(4Z,7Z,9E,11S,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid | 1607814-40-3

• 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: (4Z,7Z,9E,11S,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid
• CAS: 1607814-40-3
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: IZAUWHSXRHVGIM-PWBQNDCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (4Z,7Z,9E,11S,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三甲基硅烷化重氮甲烷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Oxylipins from the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana and their activity as TNF-α inhibitors

  摘要：

  The chemical study of the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana has led to the isolation of oxylipins. The samples of C debaryana have yielded the compounds (4Z,7Z,9E,11S,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid (1), (4Z,7E,9E,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid (2), (4Z,6E,10Z,13Z)-8-hydroxyhexadeca-4,6,10,13-tetraenoic acid (3), (4Z,8E,10Z,13Z)-7-hydroxyhexadeca-4,8,10,13-tetraenoic acid (4), and (5E,7Z,10Z,13Z)-4-hydroxyhexadeca-5,7,10,13-tetraenoic acid (5), which are derived from the fatty acid 16:4 Delta(4,7,10,13) together with the compound (5Z,9Z,11E,15Z)-13-hydroxyoctadeca-5,9,11,15-tetraenoic acid (7) derived from coniferonic acid (18:4 Delta(5,9,12,15)). In addition, the known polyunsaturated hydroxy acids 11-HHT (6), (5Z,9Z,11E)-13-hydroxyoctadeca-5,9,11-trienoic acid (8), (13S)-HOTE (9), (9E,11E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid (10), 9-HOTE (11), 12-HOTE (12), 16-HOTE (13) and (13S)-HODE (14) have also been obtained. The chemical study of N. gaditana has led to the isolation of the hydroxy acid (15S)-HEPE (15) derived from EPA (20:5 Delta(5,8,11,14,17)). The structures of the isolated compounds were established by spectroscopic means. The optical activity displayed by oxylipins 1, 2, 6, 7, 9, 10, 14, and 15 suggests the occurrence of LOX-mediated pathways in C debaryana and N. gaditana. In anti-inflammatory assays, all the tested compounds inhibited the TNF-alpha production in LPS-stimulated THP-1 macrophages. The most active oxylipin was the C-16 hydroxy acid 1, which at 25 mu M caused a 60% decrease of the TNF-alpha level. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.03.011

文献信息

• Oxylipins from the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana and their activity as TNF-α inhibitors
  作者：Carolina de los Reyes、Javier Ávila-Román、María J. Ortega、Adelina de la Jara、Sofía García-Mauriño、Virginia Motilva、Eva Zubía

  DOI：10.1016/j.phytochem.2014.03.011

  日期：2014.6

  The chemical study of the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana has led to the isolation of oxylipins. The samples of C debaryana have yielded the compounds (4Z,7Z,9E,11S,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid (1), (4Z,7E,9E,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid (2), (4Z,6E,10Z,13Z)-8-hydroxyhexadeca-4,6,10,13-tetraenoic acid (3), (4Z,8E,10Z,13Z)-7-hydroxyhexadeca-4,8,10,13-tetraenoic acid (4), and (5E,7Z,10Z,13Z)-4-hydroxyhexadeca-5,7,10,13-tetraenoic acid (5), which are derived from the fatty acid 16:4 Delta(4,7,10,13) together with the compound (5Z,9Z,11E,15Z)-13-hydroxyoctadeca-5,9,11,15-tetraenoic acid (7) derived from coniferonic acid (18:4 Delta(5,9,12,15)). In addition, the known polyunsaturated hydroxy acids 11-HHT (6), (5Z,9Z,11E)-13-hydroxyoctadeca-5,9,11-trienoic acid (8), (13S)-HOTE (9), (9E,11E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid (10), 9-HOTE (11), 12-HOTE (12), 16-HOTE (13) and (13S)-HODE (14) have also been obtained. The chemical study of N. gaditana has led to the isolation of the hydroxy acid (15S)-HEPE (15) derived from EPA (20:5 Delta(5,8,11,14,17)). The structures of the isolated compounds were established by spectroscopic means. The optical activity displayed by oxylipins 1, 2, 6, 7, 9, 10, 14, and 15 suggests the occurrence of LOX-mediated pathways in C debaryana and N. gaditana. In anti-inflammatory assays, all the tested compounds inhibited the TNF-alpha production in LPS-stimulated THP-1 macrophages. The most active oxylipin was the C-16 hydroxy acid 1, which at 25 mu M caused a 60% decrease of the TNF-alpha level. (C) 2014 Elsevier Ltd. All rights reserved.