DL-α-tocopheryl monomaleate | 282718-22-3

• 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: DL-α-tocopheryl monomaleate
• 英文别名: vitamin E maleate
• CAS: 282718-22-3
• 化学式: C₃₃H₅₂O₅
• 分子量: 528.773
• InChiKey: TVJDNCXEHYYXCF-JQRBHALPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.68
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  DL-α-tocopheryl monomaleate 在 benzyltrimethylazanium tribroman-2-uide 作用下， 以 四氯化碳 为溶剂， 以52%的产率得到(E)-4-oxo-4-(((R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl)oxy)but-2-enoic acid
  参考文献：
  名称：

  维生素C衍生化合物在小鼠C6胶质瘤细胞中的抗癌活性

  摘要：

  合成了一个小型维生素E类似物文库，该文库具有一个通过酰胺，醚或酯键与苯并二氢吡喃核连接的游离酸基，并评估了它们对C6鼠神经胶质瘤细胞的抗癌能力。几种化合物显示出比替莫唑胺更好的抗肿瘤活性，替莫唑胺是治疗神经胶质瘤最常用的药物。

  DOI：

  10.1002/cmdc.200900492
• 作为产物：
  描述：

  马来酸酐 、 天然维生素E 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 DL-α-tocopheryl monomaleate
  参考文献：
  名称：

  维生素C衍生化合物在小鼠C6胶质瘤细胞中的抗癌活性

  摘要：

  合成了一个小型维生素E类似物文库，该文库具有一个通过酰胺，醚或酯键与苯并二氢吡喃核连接的游离酸基，并评估了它们对C6鼠神经胶质瘤细胞的抗癌能力。几种化合物显示出比替莫唑胺更好的抗肿瘤活性，替莫唑胺是治疗神经胶质瘤最常用的药物。

  DOI：

  10.1002/cmdc.200900492

文献信息

• Vitamin E derivatives
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：US06387882B1

  公开（公告）日：2002-05-14

  The present invention provides novel vitamin E derivatives represented by the following formula (I) wherein: R1 and R2 are the same or different and each denotes hydrogen or methyl, R3 denotes an S-linked SH compound (glutathione, &ggr;-glutamylcysteine, cysteine, penicillamine, an ester thereof or cysteamine), and R4 denotes hydroxyl, a N-substituted amino acid (glycine, &bgr;-alanine, &ggr;-aminobutyric acid, 5-aminovaleric acid, &egr;-aminocaproic acid, anthranilic acid, tranexamic acid, proline, an ester thereof, aminoethylsulfonic acid , aminoethylsulfinic acid) or serotonin, or a pharmacologically acceptable salt thereof, which are useful as hepatopathy suppressing agents, anticataract agents, cerebral metabolism improving agents, antioxidants and cosmetic components.

  本发明提供了以下式(I)所表示的新型维生素E衍生物，其中：R1和R2相同或不同，每个代表氢或甲基，R3代表S-连接的SH化合物（谷胱甘肽、γ-谷氨酰半胱氨酸、半胱氨酸、青霉胺、其酯或半胱胺），R4代表羟基、N-取代氨基酸（甘氨酸、β-丙氨酸、γ-氨基丁酸、5-氨基戊酸、ε-氨基己酸、间苯二酸、氨甲基巯基磺酸、氨基乙基亚砜酸）或5-羟色胺，或其药理学上可接受的盐，这些衍生物可用作抑制肝病的药剂、抗白内障剂、改善脑代谢的剂、抗氧化剂和化妆品成分。
• Self-assembled nanoparticles of modified-chitosan conjugates for the sustained release of dl-α-tocopherol
  作者：Javier Pérez Quiñones、Kurt Vesterager Gothelf、Jørgen Kjems、Chuanxu Yang、Angeles María Heras Caballero、Claudia Schmidt、Carlos Peniche Covas

  DOI：10.1016/j.carbpol.2012.10.005

  日期：2013.1

  Synthetic 06-succinylated chitosan and commercial glycol chitosan were covalently linked to DL-alpha-tocopheryl monoesters for controlled release of vitamin E. These conjugates formed self-assembled nanoparticles in aqueous solution with 254-496 nm mean diameters and DL-alpha-tocopherol contents between 27 and 39% (w/w). The particles appeared as 40-75 nm almost spherical nanoparticles when studied by scanning and transmission electron microscopy upon drying. Drug linking to chitosan matrix was confirmed by FTIR spectroscopy and proton NMR. Conjugates were also characterized by differential scanning calorimetry and wide-angle X-ray diffraction. In vitro tocopherol release studies performed in water at acid pH indicated a drug release dependence on drug content, hydrated particle sizes and employed chitosan derivative. Almost constant release rates were observed the first 7 h. The obtained nanoparticles exhibited radical scavenging activity in DPPH essay. The potential of these nanoparticles was also demonstrated by the enhancement of HMVEC cell proliferation. (C) 2012 Elsevier Ltd. All rights reserved.