α-tocopherol | 86646-82-4

• 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-tocopherol
• 英文别名: 2-Hexadecyl-2,5,7,8-tetramethyl-chroman-6-ol；2-hexadecyl-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol
• CAS: 86646-82-4
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: AHYFKRZPNMNAJL-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C
• 沸点：
  235-245 °C(Press: 0.2 Torr)
• 密度：
  0.932±0.06 g/cm3(Predicted)

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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-tocopherol 在 苯乙烯 、 氧气 作用下， 以 氯苯 为溶剂， 生成 α-tocopheroxyl radical
  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：

  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

文献信息

• Reversible exciplex formation between singlet oxygen, 1.DELTA.g, and vitamin E. Solvent and temperature effects
  作者：Anthony A. Gorman、I. R. Gould、I. Hamblett、M. C. Standen

  DOI：10.1021/ja00335a014

  日期：1984.11

  Determination de la vitesse et des parametres activations des reactions de l'oxygene singulet avec l'α-tocopherol, le pentamethyl-2,2,5,7,8 chromannol-6 et le tri-t-butyl-2,4,6 phenol dans cinq solvents

  Determination de la vitesse et des parametres activations des reactors de l'oxygene singulet avec l'α-tocopherol, le pentamethyl-2,2,5,7,8 chromannol-6 et le tri-t-butyl-2,4,6苯酚 dans cinq 溶剂
• INHIBITORS OF HEMEPROTEIN-CATALYZED LIPID PEROXIDATION
  申请人：VANDERBILT UNIVERSITY

  公开号：US20150368241A1

  公开（公告）日：2015-12-24

  Compounds, compositions and methods related to the prevention or treatment of isoprostane-mediated tissue damage in a mammalian subject in need thereof.

  与哺乳动物受体内异前列腺素介导的组织损伤的预防或治疗相关的化合物、组合物和方法。
• Nitrosation-oxidative ring contraction of α-tocopherol by reaction with nitric oxide under aerobic conditions
  作者：Marco d'Ischia

  DOI：10.1016/0040-4039(95)01846-a

  日期：1995.11

  Exposure of α-tocopherol (1) to nitric oxide (NO) in air-saturatcd cyclohexane leads to a complex mixture of products, one of which, relatively more polar, has been isolated and identified as the novel 2,3-dimethyl-4-acetyl-4-hydroxy-5-nitroso-2-cyclopentenone derivative 5.

  在空气饱和的环己烷中将α-生育酚（1）暴露于一氧化氮（NO）会导致生成复杂的产物混合物，其中一种极性相对较大的产物已被分离出来，并被鉴定为新颖的2,3-二甲基-4 -乙酰基-4-羟基-5-亚硝基-2-环戊烯酮衍生物5。
• NOVEL CHAIN-BREAKING ANTIOXIDANTS
  申请人：Pratt Derek A.

  公开号：US20100041683A1

  公开（公告）日：2010-02-18

  Compounds, preferably 5-pyrimidinol and 3-pyridinol derivatives, that act as effective chain breaking antioxidants of both the lipid and water-soluble variety (analogous to the natural Vitamins E and C), many of which are more reactive toward peroxyl radicals than the most potent form of Vitamin E. These compounds may exhibit many chemopreventive effects associated with conditions in which free radical-mediated cellular damage or disruption is implicated and Vitamins E and C are shown to have protective effects. Additionally, these compounds should be excellent oxidation inhibitors as additives to fuels, lubricants, rubber, polymers, chemicals, solvents and foodstuffs.

  这段话的意思是：化合物，最好是5-嘧啶醇和3-吡啶醇衍生物，可作为有效的链断裂抗氧化剂，既能作用于脂质又能作用于水溶性类似于天然维生素E和C，其中许多化合物对过氧自由基的反应性比维生素E最强的形式还要高。这些化合物可能表现出许多与自由基介导的细胞损伤或破坏有关的化学预防效应，并且已经证明维生素E和C具有保护作用。此外，这些化合物应该是优秀的氧化抑制剂，可作为添加剂添加到燃料、润滑剂、橡胶、聚合物、化学品、溶剂和食品中。
• Mitochondria-Targeted Antioxidant Prodrugs and Methods of Use
  申请人：Anders Marion W.

  公开号：US20090306125A1

  公开（公告）日：2009-12-10

  The present invention is a mitochondria-targeted antioxidant prodrug useful for the prevention or treatment of diseases or conditions associated with mitochondrial dysfunction resulting from changes in the mitochondrial redox environment. Antioxidant prodrugs of the invention are produced by modifying an antioxidant to a fatty acid so that the resulting prodrug is targeted to and activated by an enzyme of mitochondrial fatty acid beta-oxidation.

  本发明是一种线粒体定位的抗氧化剂前药，可用于预防或治疗与线粒体氧化还原环境变化导致的线粒体功能障碍相关的疾病或病症。本发明的抗氧化剂前药通过将抗氧化剂修饰为脂肪酸，使得得到的前药能够定位并被线粒体脂肪酸β-氧化酶激活。