(5Z,8Z,11Z)-pentadeca-5,8,11-trien-14-ynoic acid methyl ester | 1310569-63-1

• 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: (5Z,8Z,11Z)-pentadeca-5,8,11-trien-14-ynoic acid methyl ester
• 英文别名: methyl (5Z,8Z,11Z)-pentadeca-5,8,11-trien-14-ynoate
• CAS: 1310569-63-1
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: PNVHOSOYWVFBKE-AGRJPVHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5Z,8Z,11Z)-pentadeca-5,8,11-trien-14-ynoic acid methyl ester 在 哌啶 、 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 水 、 锌 作用下， 以 苯 为溶剂， 反应 20.0h， 生成 (5Z,8Z,11Z,14Z,16E)-18(R)-triisopropylsilyloxyeicosapentaenoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis and Bioactivity of 18(R)-Hydroxyeicosapentaenoic Acid

  摘要：

  Resolvins are family of lipid mediators derived from omega-3 polyunsaturated fatty acids, which are generated during the resolution phase of acute inflammation. Resolvin E1 is biosynthesized from eicosapentaenoic add via 18(R)-hydroxyeicosapentaenoic acid (18R-HEPE) in the Cox-2 and lipoxygenase mediated pathway and has proven to exhibit potent anti-inflammatory activity. We report herein the first total chemical synthesis of 18R-HEPE and demonstrate that this compound displays in vivo bioactivity by blocking neutrophil infiltration in a murine model of zymosan-induced peritonitis.

  DOI：

  10.1021/jo2002243
• 作为产物：
  描述：

  5-己炔酸甲酯 在 sodium tetrahydroborate 、 copper(l) iodide 、 四溴化碳 、 氢气 、 nickel(II) acetate tetrahydrate 、 potassium carbonate 、 乙二胺 、 三苯基膦 、 cesium fluoride 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (5Z,8Z,11Z)-pentadeca-5,8,11-trien-14-ynoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis and Bioactivity of 18(R)-Hydroxyeicosapentaenoic Acid

  摘要：

  Resolvins are family of lipid mediators derived from omega-3 polyunsaturated fatty acids, which are generated during the resolution phase of acute inflammation. Resolvin E1 is biosynthesized from eicosapentaenoic add via 18(R)-hydroxyeicosapentaenoic acid (18R-HEPE) in the Cox-2 and lipoxygenase mediated pathway and has proven to exhibit potent anti-inflammatory activity. We report herein the first total chemical synthesis of 18R-HEPE and demonstrate that this compound displays in vivo bioactivity by blocking neutrophil infiltration in a murine model of zymosan-induced peritonitis.

  DOI：

  10.1021/jo2002243

文献信息

• Total Synthesis and Bioactivity of 18(<i>R</i>)-Hydroxyeicosapentaenoic Acid
  作者：Venkata R. Krishnamurthy、Ann Dougherty、Carolyn A. Haller、Elliot L. Chaikof

  DOI：10.1021/jo2002243

  日期：2011.7.1

  Resolvins are family of lipid mediators derived from omega-3 polyunsaturated fatty acids, which are generated during the resolution phase of acute inflammation. Resolvin E1 is biosynthesized from eicosapentaenoic add via 18(R)-hydroxyeicosapentaenoic acid (18R-HEPE) in the Cox-2 and lipoxygenase mediated pathway and has proven to exhibit potent anti-inflammatory activity. We report herein the first total chemical synthesis of 18R-HEPE and demonstrate that this compound displays in vivo bioactivity by blocking neutrophil infiltration in a murine model of zymosan-induced peritonitis.