5-(F-octyl)-pentanoyl carnitine | 142674-36-0

• 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: 5-(F-octyl)-pentanoyl carnitine
• 英文别名: 3-(6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heptadecafluorotridecanoyloxy)-4-(trimethylazaniumyl)butanoate
• CAS: 142674-36-0
• 化学式: C₂₀H₂₂F₁₇NO₄
• 分子量: 663.372
• InChiKey: REJPMZDEYKRFJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  heptadecafluorotridecanoic acid 在 氯化亚砜 作用下， 以 三氟乙酸 为溶剂， 反应 6.0h， 生成 5-(F-octyl)-pentanoyl carnitine
  参考文献：
  名称：

  Synthesis and preliminary evaluation of perfluoroalkylacyl carnitines as surfactants for biomedical use

  摘要：

  A series of acyl carnitines, 4 of which bearing a terminal perfluoroalkyl fragment, was obtained from carnitine in one step in a high grade of purity in yields ranging from 44-81%. The F-alkyl derivatives display high solubilities in water, strong surface activity and a significant emulsifying power towards fluorocarbons in water. In spite of their strong surface activity, all the biocompatibility tests performed (in vitro toxicity on Namalva cells cultures, hemolysis on human red blood cells, and iv injections in mice) indicate a significantly better biological tolerance than their hydrocarbon analogs, provided the F-alkyl moiety is larger than the alkyl moiety in the hydrophobic tail.

  DOI：

  10.1016/0223-5234(91)90138-d

文献信息

• Synthesis and preliminary evaluation of perfluoroalkylacyl carnitines as surfactants for biomedical use
  作者：JB Nivet、M Le Blanc、JG Riess

  DOI：10.1016/0223-5234(91)90138-d

  日期：1991.12

  A series of acyl carnitines, 4 of which bearing a terminal perfluoroalkyl fragment, was obtained from carnitine in one step in a high grade of purity in yields ranging from 44-81%. The F-alkyl derivatives display high solubilities in water, strong surface activity and a significant emulsifying power towards fluorocarbons in water. In spite of their strong surface activity, all the biocompatibility tests performed (in vitro toxicity on Namalva cells cultures, hemolysis on human red blood cells, and iv injections in mice) indicate a significantly better biological tolerance than their hydrocarbon analogs, provided the F-alkyl moiety is larger than the alkyl moiety in the hydrophobic tail.