tocol radical | 34004-57-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tocol radical
• CAS: 34004-57-4
• 化学式: C₂₆H₄₃O₂
• 分子量: 387.626
• InChiKey: KCNLTSMYRHJCPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.35
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.13
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-甲基-2-(4,8,12-三甲基十三烷基)-6-色满醇 在 加尔万氧基自由基 作用下， 以 乙醇 为溶剂， 生成 tocol radical
  参考文献：
  名称：

  新型抗氧化剂自由基吸收能力测定方法的开发：烷基自由基吸收能力（ARAC）

  摘要：

  提出了一种新的自由基吸收能力测定方法，该方法利用了烷基基团（2,6-二叔丁基-4-（4'-甲氧基苯基）苯氧基基团）和停止流动光谱法，被称为烷基基团吸收法容量（ARAC）分析方法。通过测量乙醇中的自由基清除速率常数，确定每种生育酚的自由基吸收能力（ARAC值）。还可以通过在清除反应过程中测量烷基的半衰期来评估ARAC值。对于自由基吸收能力的估计，与DPPH自由基，加尔维诺尔和p相比，烷基更适合-硝基苯基硝酰基硝基氧。生育酚中的ARAC值显示出与先前报道的自由基吸收能力相同的趋势，并且该趋势与参与清除反应的氧自由基以及围绕生育酚和氧自由基的介质无关。ARAC值可以直接与清除自由基的速率常数相关，并且ARAC方法的优点是可以在用户友好的有机溶剂（乙醇）中处理稳定且可分离的自由基（芳氧基）。ARAC方法也已成功应用于棕榈油提取物。因此，ARAC方法可用于抗氧化剂和食品的自由基吸收能力测定。

  DOI：

  10.1021/jf402811m

文献信息

• Synthesis and kinetic study of antioxidant activity of new tocopherol (vitamin E) compounds
  作者：Kazuo Mukai、Yukio Kageyama、Tamie Ishida、Kazuyuki Fukuda

  DOI：10.1021/jo00264a010

  日期：1989.2
• Mechanism of antioxidant reaction of vitamin E: charge transfer and tunneling effect in proton-transfer reaction
  作者：Shinichi Nagaoka、Aya Kuranaka、Hideki Tsuboi、Umpei Nagashima、Kazuo Mukai

  DOI：10.1021/j100185a065

  日期：1992.3

  In order to shed light on the mechanism of proton-transfer reactions, a kinetic and ab initio study of the antioxidant action (intermolecular proton transfer) of vitamin E derivatives has been carried out. The second-order rate constants (k(s)'s) for the reaction of tocopherols (TocH's) with variously substituted phenoxyl radicals (PhO.'s) in ethanol were measured with a stopped-flow spectrophotometer. The half-wave reduction potentials (E1/2's) of PhO.'s were obtained by using a cyclic voltammetry technique. The result indicates that k(s) increases as the total electron-donating capacity of the alkyl substituents at the aromatic ring of TocH or the electron-withdrawing capacity of the substituent of PhO. increases. k(s) for the reaction of deuterated tocopherol derivatives (TocD's) with a PhO. in deuterated ethanol (C2H5OD, ethanol-d1) was also measured. A substantial deuterium kinetic isotope effect on k(s) is observed. In the reactions of each PhO. with various TocH's, a plot of log k(s) vs peak oxidation potential (E(p)) of TocH is found to be linear. The slope of its plot for TocD's is clsoe to that for TocH's. In the reactions of each TocH with various PhO.'s, a plot of log k(s) vs E1/2 of PhO. is found to be linear. The geometries of TocH's were optimized with the semiempirical modified neglect of diatomic overlap (MNDO) method. The Koopmans' theorem first ionization energies (IP) for those geometries were calculated with the ab initio method. In the reactions of a PhO. with various TocH's, plots of log k(s) vs IP, the activation energy (E(act)) vs IP, and E(p) vs IP are also found to be linear. From these results, it is considered that both the charge transfer and the proton tunneling play important roles in the antioxidant reaction of TocH. The transition state has the property of the charge-transfer species. The proton tunneling takes place below the transition state. Tunneling allows the proton to cut a corner on the potential energy surface. Our explanation will be widely applicable to many proton-transfer reactions.
• A kinetic study of reactions of tocopherols with a substituted phenoxyl radical
  作者：Kazuo Mukai、Kazuyuki Fukuda、Kunihiko Tajima、Kazuhiko Ishizu

  DOI：10.1021/jo00237a040

  日期：1988.1