2-methoxy-octadecanal | 34808-62-3

• 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: 2-methoxy-octadecanal
• CAS: 34808-62-3
• 化学式: C₁₉H₃₈O₂
• 分子量: 298.51
• InChiKey: KABBEVOXIJSQAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  21.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  甲醇 、 2-chloro-octadecanal 在 盐酸 作用下， 反应 1.5h， 生成 2-methoxy-octadecanal
  参考文献：
  名称：

  Strategies for the analysis of chlorinated lipids in biological systems

  摘要：

  Myeloperoxidase-derived HOCl reacts with the vinyl ether bond of plasmalogens yielding alpha-chlorofatty aldehydes. These chlorinated aldehydes can be purified using thin-layer chromatography, which is essential for subsequent analysis of extracts from some tissues such as myocardium. The alpha-chlorofatty aldehyde 2-chlorohexadecanal (2-ClHDA) is quantified after conversion to its pentafluorobenzyl oxime derivative using gas chromatography-mass spectrometry and negative-ion chemical ionization detection. 2-ClHDA accumulates in activated human neutrophils and monocytes, as well as in atherosclerotic lesions and infarcted myocardium. Metabolites of 2-ClHDA have also been identified, including the oxidation product, 2-chlorohexadecanoic acid (2-ClHA), and the reduction product, 2-chlorohexadecanol. 2-ClHA can be quantified using LC-MS with selected reaction monitoring (SRM) detection. 2-ClHA can be omega-oxidized by hepatocytes and subsequently beta-oxidized from the omega-end, leading to the production of the dicarboxylic acid, 2-chloroadipic acid. This dicarboxylic acid is excreted in the urine and can also be quantified using LC-MS methods with SRM detection. Quantitative analyses of these novel chlorinated lipids are essential to identify the role of these lipids in leukocyte-mediated injury and disease. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2012.06.013