N-palmitoyl,O-octanoylethanolamine | 1253906-56-7

• 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: N-palmitoyl,O-octanoylethanolamine
• 英文别名: 2-(Hexadecanoylamino)ethyl octanoate；2-(hexadecanoylamino)ethyl octanoate
• CAS: 1253906-56-7
• 化学式: C₂₆H₅₁NO₃
• 分子量: 425.696
• InChiKey: AMNCTJBEFZKUDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  30
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  十六酰胺乙醇 、 辛酰氯 以 二氯甲烷 为溶剂， 生成 N-palmitoyl,O-octanoylethanolamine
  参考文献：
  名称：

  Polymorphism in ‘L’ shaped lipids: structure of N-, O-diacylethanolamines with mixed acyl chains

  摘要：

  Although solid state polymorphism in lipids has been established by spectroscopic and calorimetric studies long ago, only in a few cases crystal structures of different polymorphs of the same compound have been reported, possibly due to difficulties in obtaining high quality single crystals of individual polymorphs. Recent studies show that N-, O-diacylethanolamines (DAEs) can be derived by the O-acylation of the stress-related lipids. the N-acylethanolamines under physiological conditions. In this study, two DAEs with mixed acyl chains, namely N-palmitoyl, O-octanoylethanolamine and N-palmitoyl, O-decanoylethanolamine have been synthesized and their three-dimensional structures were determined. Both the compounds were found to adopt 'L' shaped structures and exist in two polymorphic forms, alpha and beta. In the alpha form a mixed-type chain packing has been observed whereas in the beta form the chain packing is symmetric. Similar polymorphic forms are likely to exist in other 'L' shaped lipids such as 1,3-diacylglycerols and ceramides, where polymorphism has been detected earlier, but three-dimensional structures-which can give precise information about the packing at atomic resolution have not been reported. (C) 2009 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2009.08.004

文献信息

• Nonclassical Odd–even Alternation in Mixed-Chain Diacylethanolamines: Implications of Polymorphism
  作者：Pradip K. Tarafdar、S. Thirupathi Reddy、Musti J. Swamy

  DOI：10.1021/cg200698t

  日期：2012.3.7

  N,O-Diacylethanolamines (DAEs), derived by the O-acylation of bioactive N-acylethanolamines (NAEs), are most likely present in biological membranes. In the present study, a homologous series of mixed chain DAEs with an N-palmitoyl chain and varying O-acyl chains (n = 6-16) have been synthesized and characterized. Differential scanning calorimetry (DSC) studies revealed a nonclassical type of odd-even alternation in the enthalpy and entropy of melting, with the odd-even effect becoming more prominent with increase in the O-acyl chain length. This was rationalized by analyzing the 3-dimensional structures of several DAEs. In most cases, two types of packing polymorphs (alpha and beta) were observed; while the alpha polymorph is characterized by a mixed type of chain packing, in the beta polymorph the chain packing is symmetric. Analysis of the crystal structures revealed that the odd-even effect is manifested through differences in the packing of acyl chains, with the packing being closer when both chains are even. A possible role of polymorphism in the odd-even effect has also been considered, and it was suggested that the nonclassical behavior observed in the alternation could be attributed to the presence of different fractions of the alpha and beta forms in the bulk mixture. Similar nonclassical odd-even effects and polymorphism may exist in other mixed chain systems, which adopt an "L" shape.
• Polymorphism in ‘L’ shaped lipids: structure of N-, O-diacylethanolamines with mixed acyl chains
  作者：Pradip K. Tarafdar、Musti J. Swamy

  DOI：10.1016/j.chemphyslip.2009.08.004

  日期：2009.11

  Although solid state polymorphism in lipids has been established by spectroscopic and calorimetric studies long ago, only in a few cases crystal structures of different polymorphs of the same compound have been reported, possibly due to difficulties in obtaining high quality single crystals of individual polymorphs. Recent studies show that N-, O-diacylethanolamines (DAEs) can be derived by the O-acylation of the stress-related lipids. the N-acylethanolamines under physiological conditions. In this study, two DAEs with mixed acyl chains, namely N-palmitoyl, O-octanoylethanolamine and N-palmitoyl, O-decanoylethanolamine have been synthesized and their three-dimensional structures were determined. Both the compounds were found to adopt 'L' shaped structures and exist in two polymorphic forms, alpha and beta. In the alpha form a mixed-type chain packing has been observed whereas in the beta form the chain packing is symmetric. Similar polymorphic forms are likely to exist in other 'L' shaped lipids such as 1,3-diacylglycerols and ceramides, where polymorphism has been detected earlier, but three-dimensional structures-which can give precise information about the packing at atomic resolution have not been reported. (C) 2009 Elsevier Ireland Ltd. All rights reserved.