N-棕榈酰鞘磷脂 | 1040364-26-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 中文名称: N-棕榈酰鞘磷脂
• 英文名称: N-palmitoyl sphingomyelin
• CAS: 1040364-26-8
• 化学式: C₄₀H₈₁N₂O₅P
• 分子量: 701.067
• InChiKey: ZCZBHDNCTBDAJO-NBZFQWPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.24
• 重原子数：
  48.0
• 可旋转键数：
  36.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  98.69
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(trimethylammonio)ethyl ((3S,4R,E)-4-(((benzyloxy)carbonyl)oxy)-3-palmitamidononadec-5-en-1-yl)phosphonate 在 甲醇 、 氢氧化钾 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以76%的产率得到N-棕榈酰鞘磷脂
  参考文献：
  名称：

  通过通用的烯烃交叉复分解方法合成鞘磷脂亚甲基，氮杂和硫类似物

  摘要：

  通过使用1-十五碳烯与氨基之间的烯烃交叉复分解规程成功地完成了光学均质的鞘磷脂类似物的合成，该类似物具有CH 2，NH和S，而不是将磷酸胆碱头基连接至鞘氨醇主链的磷酸氧具有用于构建磷酸胆碱部分的合适结构单元或官能团的醇部分。此外，还合成了荧光标记的鞘磷脂亚甲基类似物。

  DOI：

  10.1016/j.tet.2008.10.018

文献信息

• Structural role of mismatched C–C bonds in a series of d-erythro-sphingomyelins as studied by DSC and electron microscopy
  作者：Michiko Kodama、Yuko Kawasaki

  DOI：10.1016/j.chemphyslip.2010.03.003

  日期：2010.6

  A series of D-erythro (2S, 3R) sphingomyelins (SMs) whose acyl chain was 16, 18, 20, 22, and 24 carbons long, respectively, was synthesized by the acylation of D-erythro-sphingosylphosphorylcholine. For all the SM dispersions, reversible and reproducible thermal behavior was observed to show the gel-to-gel and the main gel-to-liquid crystal phase transition in heating scan. The main transition enthalpy (Delta H-M) decreased linearly with increasing acyl chain length. The vesicular structures were observed for all the gel phases at temperatures just below the main transition, but the mean diameter of these vesicles changed markedly from similar to 1.5 to 100 nm with increasing acyl chain length. On this basis, the decrease in Delta H-M with increasing acyl chain length was discussed from the viewpoint of the effect of the mismatched C-C bonds in the acyl chain on the van der Waals attractive force between the matched acyl chain segment and the sphingoshine chain of the gel phase at temperatures just below the main transition. (C) 2010 Elsevier Ireland Ltd. All rights reserved.