11-deutero-cis,cis,cis-octadeca-9,12,15-trienoic acid | 1404475-50-8

• 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: 11-deutero-cis,cis,cis-octadeca-9,12,15-trienoic acid
• 英文别名: 11-D-linolenic acid；11-deutero-α-linolenic acid；(9Z,12Z,15Z)-11-deuteriooctadeca-9,12,15-trienoic acid
• CAS: 1404475-50-8
• 化学式: C₁₈H₃₀O₂
• 分子量: 279.427
• InChiKey: DTOSIQBPPRVQHS-LZUMLGDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  1-deuteroocta-2,5-diyn-1-ol 在 吡啶 、 sodium tetrahydroborate 、 copper(l) iodide 、 氢气 、 nickel(II) acetate tetrahydrate 、 三溴化磷 、 potassium carbonate 、 sodium iodide 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， -15.0~70.0 ℃ 、101.33 kPa 条件下， 反应 21.75h， 生成 11-deutero-cis,cis,cis-octadeca-9,12,15-trienoic acid
  参考文献：
  名称：

  Unusual Kinetic Isotope Effects of Deuterium Reinforced Polyunsaturated Fatty Acids in Tocopherol-Mediated Free Radical Chain Oxidations

  摘要：

  Substitution of -CD2- at the reactive centers of linoleic and linolenic acids reduces the rate of abstraction of D by a tocopheryl radical by as much as 36-fold, compared to the abstraction of H from a corresponding -CH2- center. This H. atom transfer reaction is the rate-determining step in the tocopherol-mediated peroxidation of lipids in human low-density lipoproteins, a process that has been linked to coronary artery disease. The unanticipated large kinetic isotope effects reported here for the tocopherol-mediated oxidation of linoleic and linolenic acids and esters suggests that tunneling makes this process favorable.

  DOI：

  10.1021/ja410569g

文献信息

• Unusual Kinetic Isotope Effects of Deuterium Reinforced Polyunsaturated Fatty Acids in Tocopherol-Mediated Free Radical Chain Oxidations
  作者：Connor R. Lamberson、Libin Xu、Hubert Muchalski、J. Rafael Montenegro-Burke、Vadim V. Shmanai、Andrei V. Bekish、John A. McLean、Catherine F. Clarke、Mikhail S. Shchepinov、Ned A. Porter

  DOI：10.1021/ja410569g

  日期：2014.1.22

  Substitution of -CD2- at the reactive centers of linoleic and linolenic acids reduces the rate of abstraction of D by a tocopheryl radical by as much as 36-fold, compared to the abstraction of H from a corresponding -CH2- center. This H. atom transfer reaction is the rate-determining step in the tocopherol-mediated peroxidation of lipids in human low-density lipoproteins, a process that has been linked to coronary artery disease. The unanticipated large kinetic isotope effects reported here for the tocopherol-mediated oxidation of linoleic and linolenic acids and esters suggests that tunneling makes this process favorable.