2-Hydroxy-2-methyl-4-(2,5,6-trimethyl-2,4-dioxo-2,5-cyclohexadienyl)butanoic acid | 57028-37-2

• 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: 2-Hydroxy-2-methyl-4-(2,5,6-trimethyl-2,4-dioxo-2,5-cyclohexadienyl)butanoic acid
• 英文别名: 2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanoic acid；TroloxQ；2-Hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid
• CAS: 57028-37-2
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: OIKYKCSVMZWTOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  454.5±45.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-2-methyl-4-(2,5,6-trimethyl-2,4-dioxo-2,5-cyclohexadienyl)butanoic acid 在 氧气 作用下， 生成 2,3,5-trimethyl-6-(3-oxobutyl)-1,4-benzoquinone
  参考文献：
  名称：

  Photo-induced damage mitigating agents and preparation and methods of use thereof

  摘要：

  本发明涉及用于减少和/或预防光照分析反应中一个或多个反应物的光诱导损伤的组合物、装置、系统和方法，通过向反应混合物中添加一个或多个光诱导损伤缓解剂，并允许反应进行一段时间，该时间小于光诱导损伤阈值时间。

  公开号：

  US08388982B2
• 作为产物：
  描述：

  奎诺二甲基丙烯酸酯 在 溴 、 potassium bromide 作用下， 以14%的产率得到2-Hydroxy-2-methyl-4-(2,5,6-trimethyl-2,4-dioxo-2,5-cyclohexadienyl)butanoic acid
  参考文献：
  名称：

  trolox c（一种生育酚类似物）在水溶液中的氧化和反应。脉冲辐射研究

  摘要：

  Trolox c, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carb acid, 1，一种水溶性的 {α}-tocopherol 类似物，被氧化Br{sub 2}{sup {minus}} 得到苯氧基自由基 2。这些自由基通过二阶、pH 依赖性过程歧化得到 1 和不稳定的中间体 3，鉴定为 4,5-二氢-3， 6,8,9-四甲基-2H-3,9a-epoxy-1-benzoxepin-2,7(3H)-dione，在 235 nm 处有很强的紫外吸收。歧化速率常数随着 pH 值的增加而降低，最大的变化发生在 pH 值 2 和 9 之间，在那里它降低了 10{sup 4}。速率常数与 pH 值关系图与涉及质子化和非质子化形式 2 的三个反应的方案一致。中间体 3 经历缓慢的 pH 依赖性分解为 2-羟基-2-甲基-4-(2

  DOI：

  10.1021/ja00191a031

文献信息

• Process for the manufacture of 3,4-dihydro-benzopyran derivatives and starting materials in this process
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0003221A2

  公开（公告）日：1979-08-08

  The invention is concerned with a novel process for the manufacture of chromane derivatives of the formula wherein R, R1, R2 and R3 are hydrogen or lower alkyl and R4 is lower alkyl. This process comprises reducing a compound of the formula wherein R', R2 and R3 are hydrogen or lower alkyl and R', R4 and R5 are lower alkyl, in a polar solvent in the presence of a base. The invention is further concerned with the novel compounds of formula II which are used as starting materials. The compounds of formula are, inter alia, valuable intermediates in the synthesis of vitamin E.

  本发明涉及一种制造式中 R、R1、R2 和 R3 为氢或低级烷基，R4 为低级烷基的铬烷衍生物的新工艺。 该工艺包括在极性溶剂中，在碱存在下还原式中 R'、R2 和 R3 为氢或低级烷基，R'、R4 和 R5 为低级烷基的化合物。 本发明还涉及用作起始原料的新型式 II 化合物。 除其他外，式化合物是合成维生素 E 的重要中间体。
• Hydroquinone derivative and pharmaceutical use thereof
  申请人：JAPAN ENERGY CORPORATION

  公开号：EP0831092A2

  公开（公告）日：1998-03-25

  Disclosed is a hydroquinone derivative or a pharmaceutically acceptable salt thereof, the hydroquinone derivative being represented by formula (I): wherein R1 is a phenyl group which is unsubstituted or substituted with a substituent or substituents each independently selected from the group consisting of a halogen atom, a C1-4 alkyl group and a C1-4 alkoxy group; R2 is a hydrogen atom or a C1-4 alkyl group; each of R3 and R4 is independently a hydrogen atom or a C1-4 alkyl group; R5 is a hydrogen atom or a C1-4 alkyl group; each of R6, R7 and R8 is independently a hydrogen atom or a C1-4 alkyl group; P is a hydroxyl group; Q is a hydroxyl group, a C1-4 alkoxy group, a C1-18 acyloxy group or an oxo group; P may form together with Q an ether bond; R is a hydroxyl group, a C1-4 alkoxy group, a C1-18 acyloxy group or an oxo group, provided that when one of said Q and said R is an oxo group, the other is also an oxo group; X is a single bond, an -NR10- group or a -CH2-NR10- group in which R10 is a hydrogen atom or a C1-4 alkyl group; Y is a methylene group or a carbonyl group; and    dotted bonds in a six membered ring represent that said six membered ring has the maximum number of double bonds.

  公开了一种氢醌衍生物或其药学上可接受的盐，氢醌衍生物由式 (I) 表示： 其中 R1 是苯基，该苯基未被取代或被一个或多个各自独立选自卤素原子、C1-4 烷基和 C1-4 烷氧基的取代基取代； R2 是氢原子或 C1-4 烷基 R3 和 R4 各自独立地为氢原子或 C1-4 烷基； R5 是氢原子或 C1-4 烷基 R6、R7 和 R8 各自独立地为氢原子或 C1-4 烷基； P 是羟基 Q 是羟基、C1-4 烷氧基、C1-18 乙酰氧基或氧代基团； P 可与 Q 形成醚键； R 是羟基、C1-4 烷氧基、C1-18 乙酰氧基或氧代基团，条件是当所述 Q 和所述 R 中的一个是氧代基团时，另一个也是氧代基团； X 是单键、-NR10- 基团或-CH2-NR10- 基团，其中 R10 是氢原子或 C1-4 烷基； Y 是亚甲基或羰基；以及 六元环中的虚线键表示所述六元环具有最大数目的双键。
• Compounds for treating mitochondrial disease
  申请人：Khondrion IP B.V.

  公开号：US10815211B2

  公开（公告）日：2020-10-27

  The invention relates to novel compounds that are useful for modulating cellular ROS. The compounds are amide-derivatives of 2-hydroxy-2-methyl-4-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-butanoic acid. The compounds of the invention are formulated into pharmaceutical or cosmetic compositions. The invention further relates to methods wherein the compounds of the invention are used for treating or preventing diseases associated with increased ROS levels mitochondrial disorders and/or conditions associated with mitochondrial dysfunction, including adverse drug effects. The invention also relates to cosmetic methods for treating or delaying further aging of the skin and veterinary applications.

  本发明涉及可用于调节细胞 ROS 的新型化合物。这些化合物是 2-羟基-2-甲基-4-(3,5,6-三甲基-1,4-苯醌-2-基)-丁酸的酰胺衍生物。本发明的化合物可配制成药物或化妆品组合物。本发明进一步涉及本发明化合物用于治疗或预防与 ROS 水平升高相关的疾病线粒体紊乱和/或与线粒体功能障碍相关的病症（包括药物不良反应）的方法。本发明还涉及治疗或延缓皮肤进一步衰老的美容方法和兽医应用。
• Compounds for use in treating depression and migraine
  申请人：Khondrion IP B.V.

  公开号：US11357767B2

  公开（公告）日：2022-06-14

  The invention relates to amide-derivatives of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid for use in a treatment for preventing or suppressing symptoms associated with mood disorders, headaches and migraine. The compounds of the invention can be used to treat any subject suffering from a mood disorder, headaches and/or migraine but can specifically be used to treat a mood disorder, headaches and/or migraine in patients suffering from a mitochondrial disease.

  本发明涉及 6-羟基-2,5,7,8-四甲基苯并二氢吡喃-2-羧酸的酰胺衍生物，用于预防或抑制与情绪障碍、头痛和偏头痛相关的症状。本发明的化合物可用于治疗任何患有情绪障碍、头痛和/或偏头痛的患者，但可特别用于治疗线粒体疾病患者的情绪障碍、头痛和/或偏头痛。
• Development and Validation of Oxygen Radical Absorbance Capacity Assay for Lipophilic Antioxidants Using Randomly Methylated β-Cyclodextrin as the Solubility Enhancer
  作者：Dejian Huang、Boxin Ou、Maureen Hampsch-Woodill、Judith A. Flanagan、Elizabeth K. Deemer

  DOI：10.1021/jf0113732

  日期：2002.3.1

  We recently reported the improved oxygen radical absorbance capacity (ORAC) assay using fluorescein (FL) as the fluorescent probe. The current ORAC(FL) assay is limited in hydrophilic antioxidant due to the aqueous environment of the assay. Lipophilic antioxidants mainly include the vitamin E family and carotenoids, which play a critical role in biological defense systems. In this paper, we expanded the current ORAC(FL) assay to lipophilic antioxidants. Randomly methylated beta-cyclodextrin (RMCD) was introduced as the water solubility enhancer for lipophilic antioxidants. Seven percent RMCD (w/v) in a 50% acetone-H2O mixture was found to sufficiently solubilize vitamin E compounds and other lipophilic phenolic antioxidants in 75 mM phosphate buffer (pH 7.4). This newly developed ORAC assay (abbbreviated ORAC(FL-LIPO)) was validated through linearity, precision, accuracy, and ruggedness. The validation results demonstrate that the ORAC(FL-LIPO) assay is reliable and robust. For the first time, by using 6-hydroxy-2,5,7,8-tetramethyl-2-carboxylic acid as a standard (1.0), the ORAC values of alpha-tocopherol, (+)-gamma-tocopherol, (+)-delta-tocopherol, alpha-tocopherol acetate, tocotrienols, 2,6-di-tert-butyl-4-methylphenol, and gamma-oryzanol were determined to be 0.5 +/- 0.02, 0.74 +/- 0.03, 1.36 +/- 0.14, 0.00, 0.91 +/- 0.04, 0.16 +/- 0.01, and 3.00 +/- 0.26, respectively. The structural information of oxidized alpha-tocopherol obtained by liquid chromatography/mass spectrometry reveals that the mechanism for the reaction between the vitamin E and the peroxyl radical follows the hydrogen atom transfer mechanism, which is in agreement with the notion that vitamin E is the chain-breaking antioxidant.