(Z)-8-Hydroxy-oct-6-enoic acid methyl ester | 83606-27-3

• 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: (Z)-8-Hydroxy-oct-6-enoic acid methyl ester
• CAS: 83606-27-3；125198-14-3
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: WXKVJWCFYRXPCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  12.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-8-Hydroxy-oct-6-enoic acid methyl ester 在 manganese(IV) oxide 、 正丁基锂 、 敌草腈 、 碘 作用下， 反应 32.0h， 生成 methyl (6E,8Z,11Z)-6,8,11-eicosatrienoate
  参考文献：
  名称：

  Design, synthesis, and 5-lipoxygenase-inhibiting properties of 1-thio-substituted butadienes

  摘要：

  The synthesis of novel 1-thio-substituted butadienes, designed as mechanism-based 5-lipoxygenase inhibitors, is described. The structure of these compounds closely resembles a proposed high-energy intermediate during the lipoxygenation of arachidonic acid. They demonstrate 5-lipoxygenase inhibition in vitro and in vivo. The most potent compound is 15a with an IC50 of 1.8 microM in vitro. LTC4 release was inhibited by 80% after intraperitoneal administration of 15c at a dose of 2 mg/kg.

  DOI：

  10.1021/jm00166a013
• 作为产物：
  描述：

  methyl 8-hydroxy-6-octynoate 在 镍 氢气 作用下， 以91%的产率得到(Z)-8-Hydroxy-oct-6-enoic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and 5-lipoxygenase-inhibiting properties of 1-thio-substituted butadienes

  摘要：

  The synthesis of novel 1-thio-substituted butadienes, designed as mechanism-based 5-lipoxygenase inhibitors, is described. The structure of these compounds closely resembles a proposed high-energy intermediate during the lipoxygenation of arachidonic acid. They demonstrate 5-lipoxygenase inhibition in vitro and in vivo. The most potent compound is 15a with an IC50 of 1.8 microM in vitro. LTC4 release was inhibited by 80% after intraperitoneal administration of 15c at a dose of 2 mg/kg.

  DOI：

  10.1021/jm00166a013