13-hydroxy-9,11-octadecadienoic acid | 5204-88-6

• 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-hydroxy-9,11-octadecadienoic acid
• 英文别名: 13-hydroxy-9,13-octadecadienoic acid；13-hydroxyoctadeca-9,11-dienoic acid；coriolic acid；13-HODE；13-Hydroxy-9,11-octadecadiensaeure
• CAS: 5204-88-6
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: HNICUWMFWZBIFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 13-hydroxy-9,11-octadecadienoic acid 在 chromium(VI) oxide 作用下， 生成 methyl 13-oxooctadeca-9,11-dienoate
  参考文献：
  名称：

  由脂质氢过氧化物及其二级和三级氧化产物引发的苯丙氨酸降解的模型研究。

  摘要：

  13-氢过氧十八烷基-9,11-二烯酸甲酯（MeLOOH），13-氢过氧十八烷基-9,11,15-三烯酸甲酯（MeLnOOH），13-羟基十八烷基-9,11-二烯酸甲酯（MeLOH），13-甲基含苯丙氨酸的oxooctadeca-9,11-dienoate（MeLCO），9,10-环氧13-hydroxy-11-octadecenoate甲基（MeLEPOH）和9,10-环氧13-oxo-11-octadecenoate甲基（MeLEPCO）与苯丙氨酸为了确定在氨基酸的Strecker降解中一级，二级和三级脂质氧化产物的比较反应性，我们进行了研究。尽管脂质反应性按以下顺序略有降低，但所有测定的脂质都能够高度降解氨基酸：MeLEPCO>或= MeLCO> MeLEPOH>或= MeLOH> MeLOOH大约= MeLnOOH。这些数据证实了许多脂质氧化产物具有通过Strecker型机制降解氨

  DOI：

  10.1021/jf801409w
• 作为产物：
  描述：

  9-羟基正壬酸甲酯 在 lithium hydroxide 、 2,2'-联喹啉 、 4 A molecular sieve 、 环己胺 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 13-hydroxy-9,11-octadecadienoic acid
  参考文献：
  名称：

  New functionalized Horner-Wadsworth-Emmons reagents: useful building blocks in the synthesis of polyunsaturated aldehydes. A short synthesis of (.+-.)-(E,E)-coriolic acid

  摘要：

  DOI：

  10.1021/jo00306a006

文献信息

• A non-canonical caleosin from<i>Arabidopsis</i>efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity
  作者：Elizabeth Blée、Martine Flenet、Benoît Boachon、Marie-Laure Fauconnier

  DOI：10.1111/j.1742-4658.2012.08757.x

  日期：2012.10

  In plants, epoxygenated fatty acids (EFAs) are constituents of oil seeds as well as defence molecules and components of biopolymers (cutin, suberin). While the pleiotropic biological activities of mammalian EFAs have been well documented, there is a paucity of information on the physiological relevance of plant EFAs and their biosynthesis. Potential candidates for EFA formation are caleosin‐type peroxygenases which catalyze the epoxidation of unsaturated fatty acids in the presence of hydroperoxides as co‐oxidants. However, the caleosins characterized so far, which are mostly localized in seeds, are poor epoxidases. In sharp contrast, quantitative RT‐PCR analysis revealed that PXG4, a class II caleosin gene, is expressed in roots, stems, leaves and flowers of Arabidopsis. Expressed in yeast, PXG4 encodes a calcium‐dependent membrane‐associated hemoprotein able to catalyze typical peroxygenase reactions. Moreover, we show here that purified recombinant PXG4 is an efficient fatty acid epoxygenase, catalyzing the oxidation of cis double bonds of unsaturated fatty acids. Physiological linoleic and linolenic acids proved to be the preferred substrates for PXG4; they are oxidized into the different positional isomers of the monoepoxides and into diepoxides. An important regioselectivity was observed; the C‐12,13 double bond of these unsaturated fatty acids being the least favored unsaturation epoxidized by PXG4, linolenic acid preferentially yielded the 9,10‐15,16‐diepoxide. Remarkably, PXG4 catalyzes exclusively the formation of (R),(S)‐epoxide enantiomers, which is the absolute stereochemistry of the epoxides found in planta. These findings pave the way for the study of the functional role of EFAs and caleosins in plants.