9-hydro(pero)xy-10E,12Z,15Z-octadecatrienoic acid | 64265-94-7

• 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: 9-hydro(pero)xy-10E,12Z,15Z-octadecatrienoic acid
• 英文别名: (10E,12Z,15Z)-9-hydroperoxyoctadeca-10,12,15-trienoic acid
• CAS: 64265-94-7
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: RWKJTIHNYSIIHW-CUHSZNQNSA-N

物化性质

• 沸点：
  466.1±45.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  9-hydro(pero)xy-10E,12Z,15Z-octadecatrienoic acid 在 Fusarium oxysporum-9S-dioxygenases-allene oxide synthase 作用下， 生成 8-[3-[(2Z,5Z)-octa-2,5-dienylidene]oxiran-2-yl]octanoic acid
  参考文献：
  名称：

  Polyunsaturated C18 fatty acids derivatized with Gly and Ile as an additional tool for studies of the catalytic evolution of fungal 8- and 9-dioxygenases

  摘要：

  The fungal linoleate diol synthase (LDS) family contains over twenty characterized 8-, 9-, and 10-dioxygenases (DOX), usually fused to catalytically competent cytochromes P450. Crystal structures are not available, but indirect evidence suggests that linoleic acid enters the active site of 8R-DOX-LDS headfirst and enters 9S-DOX-allene oxide synthase (AOS) with the omega-end (tail) first. Fatty acids derivatized with amino acids can conceivably be used to study oxidation in tail first position by enzymes, which bind natural fatty acids headfirst. The results might reveal catalytic similarities of homologous enzymes. 8R-DOX-5,8-LDS oxidize 18:2n-6-Ile and 18:2n-6-Gly in tail first position to 9S-hydroperoxy metabolites, albeit with less position and stereo specificity than 9S-DOX-AOS. The oxygenation mechanism of 9S-DOX-AOS with antarafacial hydrogen abstraction at C-11 and oxygen insertion at C-9 was also retained. Two homologues, 8R-DOX-7,8-LDS and 8R-DOX-AOS, oxidized 18:2n-6-Ile and 18:2n-6-Gly at C-9, suggesting a conserved feature of 8R-DOX domains. 9R-DOX-AOS, with 54% sequence identity to 9S-DOX-AOS, did not oxidize the derivatized C-18 fatty acids. 9Z,12Z-16:2, two carbon shorter than 18:n-6 from the omega-end, was rapidly metabolized to an alpha-ketol, but 7Z,10Z-16:2 was not a substrate. An unsaturated carbon chain from C-1 to C-8 was apparently more important than the configuration at the omega-end. 8R-DOX-LDS and 9R-DOX-AOS may thus bind 18:2n-6 in the same orientation. The oxidation of 18:2n-6 in straight or reverse head-to-tail positions illustrates evolutionary traits between 8- and 9-DOX domains. Fatty acids derivatized with amino acids provide a complementary tool for the analysis of evolution of enzymes.

  DOI：

  10.1016/j.bbalip.2018.08.012
• 作为产物：
  描述：

  Octadeca-9,12,15-trienoate 在 Fusarium oxysporum-9S-dioxygenases-allene oxide synthase 、 氧气 作用下， 生成 9-hydro(pero)xy-10E,12Z,15Z-octadecatrienoic acid
  参考文献：
  名称：

  Polyunsaturated C18 fatty acids derivatized with Gly and Ile as an additional tool for studies of the catalytic evolution of fungal 8- and 9-dioxygenases

  摘要：

  The fungal linoleate diol synthase (LDS) family contains over twenty characterized 8-, 9-, and 10-dioxygenases (DOX), usually fused to catalytically competent cytochromes P450. Crystal structures are not available, but indirect evidence suggests that linoleic acid enters the active site of 8R-DOX-LDS headfirst and enters 9S-DOX-allene oxide synthase (AOS) with the omega-end (tail) first. Fatty acids derivatized with amino acids can conceivably be used to study oxidation in tail first position by enzymes, which bind natural fatty acids headfirst. The results might reveal catalytic similarities of homologous enzymes. 8R-DOX-5,8-LDS oxidize 18:2n-6-Ile and 18:2n-6-Gly in tail first position to 9S-hydroperoxy metabolites, albeit with less position and stereo specificity than 9S-DOX-AOS. The oxygenation mechanism of 9S-DOX-AOS with antarafacial hydrogen abstraction at C-11 and oxygen insertion at C-9 was also retained. Two homologues, 8R-DOX-7,8-LDS and 8R-DOX-AOS, oxidized 18:2n-6-Ile and 18:2n-6-Gly at C-9, suggesting a conserved feature of 8R-DOX domains. 9R-DOX-AOS, with 54% sequence identity to 9S-DOX-AOS, did not oxidize the derivatized C-18 fatty acids. 9Z,12Z-16:2, two carbon shorter than 18:n-6 from the omega-end, was rapidly metabolized to an alpha-ketol, but 7Z,10Z-16:2 was not a substrate. An unsaturated carbon chain from C-1 to C-8 was apparently more important than the configuration at the omega-end. 8R-DOX-LDS and 9R-DOX-AOS may thus bind 18:2n-6 in the same orientation. The oxidation of 18:2n-6 in straight or reverse head-to-tail positions illustrates evolutionary traits between 8- and 9-DOX domains. Fatty acids derivatized with amino acids provide a complementary tool for the analysis of evolution of enzymes.

  DOI：

  10.1016/j.bbalip.2018.08.012

文献信息

• Replacement of two amino acids of 9 R -dioxygenase-allene oxide synthase of Aspergillus niger inverts the chirality of the hydroperoxide and the allene oxide
  作者：Linda Sooman、Anneli Wennman、Mats Hamberg、Inga Hoffmann、Ernst H. Oliw

  DOI：10.1016/j.bbalip.2015.11.009

  日期：2016.2

  amino acids for the stereospecificity. Recombinant EHA25900 oxidized 18:2n-6 sequentially to 9R-hydroperoxy-10(E),12(Z)-octadecadienoic acid (9R-HPODE) and to a 9R(10)-allene oxide. 9S- and 9R-DOX-AOS catalyze abstraction of the pro-R hydrogen at C-11, but the direction of oxygen insertion differs. A comparison between twelve 9-DOX domains of 9S- and 9R-DOX-AOS revealed conserved amino acid differences

  黑曲霉的基因组编码一个融合蛋白（EHA25900），该序列可以与尖孢镰刀菌的9S-双加氧酶（DOX）-氧化烯合酶（AOS），镰刀菌和炭疽菌复合物的同系物和与曲霉菌的同源物具有超过62％的序列同一性，包括曲霉菌的（DOX）-9R-AOS。目的是表征EHA25900的酶促活性，并鉴定立体特异性的关键氨基酸。重组EHA25900依次将18：2n-6氧化为9R-氢过氧-10（E），12（Z）-十八碳二烯酸（9R-HPODE）和9R（10）-丙二烯氧化物。9S-和9R-DOX-AOS催化C-11上pro-R氢的提取，但是氧的插入方向不同。比较9S-和9R-DOX-AOS的12个9-DOX域，可以发现保守的氨基酸差异，这可能有助于产品的手性。9R-DOX-AOS（黑曲霉）的Gly616Ile替代增加了9S-HPODE和9S（10）-丙二烯氧化物的生物合成，而Phe627Leu替代导致9S-HPODE和
• 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.
• MUSKMELON (CUCUMIS MELO) HYDROPEROXIDE LYASE AND USES THEREOF
  申请人：Firmenich S.A.

  公开号：EP1268819B1

  公开（公告）日：2006-06-07
• Inducing Agent for Plant Root
  申请人：Yokoyama Mineyuki

  公开号：US20070293400A1

  公开（公告）日：2007-12-20

  An inducing agent for plant root including a ketol unsaturated fatty acid having 5 to 24 carbon atoms, 1 to 6 double bonds between carbon atoms and an α ketol structure or γ ketol structure (in particular 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid is preferable), which inducing agent for plant root may be used to promote or induce the root growth even when transplanting by cutting plants for which root generation is hard such as pine, cedar, tea, chestnut, may be used even for root growth of cuttings of Prunus×yedoensis (cherry trees) for which root growth is considered impossible, Hypericum chinense for which is transplantation by cutting is said to be difficult, and Paraserianthes falcataria Becker useful as a material for plywood, and may be used by a simple technique such as spraying.
• Plant activator
  申请人：Yokoyama Mineyuki

  公开号：US20080234133A1

  公开（公告）日：2008-09-25

  An object of the present invention is to determine novel means of activating plants; more particularly, means of controlling plant growth, such as means of promoting growth, means of controlling dormancy, means of imparting tolerance against stress for plants (dryness, high or low temperatures, osmotic pressure, etc.), and means of preventing aging. The present inventors have found that the above object can be achieved by providing plant activators containing, as an active ingredient, C 4 -C 24 ketol fatty acids, in particular, 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid.