(9Z,12Z,14E)-16-hydroxy-9,12,14-octadecatrienoic acid | 81325-65-7

• 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: (9Z,12Z,14E)-16-hydroxy-9,12,14-octadecatrienoic acid
• 英文别名: (9Z,12Z,14E)-16-hydroxyoctadeca-9,12,14-trienoic acid；16-hydroxy-9Z,12Z,14E-octadecatrienoic acid；16-Hydroxy linolenic acid；(16-HOTE)
• CAS: 81325-65-7
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: ILSZLGCGBGSHFR-CGLYFWTESA-N

物化性质

• 沸点：
  435.7±33.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

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：

  (9Z,12Z,14E)-16-hydroxy-9,12,14-octadecatrienoic acid 生成 Benzoic acid (2E,4Z,7Z)-1-ethyl-15-methoxycarbonyl-pentadeca-2,4,7-trienyl ester
  参考文献：
  名称：

  Stereoselective synthesis of hydroxy octadecatrienoic acids. The self defensive substances in rice plant

  摘要：

  DOI：

  10.1016/s0040-4039(00)84508-6
• 作为产物：
  描述：

  hepta-4,6-diyn-3-ol 在 Lindlar's catalyst 喹啉 、 lithium aluminium tetrahydride 、 氢气 、 乙基氯化镁 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 生成 (9Z,12Z,14E)-16-hydroxy-9,12,14-octadecatrienoic acid
  参考文献：
  名称：

  Stereoselective synthesis of hydroxy octadecatrienoic acids. The self defensive substances in rice plant

  摘要：

  DOI：

  10.1016/s0040-4039(00)84508-6

文献信息

• UNSATURATED HYDROXY FATTY ACIDS, THE SELF DEFENSIVE SUBSTANCES IN RICE PLANT AGAINST RICE BLAST DISEASE
  作者：Tadahiro Kato、Yoshihiro Yamaguchi、Takumi Hirano、Toshiro Yokoyama、Tadao Uyehara、Tsuneo Namai、Susumu Yamanaka、Nobuyuki Harada

  DOI：10.1246/cl.1984.409

  日期：1984.3.5

  In addition to the previously described epoxy fatty acids, five hydroxy fatty acids were characterized as self defensive substances produced in the rice plant against rice blast disease.

  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。
• 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
• Stereoselective synthesis of unsaturated C-18 hydroxy fatty acids the self defensive substances
  作者：A.V.Rama Rao、E.Rajarathnam Reddy、A.V. Purandare、Ch.V.N.S. Varaprasad

  DOI：10.1016/s0040-4020(01)90314-x

  日期：1987.1
• 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.
• RAO, A. V. RAMA;REDDY, E. RAJARATHNAM;PURANDARE, A. V.;VARAPRASAD, CH. V.+, TETRAHEDRON, 43,(1987) N 19, 4385-4394
  作者：RAO, A. V. RAMA、REDDY, E. RAJARATHNAM、PURANDARE, A. V.、VARAPRASAD, CH. V.+

  DOI：——

  日期：——