(Z,Z)-N-(2,3-dihydroxypropyl)-octadeca-9,12-dienamide | 805251-99-4

• 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: (Z,Z)-N-(2,3-dihydroxypropyl)-octadeca-9,12-dienamide
• 英文别名: N-(2,3-dihydroxypropyl)linoleamide；3-linoleoylamino-1,2-propanediol；(9Z,12Z)-N-(2,3-dihydroxypropyl)octadeca-9,12-dienamide
• CAS: 805251-99-4
• 化学式: C₂₁H₃₉NO₃
• 分子量: 353.546
• InChiKey: NLBFVPKIMGBPGM-HZJYTTRNSA-N

物化性质

• 沸点：
  547.3±50.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z,Z)-N-(2,3-dihydroxypropyl)-octadeca-9,12-dienamide 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 以76%的产率得到N-linoleoyl glycinal
  参考文献：
  名称：

  Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: Synthesis of N-acyl glycinals

  摘要：

  N-Arachidonoyl ethanolamide or anandamide is an endocannabinoid found in most tissues where it acts as an important signaling mediator in a number of physiological and pathophysiological processes. Consequently, intense effort has been focused on understanding all its biosynthetic and metabolic pathways. Herein we report human alcohol dehydrogenase-catalyzed sequential oxidation of anandamide to N-arachidonoyl glycine, a prototypical member of the class of long chain fatty acyl glycines, a new group of lipid mediators with a wide array of physiological effects. We also present a straightforward synthesis for a series of N-acyl glycinals including N-arachidonoyl glycinal, an intermediate in the alcohol dehydrogenase-catalyzed oxidation of anandamide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.087

文献信息

• US7344868B2
  申请人：——

  公开号：US7344868B2

  公开（公告）日：2008-03-18
• Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: Synthesis of N-acyl glycinals
  作者：Halikhedkar Aneetha、David K. O’Dell、Bo Tan、J. Michael Walker、Thomas D. Hurley

  DOI：10.1016/j.bmcl.2008.10.087

  日期：2009.1

  N-Arachidonoyl ethanolamide or anandamide is an endocannabinoid found in most tissues where it acts as an important signaling mediator in a number of physiological and pathophysiological processes. Consequently, intense effort has been focused on understanding all its biosynthetic and metabolic pathways. Herein we report human alcohol dehydrogenase-catalyzed sequential oxidation of anandamide to N-arachidonoyl glycine, a prototypical member of the class of long chain fatty acyl glycines, a new group of lipid mediators with a wide array of physiological effects. We also present a straightforward synthesis for a series of N-acyl glycinals including N-arachidonoyl glycinal, an intermediate in the alcohol dehydrogenase-catalyzed oxidation of anandamide. (C) 2008 Elsevier Ltd. All rights reserved.