异丁酰基L-肉碱氯化物

• 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: 异丁酰基L-肉碱氯化物
• 英文名称: (-)-O-Isobutyryl-carnitin
• 英文别名: (3R)-3-(2-methylpropanoyloxy)-4-(trimethylazaniumyl)butanoate;hydrochloride
• 化学式: C₁₁H₂₂NO₄*Cl
• 分子量: 267.753
• InChiKey: FWUACOYFRJEMMP-SBSPUUFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.26
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异丁酰基L-肉碱氯化物 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 ((R)-3-Chlorocarbonyl-2-isobutyryloxy-propyl)-trimethyl-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
• 作为产物：
  描述：

  左旋肉碱盐酸盐 、 异丁酰氯 在 三氟乙酸 作用下， 反应 20.0h， 生成 异丁酰基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

• Esters of acyl L-carnitines with gamma-hydroxybutyric acid and pharmaceutical compositions containing them for inhibiting neuronal degeneration and for the treatment of coma
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0442850A1

  公开（公告）日：1991-08-21

  The esters of acyl L-carnitines with gamma-hydroxybutyric acid in the form of pharmacologically acceptable salts of formula (I) wherein X⁻ is the anion of a pharmacologically acceptable salt, e.g. chloride, bromide, orotate, acid aspartate, acid citrate, acid phosphate, acid fumarate, lactate, acid maleate, acid oxalate, acid sulfate and glucosephosphate or in the form of inner salts of formula (I′) wherein R is a straight or branched acyl group having from 2 to 5 carbon atoms, such as e.g. acetyl, propionyl, n-butyryl, isobutyryl and isovaleryl, are active in inhibiting neuronal degeneration (as it occurs in Alzheimer's senile dementia and Parkinson's disease) and in the treatment of coma.

  酰基 L-肉碱与γ-羟基丁酸的酯，其形式为药理学上可接受的式 (I) 盐 其中 X-是药理学上可接受的盐的阴离子，如氯化物、溴化物、乳清酸盐、酸天冬氨酸盐、酸柠檬酸盐、酸磷酸盐、酸富马酸盐、乳酸盐、酸马来酸盐、酸草酸盐、酸硫酸盐和葡萄糖磷酸盐，或以式（I′）内盐的形式存在 其中 R 是具有 2 至 5 个碳原子的直链或支链酰基，如乙酰基、丙酰基、正丁酰基、异丁酰基和异戊酰基等，它们在抑制神经元变性（如阿尔兹海默氏老年痴呆症和帕金森氏病中发生的变性）和治疗昏迷方面具有活性。
• Use of esters of acyl L-carnitines with gamma-hydroxybutyric acid for producing pharmaceutical compositions for the treatment of hepatopathies
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0514357A1

  公开（公告）日：1992-11-19

  Esters of acyl L-carnitine with gamma-hydroxybutyric acid, both as pharmacologically acceptable salts of formula (1) and as inner salts of formula (1') wherein X⁻ is the anion of a pharmacologically acceptable acid and R is a straight or branched acyl group having from 2 to 5 carbon atoms, are used for producing pharmaceutical compositions effective for treating hepatopathies.

  酰基 L-肉碱与γ-羟基丁酸的酯，两者均为药理上可接受的式 (1) 盐 和式 (1') 的内盐 其中 X- 是药理学上可接受的酸的阴离子，R 是具有 2 至 5 个碳原子的直链或支链酰基，用于生产治疗肝病的药物组合物。
• Esters of L-carnitine and acyl L-carnitine endowed with muscle relaxant activityselective on gastrointestinal tract and pharmaceutical compositions containing same
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0559625A2

  公开（公告）日：1993-09-08

  Esters of L-carnitine and acyl L-carnitine of formula (I): wherein R is hydrogen or is a straight or branched, saturated or unsaturated acyl group having 2 to 26 carbon atoms; R1 is a straight or branched, saturated or unsaturated alkyl group having 4 to 26 carbon atoms; and X- is the anion of a pharmacologically acceptable acid are endowed with potent muscle relaxant activity selective on the gastrointestinal tract and are therefore therapeutically useful for treating e.g. adaptive colitis syndromes.

  式 (I) 的 L-肉碱和酰基 L-肉碱的酯： 其中 R 是氢或具有 2 至 26 个碳原子的直链或支链、饱和或不饱和酰基； R1 是具有 4 至 26 个碳原子的直链或支链、饱和或不饱和烷基；以及 X- 是药理学上可接受的酸的阴离子 具有选择性胃肠道肌肉松弛活性，因此可用于治疗适应性结肠炎等综合症。
• 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.
• Zur Darstellung von O-Acyl-Derivaten des Carnitins
  作者：Erich Strack、Irmgard Lorenz

  DOI：10.1515/bchm2.1966.343.1.231

  日期：1966.1