13-hydroxystearic acid methyl ester trimethylsilyl ether | 55976-18-6

• 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: 13-hydroxystearic acid methyl ester trimethylsilyl ether
• 英文别名: methyl 13-trimethylsilyloxyoctadecanoate；Methyl 13-OH-octadecanoat-OTMS；Methyl 13-trimethylsilyloxy-stearate
• CAS: 55976-18-6
• 化学式: C₂₂H₄₆O₃Si
• 分子量: 386.691
• InChiKey: ZSYWADXRSSUBPG-UHFFFAOYSA-N

物化性质

• 沸点：
  415.4±18.0 °C(Predicted)
• 密度：
  0.883±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  13(s)-氢过氧基-(9z,11e,15z)-十八三烯酸 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

文献信息

• Characterization and Quantification of Free and Esterified 9- and 13-Hydroxyoctadecadienoic Acids (HODE) in Barley, Germinating Barley, and Finished Malt
  作者：Holger Hübke、Leif-Alexander Garbe、Roland Tressl

  DOI：10.1021/jf048490s

  日期：2005.3.1

  glycolipids, etc.) in barley, germinating barley, and finished malt was performed using [13-(18)O(1)]-(S)-13-HODE isotope dilution assays with GC-MS and straight- and chiral-phase HPLC. 9- and 13- HODE occur approximately racemically in barley, indicating an autoxidation. The enantiomeric excesses increase to 78% S for free 9-HODE and to 58% S for free 13-HODE in germinating barley as a result of lipoxygenase-2

  （R）-9-和（S）-9-羟基-10E，12Z-十八碳二烯酸以及（R）-13-和（S）-13-羟基-9Z，11E-十八碳二烯酸（HODE ）作为游离酸，在大麦，发芽的大麦和成品麦芽中，用[13-（18）O（1）]-在大麦，发芽的大麦和成品麦芽中在三酰基甘油（存储脂质）中酯化，并在极性脂质（磷脂，糖脂等）中酯化。 （S）-13-HODE同位素稀释分析，采用GC-MS以及直相和手性HPLC。9-和13- HODE在大麦中大约消旋地发生，表明存在自氧化作用。由于脂氧合酶-2（LOX-2）催化，发芽大麦中的对映体过量对游离的9-HODE增加到78％S，对游离的13-HODE增加到58％S，但是游离HODE处于低浓度。大麦和麦芽中超过90％的HODE被酯化。在绿色麦芽的储存中，检测到53 mg / kg 9-HODE和147 mg / kg 13-HODE的脂质。30:70的比率反映了麦芽中LOX-
• Soybean Lipoxygenase-Mediated Oxygenation of Monounsaturated Fatty Acids to Enones
  作者：Charles H. Clapp、Susan E. Senchak、Theodore J. Stover、Thomas C. Potter、Peter M. Findeis、Mark J. Novak

  DOI：10.1021/ja0032071

  日期：2001.1.1
• GULACAR, FAZIL O.;BUCHS, ARMAND;SUSINI, ALBERTO, J. CHROMATOGR., 479,(1989) N, C. 61-72
  作者：GULACAR, FAZIL O.、BUCHS, ARMAND、SUSINI, ALBERTO

  DOI：——

  日期：——
• Thermal conversions of trimethylsilyl peroxides of linoleic and linolenic acids
  作者：Alexander N. Grechkin、Lucia S. Mukhtarova、Mats Hamberg

  DOI：10.1016/j.chemphyslip.2005.09.001

  日期：2005.12

  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.