methyl (4E)-5-(2-(acetoxymethyl)-1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate | 951171-19-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (4E)-5-(2-(acetoxymethyl)-1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate
• CAS: 951171-19-0
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: IUJYTBDFJWWMPD-PSSAGTMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.9
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (4E)-5-(2-(acetoxymethyl)-1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate 在 porcine liver esterase 、 potassium phosphate buffer 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 0.08h， 生成 (+/-) 7'-hydroxyabscisic acid methyl ester
  参考文献：
  名称：

  Effect of the minor ABA metabolite 7′-hydroxy-ABA on Arabidopsis ABA 8′-hydroxylase CYP707A3

  摘要：

  To examine the effect of the minor abscisic acid (ABA) metabolite 7'-hydroxy-ABA on Arabidopsis ABA W-hydroxylase (CYP707A3), we developed a novel and facile, four-step synthesis of 7'-hydroxy-ABA from alpha-ionone. Structural analogues of Thydroxy-ABA, 1'-deoxy-7'-hydroxy-ABA, and 7'-oxo-ABA were also synthesized to evaluate the role of the T-hydroxyl group on binding to the enzyme. The result of enzyme inhibition assay suggests that the local polarity at C-T, neither steric bulkiness nor overall molecular hydrophilicity, would be the major reason why (+)-7'-hydroxy-ABA is not a potent inhibitor of CYP707A3. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.018
• 作为产物：
  描述：

  alpha-ionone 在 chromium(VI) oxide 、 碘 、 乙酸酐 、 双(三甲基硅烷基)氨基钾 、 叔丁醇 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 23.5h， 生成 methyl (4E)-5-(2-(acetoxymethyl)-1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate
  参考文献：
  名称：

  Effect of the minor ABA metabolite 7′-hydroxy-ABA on Arabidopsis ABA 8′-hydroxylase CYP707A3

  摘要：

  To examine the effect of the minor abscisic acid (ABA) metabolite 7'-hydroxy-ABA on Arabidopsis ABA W-hydroxylase (CYP707A3), we developed a novel and facile, four-step synthesis of 7'-hydroxy-ABA from alpha-ionone. Structural analogues of Thydroxy-ABA, 1'-deoxy-7'-hydroxy-ABA, and 7'-oxo-ABA were also synthesized to evaluate the role of the T-hydroxyl group on binding to the enzyme. The result of enzyme inhibition assay suggests that the local polarity at C-T, neither steric bulkiness nor overall molecular hydrophilicity, would be the major reason why (+)-7'-hydroxy-ABA is not a potent inhibitor of CYP707A3. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.018