(13R,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid | 10219-69-9

• 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: (13R,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid
• 英文别名: (9Z,11E,13R)-13-hydroxyoctadeca-9,11-dienoic acid；13(R)-hydroxy-9Z,11E-octadecadienoic acid；(13R)-hydroxylinoleic acid；coriolic acid；13-HODE；(R)-coriolic acid
• CAS: 10219-69-9
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: HNICUWMFWZBIFP-PIHGWCCBSA-N

物化性质

• 沸点：
  422.7±20.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50 mg/ml； DMSO：50 mg/ml；乙醇：50 mg/ml； PBS pH 7.2：1 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 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：

  (13R,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid 在 三乙基硅烷 、 4-二甲氨基吡啶 、 Co(tdcpp) 、 氧气 、 乙酸酐 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 (R)-(E)-10-oxo-11-octadecen-13-olide
  参考文献：
  名称：

  10-oxo-11（E）-octadecen-13-olide和相关脂肪酸的对映选择性合成

  摘要：

  由亚油酸合成了10-oxo-11（E）-octadecen-13-olide（1）的S和R对映异构体的第一步且很短，它是玉米的细胞毒脂肪酸衍生物seco-acid 2。通过脂氧合酶催化的不对称氧合和卟啉钴催化的还原氧合，将酸（3）作为关键步骤反应。

  DOI：

  10.1016/s0040-4039(97)01359-2
• 作为产物：
  描述：

  methyl 2-deoxy-3,5-di-O-p-toluenesulfonyl-D-erythro-pentofuranoside 在 copper(l) iodide 、 正丁基锂 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 15.5h， 生成 (13R,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid
  参考文献：
  名称：

  A concise synthesis of (R)-hydroxy-E,Z-diene fatty acids: preparation of 12(R)-hete, tetranor-12(R)-hete, and 13(R)-hode

  摘要：

  Chiral E-enals derived from functionalized 2-deoxy-D-ribofuranoses by ylide-induced beta-elimination were exploited for the synthesis of fatty acid metabolites containing the (R)-hydroxy-E,Z-diene subunit.

  DOI：

  10.1016/s0040-4039(00)79912-6

文献信息

• Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus
  作者：Stefan Schulz、Selma Yildizhan、Katja Stritzke、Catalina Estrada、Lawrence E. Gilbert

  DOI：10.1039/b710284d

  日期：——

  The four major components present in scent gland extracts of the male Costa Rica longwing butterflies Heliconius cydno and Heliconius pachinus were identified as 12- and 14-membered macrolides containing a C18-carbon skeleton. By use of micro-reactions and spectrometric examinations, structural proposals were made and subsequently proven by synthesis, using ring-closing-metathesis as the key steps. These macrolides, (9Z,11E,13S)-octadeca-9,11-dien-13-olide (5, S-coriolide), (9Z,11E,13S,15Z)-octadeca-9,11,15-trien-13-olide (6), (9Z,13S)-octadec-9-en-13-olide (13), and (9Z,11S)-octadec-9-en-11-olide (25), are biosynthetically obviously derived from oleic, linoleic, and linolenic acids. Their absolute configurations were determined by gas chromatographic investigations on chiral phases, showing all to possess (S)-configuration.

  哥斯达黎加长翼蝴蝶（Heliconius cydno 和 Heliconius pachinus）雄性蜕皮腺萃取物中发现的四种主要成分被确定为含有C18碳骨架的12-和14-membered大环内酯。通过微反应和光谱检测，提出了结构方案，并通过合成验证，这一过程以环闭合重排为关键步骤。这些大环内酯包括（9Z,11E,13S）-十八烯-9,11-二烯-13-内酯（5, S-柯里内酯）、（9Z,11E,13S,15Z）-十八烯-9,11,15-三烯-13-内酯（6）、（9Z,13S）-十八烯-9-烯-13-内酯（13）和（9Z,11S）-十八烯-9-烯-11-内酯（25），这些化合物在生物合成上显然源自油酸、亚油酸和亚麻酸。它们的绝对构型通过对手性相的气相色谱分析确定，显示全部为(S)-构型。
• Synthesis of both enantiomers of the docosahexaenoic acid ester of 13-hydroxyoctadecadienoic acid (13-DHAHLA)
  作者：Anders Vik、Trond Vidar Hansen、Ondrej Kuda

  DOI：10.1016/j.tetlet.2019.151331

  日期：2019.12

  Due to their minute presence in human samples, access to synthetic material of each enantiomer becomes necessary for exact structural elucidation and extensive biological evaluation. Herein we report the multi-milligram synthesis of both enantiomers of the docosahexaenoic acid ester of 13-hydroxyoctadecadienoic acid (13-DHAHLA) from commercially available starting materials.

  最近，已经报道了几种不同类别的内源脂质，它们显示出抗糖尿病和抗炎作用。由于它们在人体样品中的存在极少，因此对于精确的结构阐明和广泛的生物学评估，必须获得每种对映异构体的合成材料。在本文中，我们报道了从市售的起始原料的十三-羟基十八碳二烯酸二十二碳六烯酸酯（13-DHAHLA）的两种对映异构体的多毫克合成。
• Synthesis and physiological activities of both enantiomers of coriolic acid and their geometric isomers
  作者：Yuichi Kobayashi、Sentaro Okamoto、Toshiyuki Shimazaki、Yoshinori Ochiai、Fumie Sato

  DOI：10.1016/s0040-4039(00)96431-1

  日期：1987.1

  Both enantiomers of coriolic acid and their geometric isomers are synthesized highly selectively. These acids are found to exhibit similar inhibition activity toward spore germination of rice blast fungus.

  皮质酸的对映异构体及其几何异构体都是高度选择性合成的。发现这些酸对稻瘟病菌的孢子萌发表现出相似的抑制活性。
• Biotransformation of C20- and C22-polyunsaturated fatty acids and fish oil hydrolyzates to <i>R</i>,<i>R</i>-dihydroxy fatty acids as lipid mediators using double-oxygenating 15<i>R</i>-lipoxygenase
  作者：Jin Lee、Yoon-Joo Ko、Jin-Byung Park、Deok-Kun Oh

  DOI：10.1039/d4gc00308j

  日期：——

  C20- and C22-dihydroxy fatty acids (DiHFAs) are bioactive lipid mediators (LMs) in humans.

  C20- 和 C22-二羟基脂肪酸（DiHFAs）是人体中具有生物活性的脂质介质（LMs）。
• 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.