11-selenadodecyl-2,3-O-isopropylideneglycerylether | 264617-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-selenadodecyl-2,3-O-isopropylideneglycerylether
• 英文别名: 11-selenadodecyl-2,3-isopropylideneglycerylether
• CAS: 264617-30-3
• 化学式: C₁₇H₃₄O₃Se
• 分子量: 365.415
• InChiKey: CXYIZQDZCMYSOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  21.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  11-selenadodecyl-2,3-O-isopropylideneglycerylether 在 盐酸 、 CAB lipase 作用下， 以 甲醇 、 萘烷 为溶剂， 35.0~80.0 ℃ 、1.33 kPa 条件下， 反应 145.0h， 生成 1-(11-selenadodecyl)-3-(β-apo-8'-carotenoyl)glycerol
  参考文献：
  名称：

  Synthesis of structured lipids and etherlipids with antioxidants: combination of a selena fatty acid and a selena fatty alcohol with a carotenoic acid in glyceride molecules

  摘要：

  Selenium and carotenoids show similar and complementary properties and protect against a variety of pathological processes. Mixtures of both compounds are found in nutritional supplements and are used to prevent several diseases. The synthetic connection of carotenoids with selenium in glycerols may increase the chemopreventive activity of the individual compounds. beta-Apo-8'-carotenoic acid and 7-selenacapryloic acid were esterified with glycerol to highly unsaturated stable di- and triglycerides. Intramolecular selenium:carotenoid ratios of 1:1, 2:1 and 1:2 were obtained for 1-(7-selenaoctanoyl)-3-(beta-apo-8'-carotenoyl)glycerol, 1,3-di-(beta-apo-8'-carotenoyl)-2-(7-selenaoctanoyl)-glycerol and 1,2-di-(7-selenaoctanoyl)-3-(beta-apo-8'-carotenoyl)-glycerol, respectively. The carotenoic acid was likewise connected to the pharmacologically interesting 11-selenalaurylglycerolether forming an alkyl-acylglyceride: 1-(11-selenadodecyl)-3-(beta-apo-8'-carotenoyl)-glycerol. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(99)00137-1
• 作为产物：
  描述：

  11-selenadodecanol 在 氢氧化钾 、 三乙胺 作用下， 以 二氯甲烷 、 xylene 为溶剂， 生成 11-selenadodecyl-2,3-O-isopropylideneglycerylether
  参考文献：
  名称：

  Synthesis of structured lipids and etherlipids with antioxidants: combination of a selena fatty acid and a selena fatty alcohol with a carotenoic acid in glyceride molecules

  摘要：

  Selenium and carotenoids show similar and complementary properties and protect against a variety of pathological processes. Mixtures of both compounds are found in nutritional supplements and are used to prevent several diseases. The synthetic connection of carotenoids with selenium in glycerols may increase the chemopreventive activity of the individual compounds. beta-Apo-8'-carotenoic acid and 7-selenacapryloic acid were esterified with glycerol to highly unsaturated stable di- and triglycerides. Intramolecular selenium:carotenoid ratios of 1:1, 2:1 and 1:2 were obtained for 1-(7-selenaoctanoyl)-3-(beta-apo-8'-carotenoyl)glycerol, 1,3-di-(beta-apo-8'-carotenoyl)-2-(7-selenaoctanoyl)-glycerol and 1,2-di-(7-selenaoctanoyl)-3-(beta-apo-8'-carotenoyl)-glycerol, respectively. The carotenoic acid was likewise connected to the pharmacologically interesting 11-selenalaurylglycerolether forming an alkyl-acylglyceride: 1-(11-selenadodecyl)-3-(beta-apo-8'-carotenoyl)-glycerol. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(99)00137-1

文献信息

• 11-selenadodecylglyceryl-1-ether in lipid autoxidation
  作者：N. Yanishlieva、V. Raneva、E. Marinova、H. Houte、V. Partali、H. -R. Sliwka

  DOI：10.1007/s11746-001-0327-7

  日期：2001.7

  AbstractThe effect of 11‐selenadodecylglyceryl‐1‐ether (11‐SeDGE) at concentrations of 5 × 10−4 and 1 × 10−2 M on the autoxidation of sunflower oil with a natural content of 0.06% tocopherols at 100°C and at room temperature in the dark and of pure triacylglycerols of sunflower oil (TGSO) at 100°C was studied. The process was followed by peroxide concentration (peroxide value) determination and by ultraviolet (UV) spectroscopy. It was found that 11‐SeDGE acted synergistically with the tocopherols in sunflower oil in a dose‐dependent manner to delay oxidation at 100°C. The results from the UV spectra indicated that 11‐SeDGE decomposed the initiators of the process, the hydroperoxides, into inactive products. During oxidation of pure TGSO (i.e, depleted of tocopherols) at 100°C, 11‐SeDGE retarded the process without a pronounced induction period. At room temperature, 11‐SeDGE showed a slight prooxidative effect on sunflower oil oxidation. Taking into account the established prooxidative effect of the two hydroxy groups in a molecule such as 11‐SeDGE, it was recommended to study the lipid autoxidation in the presence of selenium compounds that do not contain such prooxidative groups.