13-hydroxy-9Z,11E,15Z-octadecatrienoic acid | 36129-21-2

• 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: 13-hydroxy-9Z,11E,15Z-octadecatrienoic acid
• 英文别名: (9Z,11E,15Z)-13-hydroxy-9,11,15-octadecatrienoic acid；13-hydroxy-cis-9,trans-11,cis-15-octadecatrienoic acid；13-HoTrE；(9Z,11E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid
• CAS: 36129-21-2
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: KLLGGGQNRTVBSU-JDTPQGGVSA-N

物化性质

• 沸点：
  431.5±30.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 13-hydroxy-9Z,11E,15Z-octadecatrienoic acid 生成 methyl 9-hydroxylinelonate
  参考文献：
  名称：

  UNSATURATED HYDROXY FATTY ACIDS, THE SELF DEFENSIVE SUBSTANCES IN RICE PLANT AGAINST RICE BLAST DISEASE

  摘要：

  除了之前描述的环氧脂肪酸外，还鉴定出五种羟基脂肪酸作为水稻植物对抗稻瘟病的自我防御物质。

  DOI：

  10.1246/cl.1984.409
• 作为产物：
  描述：

  (E)-13-hydroxytridec-9-yn-11-enoic acid 在 Lindlar's catalyst 喹啉 、 manganese(IV) oxide 、 氢气 、 magnesium 作用下， 以 乙醇 、 氯仿 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 13-hydroxy-9Z,11E,15Z-octadecatrienoic acid
  参考文献：
  名称：

  Synthesis of 13-Hydroxy-9Z,11E,15Z-octadecatrienoic Acid

  摘要：

  Stereoselective synthesis of 15,16-didehydro coriolic acid, starting from pent-2-en-4-yn-1-ol is described.

  DOI：

  10.1080/00397919408011743

文献信息

• STRUCTURE AND SYNTHESIS OF 11,12,13-TRIHYDROXY-9<i>Z</i>,15<i>Z</i>-OCTADECADIENOIC ACIDS FROM RICE PLANT SUFFERING FROM RICE BLAST DISEASE
  作者：Tadahiro Kato、Yoshihiro Yamaguchi、Shin-ichi Ohnuma、Tadao Uyehara、Tsuneo Namai、Mitsuaki Kodama、Yoshinori Shiobara

  DOI：10.1246/cl.1986.577

  日期：1986.4.5

  Structural elucidation including the absolute configuration was carried out on the trihydroxyoctadecadienoic acids isolated from rice plant suffering from rice blast disease.

  对从患有稻瘟病的水稻植物中分离的三羟基十八碳二烯酸进行了包括绝对构型在内的结构解析。
• Solubilization and properties of the enzyme-cleaving 13-l-hydroperoxylinolenic acid in tea leaves
  作者：A. Hatanaka、T. Kajiwara、J. Sekiya、S. Inouye

  DOI：10.1016/0031-9422(82)80005-8

  日期：1982.1

  The membrane bound hydroperoxide lyase (E″2) which catalyses the cleavage of 13-l-hydroperoxides (18:3-OOH and1 8:2-OOH) of linolenic and lin

  膜结合氢过氧化物裂解酶 (E″2) 催化亚麻酸和亚麻酸的 13-l-氢过氧化物 (18:3-OOH 和 1 8:2-OOH) 的裂解
• Beyond Autoxidation and Lipoxygenases: Fatty Acid Oxidation Products in Plant Oils
  作者：Elisabeth Koch、Ariane Löwen、Nadja Kampschulte、Kathrin Plitzko、Michelle Wiebel、Katharina M. Rund、Ina Willenberg、Nils Helge Schebb

  DOI：10.1021/acs.jafc.3c02724

  日期：2023.9.6

  18-OH-C18:3, three isomers of 12-OH-C18:2, and one of 15-OH-C18:2. 16-OH-C18:3 and 18-OH-C18:3 were tentatively identified as 16-OH-ALA and 18-OH-ALA, respectively, based on autoxidation and terminal hydroxylation of ALA using CYP4F2. Investigation of formation pathways suggests that fatty acid desaturase 3 is involved in the formation of the 12-OH-C18:2 isomers, 15-HODE, and its isomer. The dominantly

  几十年来，植物油中亚油酸（LA，C18：2 n6）和α-亚麻酸（ALA，C18：3 n3）氧化的研究重点是自动氧化形成和脂加氧酶衍生的9-氢（过）xy-和13-氢(过)氧基-LA和-ALA。在这里，我们使用非靶向方法表明，其他羟基脂肪酸在植物油中含量更丰富。液相色谱-质谱和气相色谱-质谱分析揭示了亚麻籽油和菜籽油中高度丰富的峰。使用可靠的参考标准，其中七个峰被确定为 9-、10-、12-、13- 和 15-HODE 以及 9- 和 13-HOTrE。此外，还根据保留时间、[M–H] −离子及其碎片离子（16-OH-C18:3、18-OH-C18:3、12 的三种异构体）对六个峰进行了表征。 -OH-C18:2，和15-OH-C18:2之一。基于使用 CYP4F2 对 ALA 进行自氧化和末端羟基化，16-OH-C18:3 和 18-OH-C18:3 分别初步鉴定为 16-OH-ALA 和
• Antimicrobial prevention and treatment of human immunedeficience virus and other infectious diseases
  申请人：——

  公开号：US20030104082A1

  公开（公告）日：2003-06-05

  An improved medical treatment and medicine is provided to quickly and safely resolve HIV and other microbial infections. The inexpensive medicine can be self administered and maintained for the prescribed time. The attractive medicine comprises an antimicrobial concentrate comprising microbe inhibitors, phytochemicals or isolates. Desirably, the effective medicine comprises a surfactant and an aqueous carrier or solvent and a nutrient. In the preferred form, the medicine comprises: Echinacea and Commiphora myrrha phytochemicals, benzalkonium chloride, a sterile water solution, and folic acid.

  提供了一种改进的医疗方法和药物，可快速、安全地解决艾滋病毒和其他微生物感染问题。这种药物价格低廉，可自行服用并在规定时间内维持。这种有吸引力的药物包括一种抗微生物浓缩物，其中含有微生物抑制剂、植物化学物质或分离物。理想情况下，有效药物包括表面活性剂和水性载体或溶剂以及营养素。在优选形式中，药物包括紫锥菊和 紫锥菊 植物化学物质、苯扎氯铵、无菌水溶液和叶酸。
• 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.