cholesteryl 9-hydroperoxyoctadeca-trans-10,trans-12-dienoate | 176300-84-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl 9-hydroperoxyoctadeca-trans-10,trans-12-dienoate
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (10E,12E)-9-hydroperoxyoctadeca-10,12-dienoate
• CAS: 176300-84-8
• 化学式: C₄₅H₇₆O₄
• 分子量: 681.096
• InChiKey: PJEDIANARLMFBK-LYBKVHSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  49
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cholesteryl 9-hydroperoxyoctadeca-trans-10,trans-12-dienoate 在 三苯基膦 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 Methyl 9-hydroxy-trans-10,trans-12-octadecadienoat
  参考文献：
  名称：

  Identification and Quantification of the Regioisomeric Cholesteryl Linoleate Hydroperoxides in Oxidized Human Low Density Lipoprotein and High Density Lipoprotein

  摘要：

  Oxidation of human LDL is implicated as an initiatior of atherosclerosis. Isolated low density lipoprotein (LDL) and high density lipoprotein (HDL(2)) were exposed to aqueous radicals generated from the thermolabile azo compound 2,2'-azobis(2-amidinopropane) dihydeochloride. The primary nonpolar lipid products formed from the autoxidation of LDL and HDL were the regioisomeric cholesteryl linoleate hydroperoxides. In LDL oxidations, 9- and 13-hydroperoxides with trans,cis conjugated diene were formed as the major oxidation products if endogenous a-tocopherol was present in the LDL. After extended oxidation of LDL, at the time when endogenous a-tocopherol was consumed, the two trans,cis conjugated diene hydroperoxides began to disappear and the 9- and 13-hydroperoxides with trans,trans conjugated diene appeared. At very long oxidation times, none of the primary products, the conjugated diene hydroperoxides, were present. In HDL(2), which has only very low levels of antioxidants, both the 9- and 13-hydroperoxides with trans,cis conjugated diene and the 9- and 13-hydroperoxides with trans,trans conjugated diene were formed at early stages of oxidation. The corresponding alcohols were also formed in the HDL(2) oxidations. A mechanistic hypothesis consistent with these observations is presented.

  DOI：

  10.1021/tx9600098
• 作为产物：
  描述：

  胆甾醇亚油酸酯 在 氧气 、 反式-二叔丁基连二次硝酸酯 作用下， 以 苯 为溶剂， 以17.2%的产率得到cholesterol 13-hydroperoxy-cis-9,trans-11-octadecadienoate
  参考文献：
  名称：

  Identification and Quantification of the Regioisomeric Cholesteryl Linoleate Hydroperoxides in Oxidized Human Low Density Lipoprotein and High Density Lipoprotein

  摘要：

  Oxidation of human LDL is implicated as an initiatior of atherosclerosis. Isolated low density lipoprotein (LDL) and high density lipoprotein (HDL(2)) were exposed to aqueous radicals generated from the thermolabile azo compound 2,2'-azobis(2-amidinopropane) dihydeochloride. The primary nonpolar lipid products formed from the autoxidation of LDL and HDL were the regioisomeric cholesteryl linoleate hydroperoxides. In LDL oxidations, 9- and 13-hydroperoxides with trans,cis conjugated diene were formed as the major oxidation products if endogenous a-tocopherol was present in the LDL. After extended oxidation of LDL, at the time when endogenous a-tocopherol was consumed, the two trans,cis conjugated diene hydroperoxides began to disappear and the 9- and 13-hydroperoxides with trans,trans conjugated diene appeared. At very long oxidation times, none of the primary products, the conjugated diene hydroperoxides, were present. In HDL(2), which has only very low levels of antioxidants, both the 9- and 13-hydroperoxides with trans,cis conjugated diene and the 9- and 13-hydroperoxides with trans,trans conjugated diene were formed at early stages of oxidation. The corresponding alcohols were also formed in the HDL(2) oxidations. A mechanistic hypothesis consistent with these observations is presented.

  DOI：

  10.1021/tx9600098