oenanthotoxin-1-O-14-O-(R)-MTPA diester | 1135133-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: oenanthotoxin-1-O-14-O-(R)-MTPA diester
• 英文别名: [(2E,8E,10E,14R)-14-[(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxyheptadeca-2,8,10-trien-4,6-diynyl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1135133-75-3
• 化学式: C₃₇H₃₆F₆O₆
• 分子量: 690.68
• InChiKey: XQCNBXAGZPPWJE-MOGPLXQVSA-N

物化性质

• 沸点：
  731.9±60.0 °C(predicted)
• 密度：
  1.223±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  水芹毒素 、 甲氧基-三氟甲基苯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以53%的产率得到oenanthotoxin-1-O-14-O-(R)-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

文献信息

• Polyacetylenes from Sardinian <i>Oenanthe fistulosa</i>: A Molecular Clue to <i>risus sardonicus</i>
  作者：Giovanni Appendino、Federica Pollastro、Luisella Verotta、Mauro Ballero、Adriana Romano、Paulina Wyrembek、Katarzyna Szczuraszek、Jerzy W. Mozrzymas、Orazio Taglialatela-Scafati

  DOI：10.1021/np8007717

  日期：2009.5.22

  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).