(9Z,12Z)-[1-13C]-octadeca-9,12-dienoic acid

• 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: (9Z,12Z)-[1-13C]-octadeca-9,12-dienoic acid
• 英文别名: Linoleic Acid-1-13C；(9Z,12Z)-(113C)octadeca-9,12-dienoic acid
• 化学式: C₁₈H₃₂O₂
• 分子量: 281.44
• InChiKey: OYHQOLUKZRVURQ-LKLZSCEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 4-二甲氨基吡啶 、 氢氧化钾 、 草酰氯 、 三氯溴甲烷 、 2-mercaptopyridine-1-oxide sodium salt 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 生成 (9Z,12Z)-[1-13C]-octadeca-9,12-dienoic acid
  参考文献：
  名称：

  Large-scale preparation of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid, (9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid and their [1-13C] all-cis isomers

  摘要：

  Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (> 97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z,12E)-[1-C-13]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z,15E)-[1-C-13]-octadeca-9,12,15-trienoic acid were obtained in, respectively: seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-C-13]-octadeca-9,12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-C-13]-octadeca-9,12,15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities ( > 0.5%) of each labelled fatty acid have been characterised. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(00)00137-7

文献信息

• CAMPBELL, JAMES R.;CLAPP, CHARLES H., BIOORG. CHEM., 17,(1989) N, C. 281-286
  作者：CAMPBELL, JAMES R.、CLAPP, CHARLES H.

  DOI：——

  日期：——