11-deutero-cis,cis,cis-octadeca-9,12,15-trienoic acid ethyl ester | 1526973-96-5

• 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 ethyl ester
• CAS: 1526973-96-5
• 化学式: C₂₀H₃₄O₂
• 分子量: 307.481
• InChiKey: JYYFMIOPGOFNPK-YLXSYYOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  22.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  11-deutero-cis,cis,cis-octadeca-9,12,15-trienoic acid ethyl ester 在 potassium hydroxide 、 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以98%的产率得到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
• 作为产物：
  描述：

  11-deuterooctadeca-9,12,15-triynoic acid ethyl ester 在 sodium tetrahydroborate 、 氢气 、 nickel(II) acetate tetrahydrate 作用下， 以 乙醇 为溶剂， 60.0~70.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以42%的产率得到11-deutero-cis,cis,cis-octadeca-9,12,15-trienoic acid ethyl ester
  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