(9S,10E,12Z,15Z)-9-羟基-10,12,15-十八碳三烯酸 | 89886-42-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (9S,10E,12Z,15Z)-9-羟基-10,12,15-十八碳三烯酸
• 中文别名: 9S-羟基-10E，12Z，15Z-十八碳三烯酸；中文名称暂缺
• 英文名称: (9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid
• 英文别名: (9S,10E,12Z,15Z)-hydroxyoctadeca-10,12,15-trienoic acid；(10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid；9(S)-hydroxy-10E,12Z,15Z-octadecatrienoic acid；9S-hydroxy-10E,12Z,15Z-octadecatrienoic acid；9-hydroxyoctadecatrienoic acid；9(S)-HOTrE；9-Hydroxy-10,12,15-octadecatrienoic acid
• CAS: 89886-42-0
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: RIGGEAZDTKMXSI-MEBVTJQTSA-N

物化性质

• 闪点：
  14 °C
• 溶解度：
  0.1 M Na2CO3：2 mg/mL； DMF：可混溶； DMSO：可混溶；乙醇：可混溶； PBS（pH 7.2）：0.8 mg/mL

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：
  0.61
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  F
• 危险类别码：
  R11
• 危险品运输编号：
  UN 1170 3
• 海关编码：
  2918199090
• 安全说明：
  S,S16,S7
• 储存条件：
  -20°C，密闭保存，干燥环境中存放

反应信息

• 作为反应物：
  描述：

  (9S,10E,12Z,15Z)-9-羟基-10,12,15-十八碳三烯酸 在 human recombinant 15-lipoxygenase type 2 、 sodium tetrahydroborate 作用下， 以 aq. buffer 为溶剂， 生成 9(S),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid
  参考文献：
  名称：

  Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA

  摘要：

  We have recently described a di-hydroxylated compound called protectin DX (PDX) which derives from docosahexaenoic acid (DHA) by double lipoxygenation. PDX exhibits anti-aggregatory and anti-inflammatory properties, that are also exhibited by similar molecules, called poxytrins, which possess the same E,Z,E conjugated triene geometry, and are synthesized from other polyunsaturated fatty acids with 22 or 20 carbons. Here we present new biological activities of di-hydroxylated metabolites deriving from alpha-linolenic acid (18:3n-3) treated by soybean 15-lipoxygenase (sLOX). We show that 18:3n-3 is converted by sLOX into mainly 13(S)-OH-18:3 after reduction of the hydroperoxide product. But surprisingly, and in contrast to DHA which is metabolized into only one di-hydroxylated compound, 18:3n-3 leads to four di-hydroxylated fatty acid isomers. We report here the complete characterization of these compounds using high field NMR and GC-MS techniques, and some of their biological activities. These compounds are: 9(R),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid, and 9(R),16(S)-dihydroxy-10E,12 Z,14E-octadecatrienoic acid. They can also be synthesized by the human recombinant 15-lipoxygenase (type 2). Their inhibitory effect on blood platelet and anti-inflammatory properties were compared with those already reported for PDX.

  DOI：

  10.1194/jlr.m035139
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 sodium tetrahydroborate 、 tomato lipoxygenase 作用下， 生成 (9S,10E,12Z,15Z)-9-羟基-10,12,15-十八碳三烯酸
  参考文献：
  名称：

  红藻藻卵石中的十八碳三烯酸的氧化：共轭四烯脂肪酸和双烯丙基羟基酸的结构和立体化学研究

  摘要：

  在制备红藻藻胆石破珊瑚的过程中酶促氧化（6 Z，9 Z，12 Z）-octadeca-6,9,12-三烯酸（γ-亚麻酸; 1a）导致形成（6 Z，8 E，10 E，12 Z）-十八烷基-6,8,10,12-丁烯酸2a和（11 R，6 Z，9 Z，12 Z）-羟基十八烯-6,9,12-三烯酸3a作为主要产品。（9 Z，12 Z，15 Z）-十八烷基-（9,12,15）-三烯酸（α-亚麻酸; 4a）以类似的方式氧化，得到（9 Z，11 E，13 E，15 Z）-octadeca-9,11， 13,15-丁烯酸（α-二十二烷酸; 5a），（11 S，9 Z，12 Z，15 Z）-羟基十八烷基9,12,15-三烯酸6a和（14 R，9 Z，12 Z，15 Z）-羟基十八烷基-9,12,15-三烯酸7a。同位素研究表明，酸1a酶转化为四烯2a伴随有立体定向消除C-8和C-11的pro - S和pro

  DOI：

  10.1039/p19930003065

文献信息

• Efficient syntheses of (10E,12Z,15Z)-9-oxo- and (9Z,11E,15E)-13-oxo-octadecatrienoic acids; two stress metabolites of wounded plants
  作者：Thomas Koch、Michal Hoskovec、Wilhelm Boland

  DOI：10.1016/s0040-4020(02)00231-4

  日期：2002.4

  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.
• METHOD OF NEUTRALISING ORGANOBORONATES WITH ACIDS
  申请人：Russel Vincent Patric

  公开号：US20100022646A1

  公开（公告）日：2010-01-28

  The use of specified compounds for the manufacture of a medicament for therapeutically neutralising an organoboronate drug. The specified compounds are typically hydroxy fatty acids or hydroperoxy fatty acids, for example 9(S)-HODE, 8(S)-HETRE or 8(S)-HEPE, or their salts or prodrugs. The organoboronate drug may be TRI 50c or a salt or prodrug thereof. Also disclosed are intravenous formulations containing the specified compounds.
• [EN] NEUTRALISING AGENTS FOR BORONIC ACID DRUGS<br/>[FR] AGENTS NEUTRALISANTS POUR MÉDICAMENTS DE TYPE ACIDES BORONIQUES
  申请人：TRIGEN LTD

  公开号：WO2006059083A1

  公开（公告）日：2006-06-08

  [EN] The use of specified compounds for the manufacture of a medicament for therapeutically neutralising an organoboronate drug. The specified compounds are typically hydroxy fatty acids or hydroperoxy fatty acids, for example 9(S)-HODE, 8(S)-HETRE or 8(S)-HEPE, or their salts or prodrugs. The organoboronate drug may be TRI 50c or a salt or prodrug thereof. Also disclosed are intravenous formulations containing the specified compounds.
  [FR] La présente invention décrit l'emploi de composés précis pour la fabrication d'un médicament employé dans la neutralisation thérapeutique d'un médicament de type organoboronate. Les composés spécifiés sont typiquement des acides gras hydroxylés ou des acides gras hydroperoxydes, par exemple 9(S)-HODE, 8(S)-HETRE ou 8(S)-HEPE, leurs sels ou leurs prodrogues. Le médicament de type organoboronate peut être le TRI 50c ou un sel ou une prodrogue de cette substance. La présente invention décrit également des formules pour administration intraveineuse contenant lesdits composés.
• Oxidation of octadecatrienoic acids in the red alga Lithothamnion corallioides: structural and stereochemical studies of conjugated tetraene fatty acids and bis allylic hydroxy acids
  作者：Mats Hamberg

  DOI：10.1039/p19930003065

  日期：——

  15-tetraenoic acid (α-parinaric acid; 5a), (11S,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid 6a, and (14R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid 7a. Isotope studies demonstrated that enzymatic conversion of the acid 1a into the tetraene 2a was accompanied by stereospecific eliminations of the pro-S and pro-R hydrogens from C-8 and C-11, respectively. The bis allylic hydroxy acid 3a was formed

  在制备红藻藻胆石破珊瑚的过程中酶促氧化（6 Z，9 Z，12 Z）-octadeca-6,9,12-三烯酸（γ-亚麻酸; 1a）导致形成（6 Z，8 E，10 E，12 Z）-十八烷基-6,8,10,12-丁烯酸2a和（11 R，6 Z，9 Z，12 Z）-羟基十八烯-6,9,12-三烯酸3a作为主要产品。（9 Z，12 Z，15 Z）-十八烷基-（9,12,15）-三烯酸（α-亚麻酸; 4a）以类似的方式氧化，得到（9 Z，11 E，13 E，15 Z）-octadeca-9,11， 13,15-丁烯酸（α-二十二烷酸; 5a），（11 S，9 Z，12 Z，15 Z）-羟基十八烷基9,12,15-三烯酸6a和（14 R，9 Z，12 Z，15 Z）-羟基十八烷基-9,12,15-三烯酸7a。同位素研究表明，酸1a酶转化为四烯2a伴随有立体定向消除C-8和C-11的pro - S和pro
• Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA
  作者：Miao Liu、Ping Chen、Evelyne Véricel、Moreno Lelli、Laetitia Béguin、Michel Lagarde、Michel Guichardant

  DOI：10.1194/jlr.m035139

  日期：2013.8

  We have recently described a di-hydroxylated compound called protectin DX (PDX) which derives from docosahexaenoic acid (DHA) by double lipoxygenation. PDX exhibits anti-aggregatory and anti-inflammatory properties, that are also exhibited by similar molecules, called poxytrins, which possess the same E,Z,E conjugated triene geometry, and are synthesized from other polyunsaturated fatty acids with 22 or 20 carbons. Here we present new biological activities of di-hydroxylated metabolites deriving from alpha-linolenic acid (18:3n-3) treated by soybean 15-lipoxygenase (sLOX). We show that 18:3n-3 is converted by sLOX into mainly 13(S)-OH-18:3 after reduction of the hydroperoxide product. But surprisingly, and in contrast to DHA which is metabolized into only one di-hydroxylated compound, 18:3n-3 leads to four di-hydroxylated fatty acid isomers. We report here the complete characterization of these compounds using high field NMR and GC-MS techniques, and some of their biological activities. These compounds are: 9(R),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid, and 9(R),16(S)-dihydroxy-10E,12 Z,14E-octadecatrienoic acid. They can also be synthesized by the human recombinant 15-lipoxygenase (type 2). Their inhibitory effect on blood platelet and anti-inflammatory properties were compared with those already reported for PDX.