α-tocopherylquinone | 27696-11-3

• 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: α-tocopherylquinone
• 英文别名: α-tocopherylchinon；α-tocopherolquinone；Tocopherolchinon；alpha-Tocopherylquinone；2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
• CAS: 27696-11-3
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: LTVDFSLWFKLJDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  535.8±29.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-tocopherylquinone 、 氯化锌 生成 Trimethylphytylbenzoquinone
  参考文献：
  名称：

  ZAXAROVA, E. I.;SHUANNOV, K. A.-V.;ALEKSEEV, S. M.;EVSTIGNEEVA, R. N., KISLORODSODERZHASHCHIE GETEROTSIKLY: BCEC. SOVESHCH.: TEZ. DOKL./KRASNODA+

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Methyl-2-[2,5,7,8-tetramethyl-6-oxo-2-(4,8,12-trimethyl-tridecyl)-2,3,4,6-tetrahydro-chromen-8a-ylperoxy]-propionitrile 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 α-tocopherylquinone
  参考文献：
  名称：

  Products of stoichiometry of reaction of vitamin E with alkylperoxy radicals

  摘要：

  DOI：

  10.1021/jo00177a021

文献信息

• Bromination of Tocopherols: Oxidative Halogenations and Rearrangements
  作者：Stefan Böhmdorfer、Anjan Patel、Andreas Hofinger、Thomas Netscher、Lars Gille、Thomas Rosenau

  DOI：10.1002/ejoc.201100153

  日期：2011.6

  pathways (oxidation, substitution, condensation, elimination) than the acidic conditions did. The para-quinones were major reaction products observed for all four tocopherols. Interestingly, if the quinone was substituted at C-5, it rearranged in a Michael-type addition process followed by substitution with a bromonium ion. The absence of a substituent at C-5, the presence of a bromine atom at C-7, or the

  研究了所有四种生育酚和相应模型化合物在酸性和碱性水性介质中的溴化行为。酸性条件产生醌和溴化醌，生育酚的溴化在氧化成醌之前。缓冲液类型和浓度不影响反应结果，而 pH 值和缓冲液与用作共溶剂的乙醇的比例强烈影响反应速率。在碱性介质中，获得了两种或三种主要产物和大量次要副产物，因为氧化次溴酸盐和碱性条件的组合允许比酸性条件更复杂的反应途径（氧化、取代、缩合、消除）。对醌是所有四种生育酚的主要反应产物。有趣的是，如果醌在 C-5 处被取代，它会在迈克尔型加成过程中重新排列，然后用溴离子取代。C-5 处没有取代基、C-7 处存在溴原子或反应介质中不存在溴都能够阻止该反应。通过用新获得的溴基团取代羟基，重排产物可以进一步反应。在γ-和δ-生育酚的情况下，进一步的重排导致三氧化合物的形成。通过用新获得的溴基团取代羟基，重排产物可以进一步反应。在 γ- 和 δ-生育酚的情况下，进一步的重排导致形成三氧化合
• Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
  申请人：Miller M. Guy

  公开号：US20060281809A1

  公开（公告）日：2006-12-14

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  披露了治疗或抑制线粒体疾病的方法，如弗里德赖希共济失调（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、卒中（MELAS）或科恩斯-赛尔综合征（KSS），以及在本发明方法中有用的化合物，如α-生育酚醌。还披露了用于治疗其他疾病的方法和化合物。还披露了用于评估受试者代谢状态和治疗效果的能量生物标志物。还披露了调节、正常化或增强能量生物标志物的方法，以及用于这些方法的化合物。
• [EN] QUINONES AND PROCESS OF OBTAINING SAME<br/>[FR] QUINONES ET PROCÉDÉ D'OBTENTION ASSOCIÉ
  申请人：BASF SE

  公开号：WO2019158514A1

  公开（公告）日：2019-08-22

  Disclosed is a process for the oxidation of at least one chroman (C1) in a solvent mixture comprising at least two solvents or in a C-bearing solvent, with a gaseous compound comprising, essentially consisting of, or consisting of oxygen in the presence of a copper catalyst, said copper catalyst exhibiting the oxidation state (+1) or (+2). A further part of the disclosure is a composition comprising at least one chroman (C1) and/or at least one quinone (C30), a solvent mixture comprising at least two solvents or a C-bearing solvent, a copper catalyst, said copper catalyst exhibiting the oxidation state (+1) or (+2) and a gaseous compound comprising, essentially consisting or consisting of oxygen. A quinone preparation and a process of making same is also part of the invention.

  本文揭示了一种在至少两种溶剂组成的溶剂混合物中，或者在含碳溶剂中，利用氧气气态化合物在铜催化剂存在下氧化至少一种色基酚（C1）的过程，所述铜催化剂呈现氧化态（+1）或（+2）。本文的另一部分揭示了一种组合物，包括至少一种色基酚（C1）和/或至少一种醌（C30），至少两种溶剂组成的溶剂混合物或含碳溶剂，铜催化剂，所述铜催化剂呈现氧化态（+1）或（+2），以及包含氧气的气态化合物。醌制备方法及其制备过程也是本发明的一部分。
• Novel tocopherol compounds I. Bromination of α-tocopherol — reaction mechanism and synthetic applications
  作者：T. Rosenau、W.D. Habicher

  DOI：10.1016/0040-4020(95)00421-4

  日期：1995.7

  including the occurrence of an ortho-quinone methide, not as a radical-chain reaction, contrary to earlier reports. The ortho-quinone methide intermediate is also produced by oxidation of a-tocopherol with silver oxide and can be trapped in the presence of electron-rich dienophiles in a hetero-Diels-Alder reaction to form novel dichromanes in high yields.

  与较早的报道相反，α-生育酚的溴化过程显示为两步过程，其中包括邻醌甲基化物的发生，而不是自由基链反应。邻苯二甲酮甲基化物中间体也可通过α-生育酚与氧化银的氧化反应制得，并可在富电子二烯亲和体存在下，通过杂Diels-Alder反应捕获，以高收率形成新型重铬烷。
• Side-chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
  申请人：Miller M. Guy

  公开号：US20070225261A1

  公开（公告）日：2007-09-27

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  本发明揭示了治疗或抑制线粒体疾病的方法，例如弗里德雷希共济失调症（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、中风（MELAS）或克恩斯-萨耶综合征（KSS），以及在该方法中有用的化合物。还揭示了用于治疗其他疾病的方法和化合物。还揭示了有用于评估受试者代谢状态和治疗效果的能量生物标志物。还揭示了调节、规范或增强能量生物标志物的方法，以及用于此类方法的化合物。