dihydrooenanthotoxin | 20312-71-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dihydrooenanthotoxin
• 英文别名: (8E,10E,14R)-heptadeca-8,10-dien-4,6-diyne-1,14-diol
• CAS: 20312-71-4
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: SZYKBBPFQKNSPD-NNRSTCLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dihydrooenanthotoxin 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 、 4-二甲氨基吡啶 作用下， 以53%的产率得到dihydrooenanthotoxin-1-O-14-O-(S)-MTPA diester
  参考文献：
  名称：

  Polyacetylenes from Sardinian Oenanthe fistulosa: A Molecular Clue to risus sardonicus

  摘要：

  An investigation of Oenanthe fistulosa from Sardinia afforded oenanthotoxin (1a) and dihydrooenanthotoxin (1b) from the roots and the diacetylenic epoxydiol 2 from the seeds. The absolute configuration of 1a and 1b was established as R by the modified Mosher's method, and the structure of 2 by chemical correlation with (+)-(3R,8S)-falcarindiol. Oenanthotoxin (1a) and dihydrooenanthotoxin (1b) were found to potently block GABAergic responses, providing a molecular rationale for the symptoms of poisoning from water-dropwort (Oenanthe crocata) and related plants. These observations bear relevance for a series of historical and ethnopharmacological observations on the identification of the Sardonic herb and the molecular details of the facial muscular contraction caused by its ingestion (risus sardonicus).

  DOI：

  10.1021/np8007717