异丁酰基-L-肉碱 | 25518-49-4

• 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
• 中文别名: 异丁酰-L-肉碱
• 英文名称: isobutyryl-L-carnitine
• 英文别名: isobutyrylcarnitine；(3R)-3-(2-methylpropanoyloxy)-4-(trimethylazaniumyl)butanoate
• CAS: 25518-49-4
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: LRCNOZRCYBNMEP-SECBINFHSA-N

物化性质

• 溶解度：
  DMSO：250mg/mL（1080.89mM）；水：125 mg/mL（540.45 mM）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 储存条件：
  | 2-8°C |

制备方法与用途

生物活性的 Isobutyryl-L-carnitine 是酰基辅酶 A 脱氢酶的产物。靶点为人内源性代谢物。

反应信息

• 作为反应物：
  描述：

  异丁酰基-L-肉碱 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 isobutyryl-L-carnitine oxylactone
  参考文献：
  名称：

  Characterization of acylcarnitines using fast atom bombardment mass spectrometry and gas chromatography/mass spectrometry

  摘要：

  报告了一系列合成酰基肉碱的质谱数据。采用快速原子轰击离子化技术结合高能碰撞激发和B/E连扫的直接质谱方法。数据显示，可以使用该技术区分异构化合物。报告了以酰氧乳酸酯衍生物形式的酰基肉碱的气相色谱/质谱分析数据。使用了电子轰击和化学电离两种模式，这使得各种化合物的特征和鉴定变得明确无误。鉴于最近酰基肉碱分析活动的显著增加，详细报告的质谱和气相色谱数据可能对参考目的有所帮助。

  DOI：

  10.1002/jms.1190300112
• 作为产物：
  描述：

  左旋肉碱盐酸盐 、 异丁酰氯 在 三氯乙酸 作用下， 反应 18.0h， 生成 异丁酰基-L-肉碱
  参考文献：
  名称：

  An LC-MS/MS method to quantify acylcarnitine species including isomeric and odd-numbered forms in plasma and tissues

  摘要：

  Acylcarnitines are intermediates of fatty acid and amino acid oxidation found in tissues and body fluids. They are important diagnostic markers for inherited diseases of peroxisomal and mitochondrial oxidation processes and were recently described as biomarkers of complex diseases like the metabolic syndrome. Quantification of acylcarnitine species can become challenging because various species occur as isomers and/or have very low concentrations. Here we describe a new LC-MS/MS method for quantification of 56 acylcarnitine species with acyl-chain lengths from C2 to C18. Our method includes amino acid-derived positional isomers, like methacrylyl-carnitine (2-M-C3:1-CN) and crotonyl-carnitine (C4:1-CN), and odd-numbered carbon species, like pentadecanoyl-carnitine (C15:0-CN) and heptadecanoyl-carnitine (C17:0-CN), occurring at very low concentrations in plasma and tissues. Method validation in plasma and liver samples showed high sensitivity and excellent accuracy and precision. In an application to samples from streptozotocin-treated diabetic mice, we identified significantly increased concentrations of acylcarnitines derived from branched-chain amino acid degradation and of odd-numbered straight-chain species, recently proposed as potential biomarkers for the metabolic syndrome. In conclusion, the LC-MS/MS method presented here allows robust quantification of isomeric acylcarnitine species and extends the palette of acylcarnitines with diagnostic potential derived from fatty acid and amino acid metabolism.

  DOI：

  10.1194/jlr.d061721

文献信息

• [EN] L-CARNITINE AND ALKANOYL L-CARNITINE PHYTATES AND PROCESS FOR PREPARING THE SAME<br/>[FR] PHYTATES DE L-CARNITINE ET D'ALCANOYLE L-CARNITINE, ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：SCIAN LAB LLC

  公开号：WO2010005465A1

  公开（公告）日：2010-01-14

  Salts of L-carnitine and alkanoyl L-carnitines with phytic acid of general formula (I), and the process of preparing the same, wherein the mole ratio between the L-carnitine or its alkanoyl derivatives cation and phytic acid anion be within the range of 1 :1 to 6:1, wherein: n = 1-6; R1 is the phytate anion; R is either hydrogen, a straight alkanoyl group having 2-12 carbon atoms or a branched-chain alkanoyl group having 2-12 carbon atoms.

  L-肉碱盐和烷酰基L-肉碱盐与一般公式(I)的植酸，以及制备这些化合物的过程，其中L-肉碱或其烷酰衍生物阳离子与植酸阴离子之间的摩尔比在1:1至6:1的范围内，其中：n = 1-6；R1为植酸阴离子；R为氢、具有2-12个碳原子的直链烷酰基团或具有2-12个碳原子的支链烷酰基团。
• L-carnitine and alkanoyl L-carnitine phytates and process for preparing the same
  申请人：Chen Jian

  公开号：US20100317890A1

  公开（公告）日：2010-12-16

  Salts of L-carnitine and alkanoyl L-carnitines with phytic acid of general formula (I), and the process of preparing the same, wherein the mole ratio between the L-carnitine or its alkanoyl derivatives cation and phytic acid anion be within the range of 1:1 to 6:1, wherein: n=1-6; R 1 is the phytate anion; R is either hydrogen, a straight alkanoyl group having 2-12 carbon atoms or a branched-chain alkanoyl group having 2-12 carbon atoms.

  L-肉碱盐和辛酰基L-肉碱盐与通式(I)的植酸，以及其制备方法，其中L-肉碱或其辛酰基衍生物阳离子与植酸阴离子之间的摩尔比在1:1至6:1的范围内，其中：n=1-6；R1是植酸阴离子；R是氢，具有2-12个碳原子的直链辛酰基或具有2-12个碳原子的支链辛酰基。
• Use of L-carnitine derivatives for the manufacture of a medicament for the therapeutical treatment of peripheral neuropathies
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0376899A2

  公开（公告）日：1990-07-04

  The use is disclosed of compounds of general formula wherein: Y is hydrogen, methyl or amino, and R is an unsubstituted or substituted alkyl group selected from methyl, ethyl, 1-methylpropyl, isobutyl, isopropyl, mercaptomethyl and 3-guanidinopropyl and the pharmacologically acceptable salts thereof, for treating degenerative alterations of the nervous system. The compounds can be administered orally or parenterally.

  公开了通式如下的化合物的用途 其中 Y 是氢、甲基或氨基，以及 R 是选自甲基、乙基、1-甲基丙基、异丁基、异丙基、巯基甲基和 3-胍基丙基的未取代或取代的烷基。 及其药理上可接受的盐类，用于治疗神经系统的退行性改变。这些化合物可以口服或肠外给药。
• 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。
• Esters of (R)(-)-carnitine and acyl (R)(-)-carnitines with beta-hydroxybutyric acid and pharmaceutical compositions containing them for inhibiting neuronal degeneration, liver proteolysis and for the treatment of coma
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0443996A1

  公开（公告）日：1991-08-28

  The esters of (R)(-)-carnitine and acyl (R)(-)-carnitines with beta-hydroxybutiric 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 hydrogen or 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), liver proteolysis and in the treatment of coma.

  (R)(-)-卡尼汀和酰基(R)(-)-卡尼汀与β-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，例如氯化物、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 为氢或具有 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，它们在抑制神经元变性（如发生在阿尔茨海默氏症老年痴呆症和帕金森氏症中）、肝脏蛋白分解和治疗昏迷方面具有活性。