7'-hydroxy (-)-R-abscisic acid | 134676-92-9

• 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: 7'-hydroxy (-)-R-abscisic acid
• 英文别名: (-)-7'-hydroxyabscisic acid；(2Z,4E)-5-[(1R)-1-hydroxy-2-(hydroxymethyl)-6,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
• CAS: 134676-92-9
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: ZGHRCSAIMSBFLK-PMRCHOJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7'-hydroxy (-)-R-abscisic acid 在 manganese(IV) oxide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以46%的产率得到(-)-7'-oxoabscisic acid
  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：

  (E)-[5,5-dimethyl-6-(3-oxobut-1-enyl)cyclohex-1-enyl]methyl acetate 在 chromium(VI) oxide 、 porcine liver esterase 、 potassium phosphate buffer 、 乙酸酐 、 双(三甲基硅烷基)氨基钾 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 21.0h， 生成 7'-hydroxy (-)-R-abscisic acid
  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

文献信息

• 7′-hydroxy (−)-R-abscisic acid: A metabolite of feeding (−)-R-abscisic acid to Xanthium strumarium
  作者：Gregory L. Boyer、Ján A.D. Zeevaart

  DOI：10.1016/s0031-9422(00)81562-9

  日期：1986.4

  Abstract Feeding of(±)-abscisic acid to leaves of Xanthium strumarium resulted in formation of a new metabolite. The compound was identified as 7′-hydroxy (−)-R-abscisic acid by high resolution mass spectrometry of its methyl ester and monoacetate, and by optical rotary dispersion. The numbering system for abscisic acid has been extended to include the exocyclic methyl groups. Feeding racemic [2-14C]abscisic

  摘要 将(±)-脱落酸喂入苍耳草叶片导致新代谢物的形成。该化合物通过其甲酯和单乙酸酯的高分辨率质谱以及旋光色散鉴定为 7'-羟基 (-)-R-脱落酸。脱落酸的编号系统已扩展到包括环外甲基。将外消旋 [2-14C] 脱落酸喂给苍耳子叶导致大约 20% 的放射性标记化合物转化为新的代谢物。有证据表明，在 Xanthium 中，只有脱落酸的合成 (-)-R-对映异构体在 7'-位被羟基化。
• Effect of the minor ABA metabolite 7′-hydroxy-ABA on Arabidopsis ABA 8′-hydroxylase CYP707A3
  作者：Hajime Shimomura、Hideo Etoh、Masaharu Mizutani、Nobuhiro Hirai、Yasushi Todoroki

  DOI：10.1016/j.bmcl.2007.06.018

  日期：2007.9

  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.