8,15-dihydroxyeicosa-5Z,9E,11Z,13E-tetraenoic acid | 221393-78-8

• 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: 8,15-dihydroxyeicosa-5Z,9E,11Z,13E-tetraenoic acid
• 英文别名: 8,15-dihydroxy-5Z,9E,11Z,13E-eicosatetraenoic acid；8,15-DiHETE；(5Z,9E,11Z,13E)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid
• CAS: 221393-78-8
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: NNPWRKSGORGTIM-RCDCWWQHSA-N

物化性质

• 沸点：
  510.8±50.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  花生四烯酸 在 soybean 15-lipoxygenase 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 5,15-diHETE 、 8,15-dihydroxyeicosa-5Z,9E,11Z,13E-tetraenoic acid
  参考文献：
  名称：

  Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase

  摘要：

  Resolvins and protectins are important anti-inflammatory and pro-resolution compounds derived from the enzymatic oxidation of omega-3 fatty acids all-cis-5,8,11,14,17-eicosapentaenoic acid (EPA) and all-cis-4,7,10,13,16,19-docosahexaenoic acid (DHA). We have developed a simple, controlled method to synthesize an array of resolvin and protectin analogs from fatty acid starting materials using soybean 15-lipoxygenase. The conditions were optimized for the production of both mono-and dihydroxy derivatives, with enzyme concentration and pH found to have a significant effect on the reaction products. The methods were applied to five biologically important omega-3 and omega-6 fatty acid substrates. Mono-and dihydroxy compounds were successfully synthesized from all substrates and the products were characterized by normal phase (NP) HPLC, GC-MS, TOF-MS, UV-visible (UV-vis) spectroscopy, and NMR spectroscopy. The methods could be further applied to any polyunsaturated fatty acids containing the cis-1,4,7,10-undecatetraene moiety to produce a range of novel compounds with potential biological activity.-Dobson, E. P., C. J. Barrow, J. A. Kralovec, and J. L. Adcock. Controlled formation of mono-and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase. J. Lipid Res. 2013. 54: 1439-1447.

  DOI：

  10.1194/jlr.m036186

文献信息

• Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase
  作者：Eleanor P. Dobson、Colin J. Barrow、Jaroslav A. Kralovec、Jacqui L. Adcock

  DOI：10.1194/jlr.m036186

  日期：2013.5

  Resolvins and protectins are important anti-inflammatory and pro-resolution compounds derived from the enzymatic oxidation of omega-3 fatty acids all-cis-5,8,11,14,17-eicosapentaenoic acid (EPA) and all-cis-4,7,10,13,16,19-docosahexaenoic acid (DHA). We have developed a simple, controlled method to synthesize an array of resolvin and protectin analogs from fatty acid starting materials using soybean 15-lipoxygenase. The conditions were optimized for the production of both mono-and dihydroxy derivatives, with enzyme concentration and pH found to have a significant effect on the reaction products. The methods were applied to five biologically important omega-3 and omega-6 fatty acid substrates. Mono-and dihydroxy compounds were successfully synthesized from all substrates and the products were characterized by normal phase (NP) HPLC, GC-MS, TOF-MS, UV-visible (UV-vis) spectroscopy, and NMR spectroscopy. The methods could be further applied to any polyunsaturated fatty acids containing the cis-1,4,7,10-undecatetraene moiety to produce a range of novel compounds with potential biological activity.-Dobson, E. P., C. J. Barrow, J. A. Kralovec, and J. L. Adcock. Controlled formation of mono-and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase. J. Lipid Res. 2013. 54: 1439-1447.