α-tocopheroxyl radical | 95906-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: α-tocopheroxyl radical
• CAS: 95906-80-2
• 化学式: C₂₉H₄₉O₂
• 分子量: 429.707
• InChiKey: DHSYAVGCXXTFLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  10.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-tocopheroxyl radical 在 对叔丁基邻苯二酚 作用下， 以 苯 为溶剂， 生成 α-tocopherol
  参考文献：
  名称：

  A Quantitative Approach to the Recycling of α-Tocopherol by Coantioxidants

  摘要：

  A systematic investigation is reported on the regeneration of alpha-tocopherol (alpha-TOH) in homogeneous solution by coantioxidants in order to better understand the mechanism and the factors responsible for the effectiveness of this process. The current availability of thermochemical data concerning the reactants involved in the regeneration reactions, as well as a large number of the kinetic constants for the various reactions involved, allowed us to rationalize the experimental observations collected so far. Three limiting cases have been considered. The first case is that of a coantioxidant irreversibly regenerating (alpha-TOH, where the effectiveness of the recycling process depends on the magnitude of the rate constant k(r). The second case is that of a coantioxidant reversibly recycling alpha-TOH, where regeneration can only be observed if the bond dissociation enthalpy value of the coantioxidant is lower or at least close to that of the O-H bond of alpha-tocopherol. The third case is that of a catechol derivative (chosen as a model compound for polyphenolic antioxidants), where recycling of alpha-TOH is feasible even though the BDE value is significantly higher than that of vitamin E. In this case, the driving force for the recycling process is the removal of the semiquinone radical from the catechol derivative by the alpha-tocopheroxyl radical, which makes the regeneration of alpha-TOH practically irreversible.

  DOI：

  10.1021/jo026501f
• 作为产物：
  描述：

  天然维生素E 在 Ph₂CHOO radical 作用下， 以 氯苯 为溶剂， 生成 α-tocopheroxyl radical
  参考文献：
  名称：

  Belyakov, Vladimir A.; Roginsky, Vitalij A.; Bors, Wolf, Journal of the Chemical Society. Perkin transactions II, 1995, # 12, p. 2319 - 2326

  摘要：

  DOI：

文献信息

• Belyakov, Vladimir A.; Roginsky, Vitalij A.; Bors, Wolf, Journal of the Chemical Society. Perkin transactions II, 1995, # 12, p. 2319 - 2326
  作者：Belyakov, Vladimir A.、Roginsky, Vitalij A.、Bors, Wolf

  DOI：——

  日期：——
• A Quantitative Approach to the Recycling of α-Tocopherol by Coantioxidants
  作者：Riccardo Amorati、Fiammetta Ferroni、Marco Lucarini、Gian Franco Pedulli、Luca Valgimigli

  DOI：10.1021/jo026501f

  日期：2002.12.1

  A systematic investigation is reported on the regeneration of alpha-tocopherol (alpha-TOH) in homogeneous solution by coantioxidants in order to better understand the mechanism and the factors responsible for the effectiveness of this process. The current availability of thermochemical data concerning the reactants involved in the regeneration reactions, as well as a large number of the kinetic constants for the various reactions involved, allowed us to rationalize the experimental observations collected so far. Three limiting cases have been considered. The first case is that of a coantioxidant irreversibly regenerating (alpha-TOH, where the effectiveness of the recycling process depends on the magnitude of the rate constant k(r). The second case is that of a coantioxidant reversibly recycling alpha-TOH, where regeneration can only be observed if the bond dissociation enthalpy value of the coantioxidant is lower or at least close to that of the O-H bond of alpha-tocopherol. The third case is that of a catechol derivative (chosen as a model compound for polyphenolic antioxidants), where recycling of alpha-TOH is feasible even though the BDE value is significantly higher than that of vitamin E. In this case, the driving force for the recycling process is the removal of the semiquinone radical from the catechol derivative by the alpha-tocopheroxyl radical, which makes the regeneration of alpha-TOH practically irreversible.