nonanoyl carnitine

• 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: nonanoyl carnitine
• 英文别名: O-nonanoyl-L-carnitine；(3R)-3-nonanoyloxy-4-(trimethylazaniumyl)butanoate
• 化学式: C₁₆H₃₁NO₄
• 分子量: 301.426
• InChiKey: MPSPNFAQQQMFLK-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  nonanoyl carnitine 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 nonanoyl-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：

  壬酸 在 氯化亚砜 、 三氯乙酸 作用下， 反应 22.0h， 生成 nonanoyl carnitine
  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

• An LC-MS/MS method to quantify acylcarnitine species including isomeric and odd-numbered forms in plasma and tissues
  作者：Pieter Giesbertz、Josef Ecker、Alexander Haag、Britta Spanier、Hannelore Daniel

  DOI：10.1194/jlr.d061721

  日期：2015.10

  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.
• Characterization of acylcarnitines using fast atom bombardment mass spectrometry and gas chromatography/mass spectrometry
  作者：J. F. Van Bocxlaer、M. Claeys、H. Van Den Heuvel、A. P. De Leenheer

  DOI：10.1002/jms.1190300112

  日期：1995.1

  Mass spectral data are reported for an extended series of synthesized acylcarnitines. Direct mass spectrometry was performed using ionization by fast atom bombardment in combination with high-energy collisional activation and B/E linked scanning. The data show that it is possible to distinguish between isomeric compounds using this technique. Gas chromatographic/mass spectrometric analysis data for acylcarnitines, as their acyloxylactone derivatives, are reported. Both electron impact and chemical ionization modes were used, permitting the unequivocal characterization and identification of the various compounds. In view of the recent marked increase in acylcarnitine profiling activities, the comprehensively reported mass spectrometric and gas chromatographic data may be useful for reference purposes.

  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。