3-O-isocaproyl-R-carnitine undecyl ester chloride

• 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: 3-O-isocaproyl-R-carnitine undecyl ester chloride
• 英文别名: trimethyl-[(2R)-2-(4-methylpentanoyloxy)-4-oxo-4-undecoxybutyl]azanium;chloride
• 化学式: C₂₄H₄₈NO₄*Cl
• 分子量: 450.102
• InChiKey: WKNPXXBSCRNMTK-VZYDHVRKSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [(R)-3-Carboxy-2-(4-methyl-pentanoyloxy)-propyl]-trimethyl-ammonium; chloride 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 3-O-isocaproyl-R-carnitine undecyl ester chloride
  参考文献：
  名称：

  Formation of micelles and liposomes from carnitine amphiphiles

  摘要：

  Esterification of the carboxy and/or the hydroxy groups of (R)-carnitine (3-hydroxy-4-trimethylammonium butanoate) produces interesting classes of (cationic or zwitterionic) surfactants whose CMC values are in general predictable from their molecular structure. In fact similar relationships between CMC and the number of carbon atoms, C-n, have been found for three classes of such surfactants. However the sensitivity of CMC to C-n for the diesters is considerably lower than that calculated from literature values for the monoesters (either in their cationic or zwitterionic forms). The CMC values for the diesters have been determined by tensiometric, conductimetric and spectrophotometric methods, both in pure water and in 0.154 M NaCl solutions, at 25 degreesC. In particular the tensiometric results provide evidence that double-chain diesters undergo self assembly into structures more complex than simple micelles if the two chains are of comparable length. EPR and electron microscopy experiments show that the aggregates spontaneously formed by these surfactants are a mixture of multilamellar vescicles. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01168-5

文献信息

• Formation of micelles and liposomes from carnitine amphiphiles
  作者：Marta Cipollone、Paolo De Maria、Antonella Fontana、Sara Frascari、Luigi Gobbi、Domenico Spinelli、Mariaornella Tinti

  DOI：10.1016/s0223-5234(00)01168-5

  日期：2000.10

  Esterification of the carboxy and/or the hydroxy groups of (R)-carnitine (3-hydroxy-4-trimethylammonium butanoate) produces interesting classes of (cationic or zwitterionic) surfactants whose CMC values are in general predictable from their molecular structure. In fact similar relationships between CMC and the number of carbon atoms, C-n, have been found for three classes of such surfactants. However the sensitivity of CMC to C-n for the diesters is considerably lower than that calculated from literature values for the monoesters (either in their cationic or zwitterionic forms). The CMC values for the diesters have been determined by tensiometric, conductimetric and spectrophotometric methods, both in pure water and in 0.154 M NaCl solutions, at 25 degreesC. In particular the tensiometric results provide evidence that double-chain diesters undergo self assembly into structures more complex than simple micelles if the two chains are of comparable length. EPR and electron microscopy experiments show that the aggregates spontaneously formed by these surfactants are a mixture of multilamellar vescicles. (C) 2000 Editions scientifiques et medicales Elsevier SAS.