methyl (9Z,11E,13S)-13-trimethylsilyloxyoctadeca-9,11-dienoate | 130607-65-7

• 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)-13-trimethylsilyloxyoctadeca-9,11-dienoate
• CAS: 130607-65-7
• 化学式: C₂₂H₄₂O₃Si
• 分子量: 382.659
• InChiKey: CKJJXCPHFROKCV-IYQRKSMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  26.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (9Z,11E,13S)-13-trimethylsilyloxyoctadeca-9,11-dienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以83%的产率得到(9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid methyl ester
  参考文献：
  名称：

  有效合成13（S）-羟基-9Z，11E-十八碳二烯酸（coriolic）酸。

  摘要：

  描述了一种高效且高度选择性的13（S）-羟基-9Z，11E十八碳二烯酸（coolaolic）的全合成反应，该反应是从容易通过对映选择性酶水解获得的旋光性乳糖醇开始的。

  DOI：

  10.1016/0040-4039(90)80129-a
• 作为产物：
  描述：

  9-溴-1-壬醇 在 溴 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙腈 为溶剂， 生成 methyl (9Z,11E,13S)-13-trimethylsilyloxyoctadeca-9,11-dienoate
  参考文献：
  名称：

  有效合成13（S）-羟基-9Z，11E-十八碳二烯酸（coriolic）酸。

  摘要：

  描述了一种高效且高度选择性的13（S）-羟基-9Z，11E十八碳二烯酸（coolaolic）的全合成反应，该反应是从容易通过对映选择性酶水解获得的旋光性乳糖醇开始的。

  DOI：

  10.1016/0040-4039(90)80129-a

文献信息

• Production of Hydroxy Unsaturated Fatty Acids Using Crude Lipoxygenase Obtained from Infected Rice Plants
  作者：Tadahiro Kato、Tsutomu Watanabe、Toshifumi Hirukawa、Norihiro Tomita、Tsuneo Namai

  DOI：10.1246/bcsj.69.1663

  日期：1996.6

  In order to explore the oxidation mode of lipoxygenase (LOX) obtained from infected rice plants, typical unsaturated fatty acids (3—8) were treated with LOX and oxygen. It was observed that ω-10 and ω-6 positions of unsaturated fatty acids were oxidized predominantly in the cases of exotic ω-6 (4 and 5) and ω-3 (7 and 8) series, respectively. In the case of endogenous fatty acids (3 and 6), oxidation at ω-6 position predominated. All the allylic alcohols obtained by reduction of the oxidation products with NaBH4 possess S-configuration.

  为了探索从感染的水稻植物中获得的脂氧化酶（LOX）的氧化模式，通过LOX和氧气处理了典型的不饱和脂肪酸（3—8）。观察到在异源ω-6（4和5）和ω-3（7和8）系列的不饱和脂肪酸中，主要在ω-10和ω-6位发生氧化。而在内源性脂肪酸（3和6）的情况下，ω-6位的氧化占主导地位。通过用NaBH4还原氧化产物获得的所有烯丙醇均具有S构型。
• 9-Hydroxy-10,12-octadecadienoic acid (9-HODE) and 13-hydroxy-9,11-octadecadienoic acid (13-HODE): excellent markers for lipid peroxidation
  作者：Peter Spiteller、Gerhard Spiteller

  DOI：10.1016/s0009-3084(97)00070-4

  日期：1997.10

  Various conditions for conversion of (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9S-HPODE) and (13S,92,10E)-13-hydroperoxy-9,11-octadecadienoic acid (13S-HPODE) into the corresponding hydroxy acids, (9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid (9S-HODE) and (13S,9Z,10E)-13-hydroxy-9,11-octadecadienoic acid (13S-HODE), were investigated in vitro. 9S-HODE and 13S-HODE were subjected to lipid peroxidation under various conditions: oxidation was carried out in air only, and in air/Fe2+/ascorbate, air/H2O2/Fe2+, air/Fe2+, and air/Fe3+. In contrast to the corresponding hydroperoxides (9S-HPODE and 13S-HPODE), 9-HODE and 13-HODE proved to be stable in all these oxidation experiments. Unexpectedly, hydroxy compounds obtained by reduction of hydroperoxides derived from arachidonic acid were not attacked by air/Fe2+/ascorbate or air/Fe2+. Thus, for instance, (15S,5Z,8Z,11Z,13E)-15-hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE) remained unchanged in spite of possessing the structural prerequisites for attack by radicals, i.e. a CH2-group located between two double bonds. Consequently, metal-induced air oxidation reactions of these systems seem to be restricted to hydroperoxides of unsaturated acids (LOOH) and not to corresponding hydroxy compounds (LOH). The reported experiments explain why hydroxy derivatives of unsaturated acids, especially 9-HODE and 13-HODE, are enriched in naturally occurring lipid peroxidation (LPO) processes to a greater extent than any other LPO product and why they are nearly ideal markers for LPO. (C) 1997 Elsevier Science Ireland Ltd.
• BLOCH, ROBERT;PERFETTI, MARIE-THERESE, TETRAHEDRON LETT., 31,(1990) N8, C. 2577-2580
  作者：BLOCH, ROBERT、PERFETTI, MARIE-THERESE

  DOI：——

  日期：——