all-trans N-arachidonoylethanolamine | 1072878-74-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: all-trans N-arachidonoylethanolamine
• 英文别名: all-trans anandamide；(5E,8E,11E,14E)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
• CAS: 1072878-74-0
• 化学式: C₂₂H₃₇NO₂
• 分子量: 347.541
• InChiKey: LGEQQWMQCRIYKG-CGRWFSSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  全反式花生四烯酸甲酯 、 C.I.酸性橙108 在 potassium cyanide 作用下， 以 甲醇 为溶剂， 以70%的产率得到all-trans N-arachidonoylethanolamine
  参考文献：
  名称：

  Synthesis of all-trans anandamide: A substrate for fatty acid amide hydrolase with dual effects on rabbit platelet activation

  摘要：

  Anandamide (AEA) presents the four double bonds in the cis configuration, deriving from the arachidonic acid moiety. In the context of an antisense strategy based on the double bond configuration, all-trans AEA (t-AEA) was synthesized in high yield starting from all-trans methyl arachidonate and ethanolamine in the presence of KCN. t-AEA was assayed on rabbit platelet aggregation, obtaining effect only at high concentrations (> 10 (4) M) after an also concentration-dependent lag phase. At lower concentrations it inhibited PAF-induced rabbit platelet aggregation with an IC50 = 4.6 x 10 (6) M. In contrast to anandamide, the activation of platelets was not due to the conversion of t-AEA to trans arachidonic acid, as ascertained by negative results with FAAH inhibitors. However, t-AEA was found to be a substrate for fatty acid amide hydrolase (FAAH), the enzyme that cleaves anandamide and regulates in vivo the magnitude and duration of the signaling induced by this lipid messenger. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.054

文献信息

• Synthesis of all-trans anandamide: A substrate for fatty acid amide hydrolase with dual effects on rabbit platelet activation
  作者：Carla Ferreri、Dimitris Anagnostopoulos、Ioannis N. Lykakis、Chryssostomos Chatgilialoglu、Athanassia Siafaka-Kapadai

  DOI：10.1016/j.bmc.2008.08.054

  日期：2008.9

  Anandamide (AEA) presents the four double bonds in the cis configuration, deriving from the arachidonic acid moiety. In the context of an antisense strategy based on the double bond configuration, all-trans AEA (t-AEA) was synthesized in high yield starting from all-trans methyl arachidonate and ethanolamine in the presence of KCN. t-AEA was assayed on rabbit platelet aggregation, obtaining effect only at high concentrations (> 10 (4) M) after an also concentration-dependent lag phase. At lower concentrations it inhibited PAF-induced rabbit platelet aggregation with an IC50 = 4.6 x 10 (6) M. In contrast to anandamide, the activation of platelets was not due to the conversion of t-AEA to trans arachidonic acid, as ascertained by negative results with FAAH inhibitors. However, t-AEA was found to be a substrate for fatty acid amide hydrolase (FAAH), the enzyme that cleaves anandamide and regulates in vivo the magnitude and duration of the signaling induced by this lipid messenger. (C) 2008 Elsevier Ltd. All rights reserved.