N,O-dipalmitoylethanolamine | 55349-67-2

• 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,O-dipalmitoylethanolamine
• 英文别名: DPEA；2-(Hexadecanoylamino)ethyl hexadecanoate；2-(hexadecanoylamino)ethyl hexadecanoate
• CAS: 55349-67-2
• 化学式: C₃₄H₆₇NO₃
• 分子量: 537.911
• InChiKey: LILKVUWDDOPGCO-UHFFFAOYSA-N

物化性质

• 沸点：
  638.1±38.0 °C(Predicted)
• 密度：
  0.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  38
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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 、 棕榈酰氯 以 二氯甲烷 为溶剂， 生成 N,O-dipalmitoylethanolamine
  参考文献：
  名称：

  Nonclassical Odd–even Alternation in Mixed-Chain Diacylethanolamines: Implications of Polymorphism

  摘要：

  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.

  DOI：

  10.1021/cg200698t

文献信息

• 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.
• METHODS FOR PROVIDING HIGHLY PURE PALMITOYLETHANOLAMIDE (PEA), PURE PEA PREPARATIONS, AND USES THEREOF
  申请人：Innexus Nutraceuticals B.V.

  公开号：EP3687971A1

  公开（公告）日：2020-08-05
• METHODS FOR PROVIDING HIGHLY PURE PALMITOYLETHANOLAMIDE (PEA)
  申请人：Innexus Nutraceuticals B.V.

  公开号：EP3687971B1

  公开（公告）日：2022-02-23
• [EN] METHODS FOR PROVIDING HIGHLY PURE PALMITOYLETHANOLAMIDE (PEA), PURE PEA PREPARATIONS, AND USES THEREOF<br/>[FR] PROCÉDÉS PERMETTANT DE FOURNIR UNE PALMITOYLÉTHANOLAMIDE (PEA) TRÈS PURE, PRÉPARATIONS DE PEA PURES ET UTILISATIONS ASSOCIÉES
  申请人：INNEXUS NUTRACEUTICALS B V

  公开号：WO2019066644A1

  公开（公告）日：2019-04-04

  The invention relates to the field of medicinal chemistry, more in particular to methods for providing highly pure, pharmaceutical grade synthetic Palmitoylethanolamine (PEA), to pure PEA preparations obtainable thereby, and the uses thereof. Provided is a method for providing pure PEA, comprising the steps of (i) heating a suspension of crude PEA in a solvent mixture in the presence of a base catalyst having a pKA of at least 13 to reflux, thereby allowing the formation of crystalline PEA; and (ii) isolating said crystalline PEA.
• 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.