6-O-acetyl-5-formyl-(2R,4'R,8'R)-γ-tocopherol | 835613-32-6

• 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: 6-O-acetyl-5-formyl-(2R,4'R,8'R)-γ-tocopherol
• 英文别名: [(2R)-5-formyl-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] acetate
• CAS: 835613-32-6
• 化学式: C₃₁H₅₀O₄
• 分子量: 486.736
• InChiKey: SHAZHWHOHJAXRB-CEFNRUSXSA-N

物化性质

• 沸点：
  571.7±50.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-5-formyl-(2R,4'R,8'R)-γ-tocopherol 在 氢氧化钾 、 sodium chlorite 、 氨基磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 2.5h， 生成 (2R,4'R,8'R)-γ-tocopherol-5-carboxylic acid
  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
• 作为产物：
  描述：

  天然维生素E 在 N-甲基吲哚酮 、 硫酸 、 溴 、 溶剂黄146 作用下， 以 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 6-O-acetyl-5-formyl-(2R,4'R,8'R)-γ-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

• [EN] NITROALKENE TOCOPHEROLS AND ANALOGS THEREOF FOR USE IN THE TREATMENT AND PREVENTION OF INFLAMMATION RELATED CONDITIONS<br/>[FR] NITROALCÈNE-TOCOPHÉROLS ET ANALOGUES DE CEUX-CI UTILISABLES DANS LE CADRE DU TRAITEMENT ET DE LA PRÉVENTION D'AFFECTIONS ASSOCIÉES À L'INFLAMMATION
  申请人：COMPLEXA INC

  公开号：WO2015073527A1

  公开（公告）日：2015-05-21

  Within the scope of the present invention is a new pharmacological strategy for the treatment of atherosclerosis based on the main pathogenic role that low density lipoproteins and chronic inflammation play in atherogenesis. This pharmacological approach implies that the hybrid compound would be selectively incorporated into the lipoproteins particles during the normal metabolism and due to the presence of the chromanol structure of tocopherol. Once the nitroalkene-vitamin E-analog is incorporated into the LDL, this lipoprotein will carry it all over the body, including the atherosclerotic lesions, where the hybrid compound will be able to exert the potent anti-inflammatory and anti-atherogenic properties similar to nitrated fatty acids but without the disadvantages of β-oxidation and lack of control over the targeting and localization of the compound.

  本发明涉及一种基于低密度脂蛋白和慢性炎症在动脉粥样硬化病变中发挥主要致病作用的新药物治疗策略。这种药物治疗方法意味着，杂交化合物将在正常代谢过程中通过生物反应合成被选择性地纳入到脂蛋白粒子中，并由于生育酚的色酰基结构的存在。一旦硝基烯醇-维生素E类似物被纳入到低密度脂蛋白中，这种脂蛋白将携带它遍布全身，包括动脉粥样硬化病变的部位，其中杂交化合物将能够发挥类似于硝酸脂肪酸的强效抗炎和抗动脉粥样硬化作用，但不会出现β-氧化和化合物的靶向和定位的缺点。
• REDOX-ACTIVE THERAPEUTICS FOR TREATMENT OF MITOCHONDRIAL DISEASES AND OTHER CONDITIONS AND MODULATION OF ENERGY BIOMARKERS
  申请人：Miller Guy M.

  公开号：US20100222436A1

  公开（公告）日：2010-09-02

  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.

  本发明揭示了治疗或抑制线粒体疾病的方法，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）或柯恩斯-萨耶综合症（KSS），以及在所述方法中有用的化合物，如α-生育酚醌。本发明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。本发明还揭示了调节、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。
• Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
  申请人：Miller Guy M.

  公开号：US11021424B2

  公开（公告）日：2021-06-01

  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.

  本发明公开了治疗或抑制线粒体疾病的方法，如弗里德雷希共济失调（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、中风（MELAS）或卡恩斯-赛尔综合征（KSS），以及用于本发明方法的化合物，如α-生育酚醌。本发明还公开了用于治疗其他疾病的方法和化合物。本发明还公开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。还公开了调节、正常化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。
• Synthesis and antioxidant properties of novel α-tocopherol glycoconjugates
  作者：Anil K. Singh、K. Gopu

  DOI：10.1016/j.tetlet.2009.12.078

  日期：2010.2

  Glycoconjugates of alpha-tocopherol (1), synthesized using click chemistry between alpha-tocopherol-azide and glyco-alkynes are solids, have enhanced water solubility and exhibit radical-scavenging activities comparable to 1, as determined by DPPH and lipid peroxidation assay methods. (C) 2009 Elsevier Ltd. All rights reserved.
• Easy route to labeled and unlabeled R,R,R-γ-tocopherol by aryl demethylation of α-homologues
  作者：Francesco Mazzini、Thomas Netscher、Piero Salvadori

  DOI：10.1016/j.tet.2004.11.047

  日期：2005.1

  The interest in vitamin E research is increasingly focusing on the peculiar properties of the less investigated tocopherols and their metabolites, such as gamma-tocopherol, which have been revealed as very important for human health. Metabolic studies of gamma-tocopherol have been constricted by its high cost and the poor availability of stable isotope-labeled forms. An efficient, inexpensive and simple route is described for the preparation of labeled and unlabeled R,R,R-gamma-tocopherol, starting from R,R,R-a-tocopherol, through simple thermal decarboxylation of gamma-tocopherol-5-carboxylic acid. (C) 2004 Elsevier Ltd. All rights reserved.