(5Z,8Z,11Z,14Z,16E)-18(R)-triisopropylsilyloxyeicosapentaenoic acid methyl ester | 1310569-68-6

• 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,14Z,16E)-18(R)-triisopropylsilyloxyeicosapentaenoic acid methyl ester
• 英文别名: methyl (5Z,8Z,11Z,14Z,16E,18R)-18-tri(propan-2-yl)silyloxyicosa-5,8,11,14,16-pentaenoate
• CAS: 1310569-68-6
• 化学式: C₃₀H₅₂O₃Si
• 分子量: 488.827
• InChiKey: GIIPFXHPTGVJOO-QVBHCIJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.25
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5Z,8Z,11Z,14Z,16E)-18(R)-triisopropylsilyloxyeicosapentaenoic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 methyl (R,5Z,8Z,11Z,14Z,16E)-18-hydroxyicosa-5,8,11,14,16-pentaenoate
  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：

  1-(三甲基硅烷基)-1-戊炔-3-酮 在 哌啶 、 咪唑 、 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 水 、 三正丁基氢锡 、 potassium carbonate 、 异丙醇 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 62.0h， 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

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.