(R)-3-carboxy-N,N,N-trimethyl-2-(octanoyloxy)propan-1-ammonium chloride | 54377-02-5

• 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: (R)-3-carboxy-N,N,N-trimethyl-2-(octanoyloxy)propan-1-ammonium chloride
• 英文别名: O-octanoyl-L-carnitine hydrochloride；octanoyl-L-carnitine hydrochloride；(3R)-3-octanoyloxy-4-(trimethylazaniumyl)butanoate;hydrochloride
• CAS: 54377-02-5
• 化学式: C₁₅H₃₀NO₄*Cl
• 分子量: 323.861
• InChiKey: MYMFUYYXIJGKKU-BTQNPOSSSA-N

物化性质

• 溶解度：
  DMF：20mg/mL； DMSO：10mg/mL；乙醇：20mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -0.56
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 储存条件：
  -20°C，密闭保存，置于干燥处

制备方法与用途

L-八酰基肉碱盐酸盐是一种血浆中的代谢产物，同时也是八酰基肉碱的生理活性形式。L-八酰基肉碱盐酸盐可应用于乳腺癌的研究中。

反应信息

• 作为反应物：
  描述：

  (R)-3-carboxy-N,N,N-trimethyl-2-(octanoyloxy)propan-1-ammonium chloride 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  左旋肉碱盐酸盐 、 辛酰氯 在 三氟乙酸 作用下， 反应 20.0h， 生成 (R)-3-carboxy-N,N,N-trimethyl-2-(octanoyloxy)propan-1-ammonium chloride
  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

• Process for the production of a fatty acid/carnitine derivative
  申请人：Lonza Ltd.

  公开号：EP2216321A1

  公开（公告）日：2010-08-11

  The present invention discloses a process for the production of a fatty acid/L-carnitine.HCl derivative, whereby the educts are reacted in the presence of mono-chloroacetic acid.

  本发明揭示了一种用于生产脂肪酸/L-肉碱.HCl衍生物的过程，其中在单氯乙酸的存在下，反应底物。
• 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.
• PROCESS FOR THE PRODUCTION OF A FATTY ACID/L-CARNITINE DERIVATIVE
  申请人：Lonza Ltd

  公开号：EP2393774A1

  公开（公告）日：2011-12-14
• PROCESS FOR THE PRODUCTION OF A FATTY ACID/CARNITINE DERIVATIVE
  申请人：Smida Donya

  公开号：US20110295026A1

  公开（公告）日：2011-12-01

  The present invention discloses a process for the production of a fatty acid/L-carnitine derivative, whereby the educts are reacted in the presence of monochloroacetic acid.
• US8614343B2
  申请人：——

  公开号：US8614343B2

  公开（公告）日：2013-12-24