tridecanoyl carnitine | 142674-35-9

• 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: tridecanoyl carnitine
• 英文别名: 3-tridecanoyloxy-4-(trimethylazaniumyl)butanoate
• CAS: 142674-35-9
• 化学式: C₂₀H₃₉NO₄
• 分子量: 357.534
• InChiKey: OLAOWMDKXPIITQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 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：
  4

反应信息

• 作为产物：
  描述：

  十三酸 在 氯化亚砜 作用下， 以 三氟乙酸 为溶剂， 反应 6.0h， 生成 tridecanoyl 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

• Bis alkanoyl esters of carnitine having bactericidal, fungicidal and antiprotozoal activity
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0796841A1

  公开（公告）日：1997-09-24

  DL-, D- or L-carnitine esters of formula wherein:    R is a straight or branched, saturated or unsaturated alkanoyl group having 2-16 carbon atoms; Y is a straight or branched alkylene chain having 3-6 carbon atoms or ortho, meta or para-xylilene; and    X- is the anion of a pharmacologically acceptable acid which possess potent bactericidal, fungicidal and antiprozoal activity, processes for their preparation and compositions topically applicable for treating infections of the skin, outer ear and mucosa, are disclosed.

  式中的 DL-、D- 或 L-肉碱酯类 其中 R 是具有 2-16 个碳原子的直链或支链、饱和或不饱和烷酰基； Y 是具有 3-6 个碳原子的直链或支链亚烷基，或正位、偏位或对位亚烷基；以及 X- 是药理学上可接受的酸的阴离子，这种酸 本发明公开了具有强效杀菌、杀真菌和抗原虫活性的杀菌剂、杀真菌剂和抗原虫剂的制备方法，以及可局部用于治疗皮肤、外耳和粘膜感染的组合物。
• 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.
• US5925369A
  申请人：——

  公开号：US5925369A

  公开（公告）日：1999-07-20
• 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.