(2R,4'R,8'R)-(5-D3)-α-tocopherol | 113848-10-5

• 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: (2R,4'R,8'R)-(5-D3)-α-tocopherol
• 英文别名: (2R,4'R,8'R)-[C⁵-(2)H3]-α-tocopherol；(C5-_d3)-α-tocopherol；(C5-_d3)-vitamin E；(2R)-2,7,8-trimethyl-5-(trideuteriomethyl)-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
• CAS: 113848-10-5
• 化学式: C₂₉H₅₀O₂
• 分子量: 433.691
• InChiKey: GVJHHUAWPYXKBD-UMLKNSGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  31
• 可旋转键数：
  12
• 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：

  (2R,4'R,8'R)-(5-D3)-α-tocopherol 在 硝酸 、 正丁醇 作用下， 生成 α-tocored
  参考文献：
  名称：

  新型生育酚化合物VIII。形成α-去核反应的反应机理

  摘要：

  建立了一种从α-生育酚（维生素E，1）形成5，6-生育酚二酮（α-tocored，4）的新机理。已显示该反应通过5-烷氧基生育酚中间体进行，其中5a-甲基作为甲醇裂解，这与文献中迄今报道的结果相反。

  DOI：

  10.1016/s0040-4020(97)00076-8
• 作为产物：
  描述：

  天然维生素E 在 氢氧化钾 、 sodium chlorite 、 N-甲基吲哚酮 、 硼氘化钠 、 硫酸 、 氨基磺酸 、 溴 、 重水 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 12.5h， 生成 (2R,4'R,8'R)-(5-D3)-α-tocopherol
  参考文献：
  名称：

  4-Benzyloxy-2-(?,?,?-D3) 甲基苯酚的制备方法、标记的 α-生育酚的结构单元以及 R,R,R-5-D3-?-生育酚的新合成

  摘要：

  描述了合成 4-苄氧基-2-D3-苯酚的不同路线，这是制备 D3-δ-生育酚的关键组成部分。还给出了改善 Minami 还原的条件，允许从广泛可用的 R,R,R 开始以良好的收率合成目标化合物的直接途径和 R,R,R-5-D3-α-生育酚的新合成-α-生育酚。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400535

文献信息

• Tocopherols by Hydride Reduction of Dialkylamino Derivatives
  作者：Thomas Netscher、Francesco Mazzini、Roselyne Jestin

  DOI：10.1002/ejoc.200600874

  日期：2007.3

  and bis(aminomethylated) β-, γ- and δ-tocopherol were then subsequently transformed into the corresponding tocopherols (α- and β-tocopherol) by reductive deamination. As an alternative to classical catalytic hydrogenation in the last step, efficient laboratory protocols using complex hydrides have been derived and applied to the preparation of labelled vitamin E compounds.(© Wiley-VCH Verlag GmbH &

  在改进的条件下，使用衍生自仲胺和多聚甲醛的曼尼希试剂进行氨基甲基化已被用于将非 α-生育酚同系物转化为 α-生育酚，这是生物学上最重要的维生素 E 化合物。随后通过还原脱氨基作用将单和双（氨基甲基化）β-、γ-和δ-生育酚转化为相应的生育酚（α-和β-生育酚）。作为最后一步经典催化氢化的替代方法，使用复合氢化物的高效实验室方案已经推导出并应用于制备标记的维生素 E 化合物。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007 )
• α-Tocopheryl phosphate: Uptake, hydrolysis, and antioxidant action in cultured cells and mouse
  作者：Keiko Nishio、Noriko Ishida、Yoshiro Saito、Yoko Ogawa-Akazawa、Mototada Shichiri、Yasukazu Yoshida、Yoshihisa Hagihara、Noriko Noguchi、John Chirico、Jeffrey Atkinson、Etsuo Niki

  DOI：10.1016/j.freeradbiomed.2011.03.021

  日期：2011.6

  alpha-Tocopheryl phosphate (alpha-TP), a water-soluble analogue of alpha-tocopherol, is found in humans, animals, and plants. alpha-TP is resistant to both acid and alkaline hydrolysis and may exert its own function in this form in vivo. In this study, the uptake, hydrolysis, and antioxidant action of a-TP were measured using alpha-TP with a deuterated methyl group, CD3, at position 5 of the chroman ring (alpha-TP(CD3)). The hydrolysis of alpha-TP(CD3) was followed by measuring alpha-tocopherol containing the CD3 group, alpha-T(CD3), in comparison to unlabeled alpha-tocopherol, alpha-T(CH3). alpha-TP(CD3) was incubated with cultured cells, and the intracellular alpha-T(CD3) formed was measured with HPLC-ECD and GC-MS. alpha-TP(CD3) was also administered to mice for 4 weeks by mixing in the diet, and alpha-T(CD3) was measured in plasma, liver, brain, heart, and testis to compare with endogenous unlabeled alpha-T(CH3). It was found that alpha-TP(CD3) was taken in and hydrolyzed readily to alpha-T(CD3) in cultured cells and in mice. The hydrolysis of alpha-TP(CD3) in cell culture medium was not observed. alpha-TP protected primary cortical neuronal cells from glutamate-induced cytotoxicity, and alpha-TP given to mice reduced the levels of lipid peroxidation products in plasma and liver. These results suggest that alpha-TP is readily hydrolyzed in vivo to alpha-T, which acts as an antioxidant, and that alpha-TP may be used as a water-soluble alpha-T precursor in intravenous fluids, in eye drops, or as a dietary supplement. (C) 2011 Elsevier Inc. All rights reserved.
• Approaches to the Preparation of 4-Benzyloxy-2-(?,?,?-D3)methylphenol, a Building Block for Labeled ?-Tocopherol, and a New Synthesis ofR,R,R-5-D3-?-Tocopherol
  作者：Francesco Mazzini、Alessandro Mandoli、Piero Salvadori、Thomas Netscher、Thomas Rosenau

  DOI：10.1002/ejoc.200400535

  日期：2004.12

  Different routes are described for the synthesis of 4-benzyloxy-2-D3-phenol, a key building block in the preparation of D3-δ-tocopherol. Conditions for the improvement of Minami’s reduction are also given, allowing a straightforward route to the title compound and a new synthesis of R,R,R-5-D3-α-tocopherol in good yields, starting from widely available R,R,R-α-tocopherol. (© Wiley-VCH Verlag GmbH &

  描述了合成 4-苄氧基-2-D3-苯酚的不同路线，这是制备 D3-δ-生育酚的关键组成部分。还给出了改善 Minami 还原的条件，允许从广泛可用的 R,R,R 开始以良好的收率合成目标化合物的直接途径和 R,R,R-5-D3-α-生育酚的新合成-α-生育酚。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Novel tocopherol compounds VIII. Reaction mechanism of the formation of α-tocored
  作者：T. Rosenau、M. Gruner、W.D. Habicher

  DOI：10.1016/s0040-4020(97)00076-8

  日期：1997.3

  A novel mechanism for the formation of 5,6-tocopheryldione (α-tocored, 4) from α-tocopherol (vitamin E, 1) has been established. The reaction has been shown to proceed via a 5-alkoxytocopherol intermediate, with cleavage of the 5a-methyl group as methanol, contrary to results reported so far in the literature.

  建立了一种从α-生育酚（维生素E，1）形成5，6-生育酚二酮（α-tocored，4）的新机理。已显示该反应通过5-烷氧基生育酚中间体进行，其中5a-甲基作为甲醇裂解，这与文献中迄今报道的结果相反。