methyl (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate | 90079-46-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
• CAS: 90079-46-2
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: BYBABUPPOWFKIP-GOSIXVIOSA-N

物化性质

• 沸点：
  447.3±45.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  methyl (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate 在 platinum(IV) oxide 吡啶 、 氢气 、 六甲基二硅氮烷 作用下， 以 乙醚 为溶剂， 反应 0.17h， 生成 13-hydroxystearic acid methyl ester trimethylsilyl ether
  参考文献：
  名称：

  Thermal conversions of trimethylsilyl peroxides of linoleic and linolenic acids

  摘要：

  The trimethylsilyl (TMS) peroxides/esters of the fatty acid hydroperoxides (9S, 10E, 12Z)-9-hydroperoxy- 10, 12-octadecadienoic acid (9-HPOD) and (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid (13-HPOT) were subjected to gas chromatography-mass spectrometry and products formed by thermal rearrangements were identified. The main products were decadienals and the TMS derivatives of 13-oxo-9,1 1-tridecadienoic acid, epoxyalcohols, hemiacetals, and ketodienes. Oxy radicals as well as epoxyallylic radicals served as intermediates in the formation of these compounds. The thermal TMS peroxide conversions documented provided biomimetic models for enzymatic conversions of fatty acid hydroperoxides and also offered a method to generate an array of oxylipin derivatives of value as reference compounds in GC-MS studies. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.09.001
• 作为产物：
  描述：

  重氮甲烷 、 13(s)-氢过氧基-(9z,11e,15z)-十八三烯酸 生成 methyl (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
  参考文献：
  名称：

  Thermal conversions of trimethylsilyl peroxides of linoleic and linolenic acids

  摘要：

  The trimethylsilyl (TMS) peroxides/esters of the fatty acid hydroperoxides (9S, 10E, 12Z)-9-hydroperoxy- 10, 12-octadecadienoic acid (9-HPOD) and (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid (13-HPOT) were subjected to gas chromatography-mass spectrometry and products formed by thermal rearrangements were identified. The main products were decadienals and the TMS derivatives of 13-oxo-9,1 1-tridecadienoic acid, epoxyalcohols, hemiacetals, and ketodienes. Oxy radicals as well as epoxyallylic radicals served as intermediates in the formation of these compounds. The thermal TMS peroxide conversions documented provided biomimetic models for enzymatic conversions of fatty acid hydroperoxides and also offered a method to generate an array of oxylipin derivatives of value as reference compounds in GC-MS studies. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.09.001

文献信息

• Iron(III) and copper(II) catalysed transformations of fatty acid hydroperoxides: efficient generation of peroxy radicals with copper(II) trifluoromethanesulphonate
  作者：Richard K. Haynes、Simone C. Vonwiller

  DOI：10.1039/c39900001102

  日期：——

  dietherate into epoxy alcohols and chloroepoxides, catalytic amounts of copper(II) trifluoromethanesulphonate in the presence of octanoic acid under oxygen efficiently convert the second compound into hydroperoxy dioxolanes and dioxabicycloheptanes, and methyl (5Z,8Z,11Z,13E,15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate (15-HPETE methyl ester, 18) into hydroperoxy bisdioxolanes via an 11-peroxy radical

  而甲基（9 Z，11 E，13 S）-13-hydroperoxyoctadeca-9,11-dinoate（3）和甲基（9 Z，11 E，13 S，15 Z）-13-hydroperoxyoctadeca-9,11，15 -三烯酸酯（4）被FeCl 3二醚酸酯转化为环氧醇和氯环氧化物，催化量的三氟甲磺酸铜（II）在辛酸的存在下，在氧气下有效地将第二种化合物转化为氢过氧二氧戊环和二氧杂双环庚烷，以及甲基（5 Z， 8 Z，11 Z，13 E，15S）-15-氢过氧双酚-5,8,11,13-四烯酸酯（15-HPETE甲酯，18）通过11-过氧自由基变成氢过氧双二氧戊环。
• HAYNES, RICHARD K.;VONWILLER, SIMONE C., J. CHEM. SOC. CHEM. COMMUN.,(1990) N6, C. 1102-1104
  作者：HAYNES, RICHARD K.、VONWILLER, SIMONE C.

  DOI：——

  日期：——