8-hydroxyoleic acid | 1071-64-3

• 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: 8-hydroxyoleic acid
• 英文别名: 8-hydroxy-9(Z)-octadecenoic acid；8-hydroxyoctadec-9Z-enoic acid；8-Hydroxyoleic acid；(Z)-8-hydroxyoctadec-9-enoic acid
• CAS: 1071-64-3
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: JEXIZLHRWZNJIX-KAMYIIQDSA-N

物化性质

• 熔点：
  37.5 °C
• 沸点：
  410.9±33.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  油酸 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 8-hydroxyoleic acid 、 11-hydroxy-9(Z)-octadecenoic acid
  参考文献：
  名称：

  嗜热栖热菌HB27的孤儿细胞色素P450 CYP175A1对单脂肪酸的氧化

  摘要：

  已经研究了CYP175A1对各种链长（C16–C24）的饱和和单不饱和脂肪酸的单加氧反应的催化活性，以评估该孤儿热稳定细胞色素P450酶的酶促性质。结果表明，该酶可以催化单不饱和脂肪酸的反应，但不能催化饱和脂肪酸的反应。使用ESI-MS和GC-MS进行的产品分析表明，取决于烯键式双键（C═C）的构型，CYP175A1催化单烯脂肪酸的单加氧反应具有重要的区域选择性。当双键处于顺式构型时，发现环氧脂肪酸是主要产物，而发现两个烯丙基-羟基脂肪酸是次要产物。但是当双键处于反式构型时，产物分布相反。发现棕榈油酸的氧化效率最高（链长为C16），但活性与链长或脂肪酸的不饱和位置没有直接关系。分子对接计算表明，单烯脂肪酸的“ U”型构型特别负责它们在酶口袋中的结合，这也与在氧化反应中观察到的区域选择性一致。目前的结果提供证据，CYP175A1可以催化几种单烯脂肪酸的区域选择性氧化反应，尽管它不能催化相应的

  DOI：

  10.1021/bi300514j

文献信息

• Linolenate 9 <i>R</i> ‐Dioxygenase and Allene Oxide Synthase Activities of <i>Lasiodiplodia theobromae</i>
  作者：Fredrik Jernerén、Felipe Eng、Mats Hamberg、Ernst H. Oliw

  DOI：10.1007/s11745-011-3622-5

  日期：2012.1

  sequential action of 13-lipoxygenase, allene oxide synthase (AOS), and allene oxide cyclase. The fungus Lasiodiplodia theobromae can produce large amounts of JA and was recently reported to form the JA precursor 12-oxophytodienoic acid. The objective of our study was to characterize the fatty acid dioxygenase activities of this fungus. Two strains of L. theobromae with low JA secretion (~0.2 mg/L medium)

  茉莉酸 (JA) 是由亚麻酸 (18:3n-3) 通过 13-脂肪氧化酶、丙二烯氧化合酶 (AOS) 和丙二烯氧化环化酶的顺序作用合成的。真菌 Lasiodiplodia theobromae 可产生大量 JA，最近据报道可形成 JA 前体 12-氧代植物二烯酸。我们研究的目的是表征这种真菌的脂肪酸双加氧酶活性。两株低 JA 分泌的 L. theobromae 菌株（~0.2 mg/L 培养基）将 18:3n-3 氧化为 5,8-二羟基-9Z,12Z,15Z-十八碳三烯酸以及 9R-氢过氧-10E,12Z， 15Z-十八碳三烯酸，通过 AOS 活性代谢为 9-羟基-10-氧代-12Z,15Z-十八碳二烯酸。用亚油酸 (18:2n-6) 观察到类似的转化。使用 [11S-(2)H]18 的研究：图 2n-6 揭示了推定的 9R-双加氧酶催化了 11R 氢的立体特异性去除，然后是 C-9 处双氧的表面攻击。来自这些
• Gene Deletion of 7,8-Linoleate Diol Synthase of the Rice Blast Fungus
  作者：Fredrik Jernerén、Ane Sesma、Marina Francheschetti、Mats Hamberg、Ernst H. Oliw

  DOI：10.1074/jbc.m109.062810

  日期：2010.2

  Linoleate diol synthases (LDS) are heme enzymes, which oxygenate 18:2n-6 sequentially to (8R)-hydroperoxylinoleic acid ((8R)-HPODE) and to(5S,8R)-dihydroxy-, (7S,8S)-dihydroxy-, or (8R,11S)-dihydroxylinoleic acids (DiHODE). The genome of the rice blast fungus, Magnaporthe oryzae, contains two genes with homology to LDS. M. oryzae oxidized 18:2n-6 to (8R)-HPODE and to (7S,8S)-DiHODE, (6S,8R)-DiHODE, and (8R,11S)-HODE. Small amounts of 10-hydroxy-(8E,12Z)-octadecadienoic acid and traces of 5,8-DiHODE were also detected by liquid chromatography-mass spectrometry. The contribution of the 7,8-LDS gene to M. oryzae pathogenicity was evaluated by replacement of the catalytic domain with hygromycin and green fluorescent protein variant (SGFP) cassettes. This genetically modified strain Delta 7,8-LDS infected rice leaves and roots and formed appressoria and conidia as the native fungus. The Delta 7,8-LDS mutant had lost the capacity to biosynthesize all the metabolites except small amounts of 8-hydroxylinoleic acid. Studies with stereospecifically deuterated linoleic acids showed that (8R)-HPODE was formed by abstraction of the pro-S hydrogen at C-8 and antarafacial oxygenation, whereas (7S,8S)-DiHODE and (8R,11S)-DiHODE were formed from (8R)-HPODE by suprafacial hydrogen abstraction and oxygenation at C-7 and C-11, respectively. A mac1 suppressor mutant (Delta mac1 sum1-99) of M. oryzae, which shows cAMP-independent protein kinase A activity, oxygenated 18:2n-6 to increased amounts of (10R)-HPODE and (5S,8R)-DiHODE. Expression of the 7,8-LDS gene but not of the second homologue was detected in the suppressor mutant. This suggests that PKA-mediated signaling pathway regulates the dioxygenase and hydroperoxide isomerase activities of M. oryzae.
• [EN] LIPID ANALYSIS<br/>[FR] ANALYSE LIPIDIQUE
  申请人：UNIV BONN

  公开号：WO2014001527A2

  公开（公告）日：2014-01-03

  The present invention relates to a method for the detection of a lipid comprising reacting an alkyne-modified lipid derivative and an azido-modified coumarin compound, purifying the resulting compound using chromatography and detecting the reaction product. In a further aspect the present invention provides new alkyne lipid derivatives, new methods of alkyne lipid synthesis, new uses of such compounds and new methods employing these compounds.
• Oxygenation of Monoenoic Fatty Acids by CYP175A1, an Orphan Cytochrome P450 from <i>Thermus thermophilus</i> HB27
  作者：Sandeep Goyal、Shibdas Banerjee、Shyamalava Mazumdar

  DOI：10.1021/bi300514j

  日期：2012.10.9

  monooxygenation of the monoenoic fatty acids depending on the ethylenic double bond (C═C) configuration. When the double bond was in cis-configuration, an epoxy fatty acid was found to be the major product and two allyl-hydroxy fatty acids were found to be the minor products. But when the double bond was in trans-configuration the product distribution was reversed. The oxygenation efficiency was found to be

  已经研究了CYP175A1对各种链长（C16–C24）的饱和和单不饱和脂肪酸的单加氧反应的催化活性，以评估该孤儿热稳定细胞色素P450酶的酶促性质。结果表明，该酶可以催化单不饱和脂肪酸的反应，但不能催化饱和脂肪酸的反应。使用ESI-MS和GC-MS进行的产品分析表明，取决于烯键式双键（C═C）的构型，CYP175A1催化单烯脂肪酸的单加氧反应具有重要的区域选择性。当双键处于顺式构型时，发现环氧脂肪酸是主要产物，而发现两个烯丙基-羟基脂肪酸是次要产物。但是当双键处于反式构型时，产物分布相反。发现棕榈油酸的氧化效率最高（链长为C16），但活性与链长或脂肪酸的不饱和位置没有直接关系。分子对接计算表明，单烯脂肪酸的“ U”型构型特别负责它们在酶口袋中的结合，这也与在氧化反应中观察到的区域选择性一致。目前的结果提供证据，CYP175A1可以催化几种单烯脂肪酸的区域选择性氧化反应，尽管它不能催化相应的