(9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid methyl ester | 10075-07-7

• 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: (9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid methyl ester
• 英文别名: (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid methyl ester；9(S)-hydroxylinoleic acid methyl ester；methyl (9S)-hydroxyoctadeca-(10E,12Z)-dienoate；methyl (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoate
• CAS: 10075-07-7
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: WRXGTVUDZZBNPN-QPHMHISKSA-N

物化性质

• 沸点：
  414.5±33.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  (9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid methyl ester 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 sodium borotritide 作用下， 以 甲醇 、 正戊烷 为溶剂， 反应 48.08h， 生成 methyl (+/-)-9-hydroxy<9-3H>octadeca-(10E,12Z)-dienoate
  参考文献：
  名称：

  Crombie, Leslie; Holloway, Stephen J., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2425 - 2434

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 盐酸 、 phosphate buffer 、 tomato lipoxygenase 、 tin(ll) chloride 、 Tween 20 作用下， 以 甲醇 、 乙醚 、 氯仿 、 乙酸乙酯 为溶剂， 反应 8.17h， 生成 (9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid methyl ester
  参考文献：
  名称：

  9-Hydroxy-10,12-octadecadienoic acid (9-HODE) and 13-hydroxy-9,11-octadecadienoic acid (13-HODE): excellent markers for lipid peroxidation

  摘要：

  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.

  DOI：

  10.1016/s0009-3084(97)00070-4

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。
• Isolation and Identification of Antifungal Fatty Acids from the Basidiomycete <i>Gomphus floccosus</i>
  作者：Charles L. Cantrell、Bethany P. Case、E. Edward Mena、Toby M. Kniffin、Stephen O. Duke、David E. Wedge

  DOI：10.1021/jf8008662

  日期：2008.7.1

  the basidiomycete Gomphus floccosus (Schw.) Singer indicated the presence of fungitoxic compounds in the ethyl acetate fraction against the plant pathogens Colletotrichum fragariae, Colletotrichum gloeosporioides, and Colletotrichum acutatum. Bioassay-guided fractionation of this fraction resulted in the isolation of the bioactive fatty acids (9 S,10 E,12 Z)-9-hydroxy-10,12-octadecadienoic acid (1)

  担子菌Gomphus floccosus（Schw。）子实体的提取物的生物自显影研究表明，乙酸乙酯级分中存在真菌毒性化合物，可抵抗植物病原体草莓，炭疽菌和番茄。该部分的生物测定指导分馏导致生物活性脂肪酸（9 S，10 E，12 Z）-9-羟基-10,12-十八碳二烯酸（1），（9 E，11 Z）-13的分离-氧代-9,11-十八碳二烯酸（2）和（10 E，12 E）-9-氧代-10,12-十八碳二烯酸（3）。在体外剂量反应研究中，进一步评估了这三种脂环素对更大范围的真菌植物病原体（草莓角梭菌，球孢梭菌，角形梭菌，灰葡萄孢，尖孢镰刀菌，暗纹枯萎菌和小菜蛾）的活性。番茄属物种是对这些化合物最敏感的真菌。在治疗120小时后，暗黑假单胞菌的化合物1、2和3的IC50值分别为1.0、4.5和23 microM，而captan阳性对照的IC50值为1.1 microM。
• Preparation of the enantiomers of hydroxy-C18 fatty acids and their anti-rice blast fungus activities
  作者：Tadahiro Kato、Toshio Nakai、Rumiko Ishikawa、Aya Karasawa、Tsuneo Namai

  DOI：10.1016/s0957-4166(01)00486-4

  日期：2001.10

  the infected rice plants as an enantiomeric mixture with <10% e.e., a procedure for the chemical preparation of both enantiomers was explored, starting from the original fatty acids 4 and 5. The anti-rice blast fungus activities of both enantiomers of the allylic alcohols 1–3 and epoxy α-linolenic acids 12 and 13 demonstrate no noticeable correlation between the activity and chirality.

  为了检查抗稻瘟病菌的活性和烯丙基醇的手性之间的相关性1 - 3，这是从受感染的水稻植物，其特征为具有<10％ee的，对于两者的化学制备过程对映体混合物从原始脂肪酸4和5开始探索对映体。烯丙基醇的两种对映体的抗稻瘟病菌的活动13和环氧树脂α-亚麻酸12和13表现出的活性和手性之间没有明显的相关性。
• Properties of a mini 9R-lipoxygenase from Nostoc sp. PCC 7120 and its mutant forms
  作者：Alexandra-Zoi Andreou、Marian Vanko、Lydia Bezakova、Ivo Feussner

  DOI：10.1016/j.phytochem.2008.03.002

  日期：2008.6

  linoleic acid esterified to a bulky phosphatidylcholine molecule as a substrate suggested a tail-fist binding orientation of the substrate. Site directed mutagenesis of the alanine to glycine did not cause alterations in the stereospecificity of the products, while mutation of the alanine to valine or isoleucine modified both regio- and enantioselectivity of the enzyme. Kinetic measurements revealed

  脂氧合酶 (LOX) 由一类催化多不饱和脂肪酸的区域和立体定向双加氧的酶组成。目前的报道提出，R-脂肪氧化酶活性位点的保守甘氨酸残基和S-脂肪氧化酶相应位置的丙氨酸残基在决定产物的立体化学方面起着至关重要的作用。最近，来自 Nostoc sp. 的具有亚油酸二醇合酶活性的双功能脂肪氧化酶。鉴定了具有 R 立体特异性的 PCC7120 和迄今为止在手性特异性序列决定簇位置携带丙氨酸而不是保守甘氨酸的独特特征。在大肠杆菌中表达后纯化重组羧基末端结构域。该酶使用酯化为庞大的磷脂酰胆碱分子的亚油酸作为底物的能力表明底物的尾拳结合方向。将丙氨酸定点诱变为甘氨酸不会引起产物立体特异性的改变，而将丙氨酸突变为缬氨酸或异亮氨酸改变了酶的区域选择性和对映选择性。动力学测量表明，用 Gly 或 Val 取代 Ala 不会显着影响反应特性，而 A162I 突变体显示 vmax 降低。根据获得的诱变数据，
• Chemo-enzymatic synthesis of methyl 9(S)-HODE (dimorphecolic acid methyl ester) and methyl 9(S)-HOTE catalysed by barley seed lipoxygenase
  作者：Dominique Martini、Gérard Buono、Jean-Luc Montillet、Gilles Iacazio

  DOI：10.1016/0957-4166(96)00167-x

  日期：1996.5

  The straightforward chemo-enzymatic synthesis of methyl 9(S)-HODE (dimorphecolic acid methyl ester) and methyl 9(S)-HOTE, from linoleic and alpha-linolenic acids, using barley seeds lipoxygenase under oxygen pressure and at high substrate concentration, is described. Copyright (C) 1996 Elsevier Science Ltd