(3beta)-胆甾-5-烯-3-醇 (9Z,11E)-13-羟基-9,11-十八碳二烯酸酯 | 167354-91-8

• 物质功能分类: 生物 - 生化试剂盒
• 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
• 中文名称: (3beta)-胆甾-5-烯-3-醇 (9Z,11E)-13-羟基-9,11-十八碳二烯酸酯
• 中文别名: (+/-)-13-羟基-9Z,11E-十八碳二烯酸,胆酯基酯；(3beta)-胆甾-5-烯-3-醇(9Z,11E)-13-羟基-9,11-十八碳二烯酸酯
• 英文名称: cholesteryl 13-hydroxyoctadeca-cis-9,trans-11-dienoate
• 英文别名: (+/-)13-HODE cholesteryl ester；[(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-hydroxyoctadeca-9,11-dienoate
• CAS: 167354-91-8
• 化学式: C₄₅H₇₆O₃
• 分子量: 665.097
• InChiKey: RZXYPSUQZUUHPD-ZCNQQENXSA-N

物化性质

• 沸点：
  707.1±53.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：>50mg/mL； DMSO：>50mg/mL；乙醇：>50mg/mL；乙醇:PBS (1:10): <10 μg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium methylate 、 (3beta)-胆甾-5-烯-3-醇 (9Z,11E)-13-羟基-9,11-十八碳二烯酸酯 以 甲醇 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：

  cholesterol 13-hydroperoxy-cis-9,trans-11-octadecadienoate 在 三苯基膦 作用下， 以 乙醚 为溶剂， 生成 (3beta)-胆甾-5-烯-3-醇 (9Z,11E)-13-羟基-9,11-十八碳二烯酸酯
  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

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.