O¹-(8'-apo-β-apo-caroten-8'-oyl)-O²-[6-(methylselanyl)hexanoyl]glycerol | 375396-51-3

• 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: O¹-(8'-apo-β-apo-caroten-8'-oyl)-O²-[6-(methylselanyl)hexanoyl]glycerol
• 英文别名: 1-(β-apo-8'-carotenoyl)-2-(7-selenaoctanoyl)glycerol；[3-hydroxy-2-(6-methylselanylhexanoyloxy)propyl] (2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenoate
• CAS: 375396-51-3
• 化学式: C₄₀H₅₈O₅Se
• 分子量: 697.858
• InChiKey: ISTHGXFESIIVJL-CWSSIOODSA-N

物化性质

• 沸点：
  755.3±39.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  46
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  奎诺二甲基丙烯酸酯 、 O¹-(8'-apo-β-apo-caroten-8'-oyl)-O²-[6-(methylselanyl)hexanoyl]glycerol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以24%的产率得到1-(β-apo-8'-carotenoyl)-2-(7-selenaoctanoyl)-3-(6-hydroxy-2,5,7,8-tetramethylchroman-2-acyl)-glycerol
  参考文献：
  名称：

  Synthesis of a triantioxidant compound: combination of β-apo-8′-carotenoic acid, selenacapryloic acid and trolox in a triglyceride

  摘要：

  Carotenoids, vitamin-E and selenium show similar or complementary physiological properties and protect against a variety of pathological processes. Mixtures of these antioxidants are found in nutritional supplements and are used to prevent several diseases. The synthetic connection of carotenoids, vitamin-E and selenium may increase the chemopreventive activity of the individual compounds. A carotenoic acid, a selena fatty acid and the vitamin-E derivative trolox were successively esterified with glycerol to 1-(beta -apo-8'carotenoyl)-2-(7-selenaoctanoyl)-3-(6-hydroxy-2,5,7,8--tetramethylchroman-2-acyl)-glycerol. This triantioxidant compound revealed, in the DPPH (1,1-diphenyl-2-picrylhydrazyl) test, an additive effect, consisting of the radical quenching activity of the carotenoid and trolox. The DPPH test was not sensitive for the Se moiety in the triantioxidant compound. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00164-5
• 作为产物：
  描述：

  2-(7-selenaoctanoyl)-1,3-benzylideneglycerol 在 吡啶 、 硼酸三乙酯 、 硼酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 O¹-(8'-apo-β-apo-caroten-8'-oyl)-O²-[6-(methylselanyl)hexanoyl]glycerol
  参考文献：
  名称：

  Synthesis of a triantioxidant compound: combination of β-apo-8′-carotenoic acid, selenacapryloic acid and trolox in a triglyceride

  摘要：

  Carotenoids, vitamin-E and selenium show similar or complementary physiological properties and protect against a variety of pathological processes. Mixtures of these antioxidants are found in nutritional supplements and are used to prevent several diseases. The synthetic connection of carotenoids, vitamin-E and selenium may increase the chemopreventive activity of the individual compounds. A carotenoic acid, a selena fatty acid and the vitamin-E derivative trolox were successively esterified with glycerol to 1-(beta -apo-8'carotenoyl)-2-(7-selenaoctanoyl)-3-(6-hydroxy-2,5,7,8--tetramethylchroman-2-acyl)-glycerol. This triantioxidant compound revealed, in the DPPH (1,1-diphenyl-2-picrylhydrazyl) test, an additive effect, consisting of the radical quenching activity of the carotenoid and trolox. The DPPH test was not sensitive for the Se moiety in the triantioxidant compound. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00164-5