cholesterol 13-hydroperoxy-cis-9,trans-11-octadecadienoate | 167354-92-9

• 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: cholesterol 13-hydroperoxy-cis-9,trans-11-octadecadienoate
• 英文别名: cholesteryl 13-hydroperoxyoctadeca-cis-9,trans-11-dienoate；[(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] (9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoate
• CAS: 167354-92-9
• 化学式: C₄₅H₇₆O₄
• 分子量: 681.096
• InChiKey: GXHCTYFXBSGOGT-ZCNQQENXSA-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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  胆甾醇亚油酸酯	cholesterol linoleate	604-33-1	C45H76O2	649.097

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  (3beta)-胆甾-5-烯-3-醇 (9Z,11E)-13-羟基-9,11-十八碳二烯酸酯	cholesteryl 13-hydroxyoctadeca-cis-9,trans-11-dienoate	167354-91-8	C45H76O3	665.097

反应信息

• 作为反应物：
  描述：

  cholesterol 13-hydroperoxy-cis-9,trans-11-octadecadienoate 在 三苯基膦 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 methyl coriolate
  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 、 亚甲兰 作用下， 以 正己烷 、 异丙醇 为溶剂， 反应 5.0h， 生成 cholesterol 10-hydroperoxy-trans-8,cis-12-octadecadienoate 、 cholesterol 9-hydroperoxy-trans-10,cis-12-octadecadienoate 、 cholesterol 13-hydroperoxy-cis-9,trans-11-octadecadienoate 、 cholesterol 12-hydroperoxy-cis-9,trans-13-octadecadienoate
  参考文献：
  名称：

  Preparation of fatty acid cholesterol ester hydroperoxides by photosensitized oxidation

  摘要：

  Preparation of fatty acid cholesterol ester hydroperoxides was undertaken with the purpose of evaluating their biological effects on cell growth. Cholesterol stearate, oleate, linoleate and alpha-linolenate were oxidized using methylene blue as a photosensitizer. The structures of all compounds were established by mass spectrometry and by nuclear magnetic resonance. The photosensitized oxidation of cholesterol oleate gave two hydroperoxide isomers: 9-hydroperoxy-trans-10-octadecenoate, and 10-hydroperoxy-trans-8-octadecenoate. In the case of the cholesterol linoleate, hydroperoxide isomers formed were: 9-hydroperoxy-trans-10, cis-12-octadecadienoate; 10-hydroperoxy-trans-8, cis-12-octadecadienoate; 12-hydroperoxy-cis-9, trans-13-octadecadienoate; 13-hydroperoxy-cis-9, trans-11-octadecadienoate. The oxidation of the cholesterol alpha-linolenate gave a mixture of six hydroperoxide isomers, at positions 9, 10, 12, 13, 15 and 16 of the fatty acid chain. The photosensitized oxidation of cholesterol stearate produced a formation of hydroperoxide at position 5 alpha of cholesterol. The same hydroperoxide isomers on the fatty acid chain were obtained as described in the literature for the fatty acid methyl esters. (C) 1999 Published by Elsevier Science ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(99)00049-3

文献信息

• Preparation of fatty acid cholesterol ester hydroperoxides by photosensitized oxidation
  作者：M El Hafidi、F Michel、J Bascoul、A Crastes de Paulet

  DOI：10.1016/s0009-3084(99)00049-3

  日期：1999.7

  Preparation of fatty acid cholesterol ester hydroperoxides was undertaken with the purpose of evaluating their biological effects on cell growth. Cholesterol stearate, oleate, linoleate and alpha-linolenate were oxidized using methylene blue as a photosensitizer. The structures of all compounds were established by mass spectrometry and by nuclear magnetic resonance. The photosensitized oxidation of cholesterol oleate gave two hydroperoxide isomers: 9-hydroperoxy-trans-10-octadecenoate, and 10-hydroperoxy-trans-8-octadecenoate. In the case of the cholesterol linoleate, hydroperoxide isomers formed were: 9-hydroperoxy-trans-10, cis-12-octadecadienoate; 10-hydroperoxy-trans-8, cis-12-octadecadienoate; 12-hydroperoxy-cis-9, trans-13-octadecadienoate; 13-hydroperoxy-cis-9, trans-11-octadecadienoate. The oxidation of the cholesterol alpha-linolenate gave a mixture of six hydroperoxide isomers, at positions 9, 10, 12, 13, 15 and 16 of the fatty acid chain. The photosensitized oxidation of cholesterol stearate produced a formation of hydroperoxide at position 5 alpha of cholesterol. The same hydroperoxide isomers on the fatty acid chain were obtained as described in the literature for the fatty acid methyl esters. (C) 1999 Published by Elsevier Science ireland Ltd. All rights reserved.
• Identification and Quantification of the Regioisomeric Cholesteryl Linoleate Hydroperoxides in Oxidized Human Low Density Lipoprotein and High Density Lipoprotein
  作者：James A. Kenar、Christine M. Havrilla、Ned A. Porter、John R. Guyton、Spencer A. Brown、Keith F. Klemp、Elizabeth Selinger

  DOI：10.1021/tx9600098

  日期：1996.1.1

  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.