(S)-7'-hydroxyabscisic acid | 91897-25-5

• 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: (S)-7'-hydroxyabscisic acid
• 英文别名: 7'-hydroxy-abscisic acid；7'-hydroxyabscisic acid；nigelic acid；7'-OH-ABA；(+)-7'-hydroxyABA；7'-Hydroxy ABA；(2Z,4E)-5-[(1S)-1-hydroxy-2-(hydroxymethyl)-6,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
• CAS: 91897-25-5
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: ZGHRCSAIMSBFLK-IQSISOBESA-N

物化性质

• 沸点：
  522.4±50.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

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：

  (S)-7'-hydroxyabscisic acid 在 manganese(IV) oxide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以61%的产率得到(2Z,4E)-5-[(1S)-2-formyl-1-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic 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 (S)-7'-hydroxyabscisic 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

• Synthesis, Biological Activity, and Metabolism of 8′,8′,8′-Trideuteroabscisic Acid
  作者：Yasushi Todoroki、Sei-ichi Nakano、Nobuhiro Hirai、Toshiaki Mitsui、Hajime Ohigashi

  DOI：10.1271/bbb.61.1872

  日期：1997.1

  An 8′,8′,8′-trideuterated analog of abscisic acid (ABA) was diastereoselectively synthesized as a new analog of ABA that is resistant to 8′-hydroxyIation, the first metabolic reaction of ABA, owing to the primary kinetic isotope effect. (+)-8′,8′,8′-Trideutero-ABA showed long-term activity in the rice elongation assay. The rate of metabolism of this analog in rice cell suspension culture was about two fold slower than that of (+)-ABA. The concentration of 8′,8′-dideuterophaseic acid produced was about 1/3 that of phaseic acid converted from (+)-ABA. This result indicated that the long-lasting activity of the (+)-trideutero-ABA in the rice assay was the result of the delayed 8′-hydroxylation as expected.

  非对映选择性合成了脱落酸 (ABA) 的 8',8',8'-三氘代类似物，作为一种新的 ABA 类似物，由于初级动力学同位素效应，该类似物能够抵抗 ABA 的第一个代谢反应 8'-羟基化。 (+)-8',8',8'-Trideutero-ABA 在水稻伸长试验中显示出长期活性。该类似物在水稻细胞悬浮培养物中的代谢速率比 (+)-ABA 慢约两倍。产生的8',8'-二氘相酸的浓度约为(+)-ABA转化的菜豆酸浓度的1/3。这一结果表明，(+)-trideutero-ABA 在水稻测定中的持久活性正如预期的那样是延迟 8'-羟基化的结果。
• US8969249B2
  申请人：——

  公开号：US8969249B2

  公开（公告）日：2015-03-03
• 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.