N-(2-Lauroyl-oxyethyl)-lauramid | 5168-42-3

• 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-(2-Lauroyl-oxyethyl)-lauramid
• 英文别名: N,O-dilauroylethanolamine；DLEA；2-(Dodecanoylamino)ethyl dodecanoate
• CAS: 5168-42-3
• 化学式: C₂₆H₅₁NO₃
• 分子量: 425.696
• InChiKey: KCFQCBCAMPUPQK-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：

  月桂酰氯 、 C.I.酸性橙108 以 二氯甲烷 为溶剂， 生成 N-(2-Lauroyl-oxyethyl)-lauramid
  参考文献：
  名称：

  Synthesis, calorimetric studies, and crystal structures of N, O-diacylethanolamines with matched chains

  摘要：

  Recent studies show that N-, O-diacylethanolamines (DAEs) can be derived by the O-acylation of N-acylethanolamines (NAEs) under physiological conditions. Because the content of NAEs in a variety of organisms increases in response to stress, it is likely that DAEs may also be present in biomembranes. In view of this, a homologous series of DAEs with matched acyl chains (n = 10-20) have been synthesized and characterized. Transition enthalpies and entropies obtained from differential scanning calorimetry show that dry DAEs with even and odd acyl chains independently exhibit linear dependence on the chainlength. Linear least-squares analyses yielded incremental values contributed by each methylene group to the transition enthalpy and entropy and the corresponding end contributions. N-, O-Didecanoylethanolamine (DDEA), N-, O-dilauroylethanolamine (DLEA), and N-, O-dimyristoylethanolamine (DMEA) crystallized in the orthorhombic space group Pbc(21) with four symmetry-related molecules in the unit cell. Single-crystal X-ray diffraction studies show that DDEA, DLEA, and DMEA are isostructural and adopt an L-shaped structure with the N- acyl chain and the central ethanolamine moiety being essentially identical to the structure of N- acylethanolamines, whereas the O-acyl chain is linear with alltrans conformation. In all three DAEs, the lipid molecules are organized in a bilayer fashion wherein the N-acyl and O-acyl chains from adjacent layers oppose each other. Kamlekar, R. K., P. K. Tarafdar, and M. J. Swamy. Synthesis, calorimetric studies, and crystal structures of N, O-diacylethanolamines with matched chains. J. Lipid Res. 2010. 51. 42-52.

  DOI：

  10.1194/jlr.m900105-jlr200

文献信息

• US5602208A
  申请人：——

  公开号：US5602208A

  公开（公告）日：1997-02-11
• Synthesis, calorimetric studies, and crystal structures of N, O-diacylethanolamines with matched chains
  作者：Ravi Kanth Kamlekar、Pradip K. Tarafdar、Musti J. Swamy

  DOI：10.1194/jlr.m900105-jlr200

  日期：2010.1

  Recent studies show that N-, O-diacylethanolamines (DAEs) can be derived by the O-acylation of N-acylethanolamines (NAEs) under physiological conditions. Because the content of NAEs in a variety of organisms increases in response to stress, it is likely that DAEs may also be present in biomembranes. In view of this, a homologous series of DAEs with matched acyl chains (n = 10-20) have been synthesized and characterized. Transition enthalpies and entropies obtained from differential scanning calorimetry show that dry DAEs with even and odd acyl chains independently exhibit linear dependence on the chainlength. Linear least-squares analyses yielded incremental values contributed by each methylene group to the transition enthalpy and entropy and the corresponding end contributions. N-, O-Didecanoylethanolamine (DDEA), N-, O-dilauroylethanolamine (DLEA), and N-, O-dimyristoylethanolamine (DMEA) crystallized in the orthorhombic space group Pbc(21) with four symmetry-related molecules in the unit cell. Single-crystal X-ray diffraction studies show that DDEA, DLEA, and DMEA are isostructural and adopt an L-shaped structure with the N- acyl chain and the central ethanolamine moiety being essentially identical to the structure of N- acylethanolamines, whereas the O-acyl chain is linear with alltrans conformation. In all three DAEs, the lipid molecules are organized in a bilayer fashion wherein the N-acyl and O-acyl chains from adjacent layers oppose each other. Kamlekar, R. K., P. K. Tarafdar, and M. J. Swamy. Synthesis, calorimetric studies, and crystal structures of N, O-diacylethanolamines with matched chains. J. Lipid Res. 2010. 51. 42-52.