730 作用下， 以 丙酮 为溶剂， 反应 144.0h， 以47.6 mg的产率得到4β-methoxycaryophyllene-5α,(11R)-15-diol
  参考文献：
  名称：

  Microbial transformation of 5α-hydroxycaryophylla-4(12), 8(13)-diene with Macrophomina phaseolina

  摘要：

  Biotransformation of 5 alpha-hydroxycaryophylla-4(12), 8(13)-diene (1) by the fungus Macrophomina phaseolina resulted into regioselective oxidation at C-4(12) exocyclic double bond and C-11 gem-methyl groups, leading to the formation of three new metabolites, 4 beta-methoxycaryophyllene-5 alpha, (11S)-14-diol (2), 4 beta-methoxycaryophyllene-5 alpha, (1 1 R)-15-diol (3), and caryophyllene-5 alpha, (11R)-15-diol (4). The structures of metabolites were deduced by spectroscopic and single-crystal X-ray diffraction analysis. Compounds 1-4 were evaluated for in vitro antimalarial activity, where compound 2 exhibited an IC50 value of 0.72 +/- 0.17 mu g/ml (standard chloroquine diphosphate, IC50 = 0.025 +/- 0.01 mu g/ml). (C) 2010 Published by Elsevier B.V.

  DOI：

  10.1016/j.molcatb.2010.04.011