(9Z,11E,15Z)-13-oxooctadeca-9,11,15-trienoic acid

• 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: (9Z,11E,15Z)-13-oxooctadeca-9,11,15-trienoic acid
• 英文别名: 13-oxo-9Z,11E,15Z-octadecatrienoic acid；(9Z,11E,15Z)-13-oxooctadecatrienoic acid；13-keto-9Z,11E,15Z-octadecatrienoic acid
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: BNMYUQILBYIYOG-JDTPQGGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (9Z,11E,13S,15Z)-13-羟基-9,11,15-十八碳三烯酸 在 silica gel 、 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以58%的产率得到(9Z,11E,15Z)-13-oxooctadeca-9,11,15-trienoic acid
  参考文献：
  名称：

  Efficient syntheses of (10E,12Z,15Z)-9-oxo- and (9Z,11E,15E)-13-oxo-octadecatrienoic acids; two stress metabolites of wounded plants

  摘要：

  Configurationally pure 9-oxo-10E, 12Z,15Z- and 13-oxo-9Z,11E,15E-octadecatrienoic acid are available from linolenic acid via regioselective functionalisation using lipoxygenases from soybean or tomato at specific pH conditions. Reduction of the resulting hydro-peroxides followed by oxidation of the resulting allylic alcohols with Bobbin's reagent yields the configurationally pure but labile ketotrienoic acids 4 and 5 without concomitant isomerisation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00231-4

文献信息

• Oxidation of C18 Hydroxy-Polyunsaturated Fatty Acids to Epoxide or Ketone by Catalase-Related Hemoproteins Activated with Iodosylbenzene
  作者：Tarvi Teder、William E. Boeglin、Alan R. Brash

  DOI：10.1007/s11745-017-4271-0

  日期：2017.7

  and 9,10‐epoxy‐13‐keto derivatives; equivalent transformations occurred with 9S‐hydroxy‐linoleic acid as substrate. In parallel incubations in the presence of iodosylbenzene, human catalase displayed no activity towards 13S‐hydroxy‐linoleic acid, as expected from the highly restricted access to its active site. The results indicated that with suitable transformation to Compound I, monooxygenase activity

  当使用碘基苯激活时，检查了与过氧化氢酶相关的小型过氧化氢酶相关的血蛋白，它们可以与脂肪酸氢过氧化物反应，以检测其潜在的单加氧酶活性。测试的蛋白为镰刀镰刀菌41 kD过氧化氢酶血红蛋白（Fg-cat，基因FGSG_02217），荧光假单胞菌Pfl01过氧化氢酶（37.5 kD，保藏号WP_011333788.1）和鸟分枝杆菌ssp。副结核病33 kD过氧化氢酶（基因MAP-2744c）。选择13-羟基-十八碳烯酸（通常不反应）作为底物，因为这些酶会与相应的13 S-氢过氧化物特异性反应（Pakhomova等人18：2559-2568，5; Teder等人。1862：706–715，14）。在亚碘酰苯FG-猫的存在下转化13 š羟基脂肪酸两种产品：13 15,16-双键š羟基α亚麻酸被立体特异性地氧化为15小号，16 - [R -顺-epoxide或13-羟基被氧化为13-酮。通过UV，HPL
• Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways
  作者：Aldwin Anterola、Cornelia Göbel、Ellen Hornung、George Sellhorn、Ivo Feussner、Howard Grimes

  DOI：10.1016/j.phytochem.2008.11.012

  日期：2009.1

  Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 alpha-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering plants. To identify the fatty acid substrates used by moss lipoxygenases, eight lipoxygenase genes from Physcomitrella patens were heterologously expressed in Escherichia coli, and then analyzed for lipoxygenase activity using linoleic, alpha-linolenic and arachidonic acids as substrates. Among the eight moss lipoxygenases, only seven were found to be enzymatically active in vitro, two of which selectively used arachidonic acid as the substrate, while the other five preferred alpha-linolenic acid. Based on enzyme assays using a Clark-type oxygen electrode, all of the active lipoxygenases had an optimum pH at 7.0, except for one with highest activity at pH 5.0. HPLC analyses indicated that the two arachidonic acid lipoxygenases form (12S)-hydroperoxy eicosatetraenoic acid as the main product, while the other five lipoxygenases produce mainly (13S)-hydroperoxy octadecatrienoic acid from alpha-linolenic acid. These results suggest that mosses may have both C20 and C18 based oxylipin pathways. Published by Elsevier Ltd.
• Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols
  作者：Gilles Iacazio

  DOI：10.1016/s0009-3084(03)00087-2

  日期：2003.10

  Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these keto compounds to yield back the starting alcohols, but now as racemic mixtures, was also conducted using CeCl3-NaBH4, once again without noticeable modification of the stereochemistry of the double bonds. These reactions proved the usefulness of the chemoenzymatic access to oxylipins through the use of lipoxygenases with various regiospecificity, combined with chemical transformations of the formed hydro(pero)xides. (C) 2003 Elsevier Ireland Ltd. All rights reserved.