异戊酰基L-肉碱氯化物 | 139144-12-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 异戊酰基L-肉碱氯化物
• 英文名称: (R)-3-carboxy-N,N,N-trimethyl-2-(3-methylbutanoyloxy)propan-1-ammonium chloride
• 英文别名: (3R)-3-(3-methylbutanoyloxy)-4-(trimethylazaniumyl)butanoate;hydrochloride
• CAS: 139144-12-0
• 化学式: C₁₂H₂₄NO₄*Cl
• 分子量: 281.78
• InChiKey: HWDFIOSIRGUUSM-HNCPQSOCSA-N

物化性质

• 熔点：
  >160°C (dec.)
• 溶解度：
  轻微溶于甲醇、加热微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -1.87
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

制备方法与用途

氯化异戊酰肉碱是L-亮氨酸分解代谢的产物，它是人类中性粒细胞钙依赖性蛋白酶（钙蛋白酶）的有效激活剂。

反应信息

• 作为反应物：
  描述：

  异戊酰基L-肉碱氯化物 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 3-O-isovaleryl-R-carnitine tridecyl 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
• 作为产物：
  描述：

  左旋肉碱盐酸盐 、 异戊酰氯 在 三氟乙酸 作用下， 反应 20.0h， 生成 异戊酰基L-肉碱氯化物
  参考文献：
  名称：

  Synthesis of Carnitine Benzyl Esters as Prodrugs

  摘要：

  在左旋肉碱中引入 C-2酰基和苄基酯后，产生了一系列左旋肉碱苄基酯原药，它们的脂溶性、稳定性和生物利用度都得到了改善。

  DOI：

  10.3184/030823408x324689

文献信息

• JPH0597785A
  申请人：——

  公开号：JPH0597785A

  公开（公告）日：1993-04-20
• Synthesis of Carnitine Benzyl Esters as Prodrugs
  作者：Xiao-wei Gong、Jin-pei Li、Ji-feng Wu、Li Xun、Hai-min Zhai、Bo Feng、Wen-fang Xu、Wei Tang

  DOI：10.3184/030823408x324689

  日期：2008.6

  The introduction of C-2 acyl groups and a benzyl ester onto L-carnitine generated a series of carnitine benzyl esters as prodrug with improved liposolubility, stability and bioavailability.

  在左旋肉碱中引入 C-2酰基和苄基酯后，产生了一系列左旋肉碱苄基酯原药，它们的脂溶性、稳定性和生物利用度都得到了改善。
• 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.