8'-hydroxyabscisic acid

• 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: 8'-hydroxyabscisic acid
• 英文别名: 8'-hydroxy-ABA；(+)-8'-Hydroxyabscisic acid；(2Z,4E)-5-[(1R,6R)-1-hydroxy-6-(hydroxymethyl)-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: AVFORCKFTWHFAR-ZSIFGTMLSA-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：

  8'-hydroxyabscisic acid 生成 (2Z,4E)-3-甲基-5-[(1S)-1beta-羟基-2,6-二甲基-6beta,2beta-(环氧甲桥)-4-氧代环己烷-1-基]-2,4-戊二烯酸
  参考文献：
  名称：

  Deuterium-labeled Phaseic Acid and Dihydrophaseic Acids for Internal Standards

  摘要：

  植物体内脱落酸的浓度不仅受生物合成的调节，也受新陈代谢的调节。脱落酸通过 8′-羟基脱落酸代谢为相思酸，相思酸再转化为双氢相思酸及其表聚物。对这些代谢物以及脱落酸进行定量分析对于了解植物体内脱落酸浓度的变化非常重要。然而，目前还没有适合定量分析的代谢物内标物的报道。我们利用脱落酸与 8′-羟基脱落酸的平衡反应制备了 7′-氘标记的脱落酸，其氘含量为 86%。通过还原 7′-氘标记的相酸，可获得 7′-氘标记的二氢相酸。以氚标记的代谢物为内标，测定植物器官中代谢物的含量。

  DOI：

  10.1271/bbb.67.2408
• 作为产物：
  描述：

  (+)-脱落酸 在 还原型辅酶II(NADPH)四钠盐 作用下， 反应 0.17h， 生成 8'-hydroxyabscisic acid
  参考文献：
  名称：

  Enlarged analogues of uniconazole, new azole containing inhibitors of ABA 8′-hydroxylase CYP707A

  摘要：

  We enlarged the uniconazole (UNI) molecule to find a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, and synthesized various UNI derivatives that were substituted with hydrophilic and hydrophobic groups at the 4-chlorine of the phenyl group of UNI using click chemistry. Considering its potency in ABA 8'-hydroxylase inhibition, its small effect on seedling growth, and its ease of application, UT4, the UNI derivative containing the C-4 alkyltriazole, was the best candidate for a highly selective inhibitor of ABA 8'-hydroxylase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.137

文献信息

• EFFICIENT SCALABLE SYNTHESES OF ABSCISIC ACID, 8'-ACETYLENE ABSCISIC ACID AND 8'-CYCLOPROPYL ABSCISIC ACID
  申请人：NATIONAL RESEARCH COUNCIL OF CANADA

  公开号：US20170057899A1

  公开（公告）日：2017-03-02

  Methods are provided for synthesis of abscisic acid and 8′ analogues thereof (including an enantiopure 8′-acetylene analogue) including methods wherein the previously reported first step of oxidation of 2,6-dimethylphenol (VI) to 2,6-dimethylbenzoquinone, mono ketal (VII) is replaced by a novel two step process comprising (i) oxidation of 2,6-dimethylphenol (VI) using potassium peroxymonosulfate with a catalytic amount of iodobenzene to produce 2,6-dimethylbenzoquinone (XVI) and (ii) ketalization of 2,6-dimethylbenzoquinone (XVI) using ethylene glycol, trimethylorthoformate with a catalytic amount of p-toluenesulfonic acid to produce 2,6-dimethylbenzoquinone, mono ketal (VII).

  提供了合成脱落酸及其8′类似物的方法（包括对映纯的8′-乙炔类似物），其中包括先前报道的将2,6-二甲基苯酚（VI）氧化为2,6-二甲基苯醌单缩酮（VII）的第一步氧化步骤被一种新颖的两步过程取代的方法，该两步过程包括（i）使用过氧单硫酸钾和少量碘苯氧化2,6-二甲基苯酚（VI）以产生2,6-二甲基苯醌（XVI），以及（ii）使用乙二醇、三甲基正甲酸酯和少量对甲苯磺酸催化剂缩酮化2,6-二甲基苯醌（XVI）以产生2,6-二甲基苯醌单缩酮（VII）。
• Analysis of Isomerization Process of 8′-Hydroxyabscisic Acid and its 3′-Fluorinated Analog in Aqueous Solutions
  作者：Yasushi Todoroki、Nobuhiro Hirai、Hajime Ohigashi

  DOI：10.1016/s0040-4020(00)00068-5

  日期：2000.3

  8'-Hydroxyabscisic acid (8'-HOABA), the first metabolite of abscisic acid (ABA) in plants, is spontaneously isomerized to low bioactive phaseic acid (PA). We investigated thermodynamic and kinetic properties of the isomerization process in aqueous solution buffered at the various pHs, along with the effects of 3'-fluorine. The 8'-HOABA/PA ratio at equilibrium was 2:98 at 25 degrees C, while the 3'-fluoro-8 'HOABA/3 'alpha-fluoro-PA ratio was 16:84, indicating that introduction of a fluorine at C-3' thermodynamically reduced isomerization of 8-'HOABA to PA. The isomerization became more rapid as pH increased; the rate constant at pH 10 was higher than that at pH 3 by a factor of 2000, Introduction of a fluorine at C-3' reduced the reaction rate by raising the activation enthalpy. This indicated mat 8'-HOABA was also kinetically stabilized by the 3'-fluorine. These findings suggested that the control of pH and modification of the enone moiety of the ring would be useful to manipulate the catabolic inactivation rate of ABA. (C) 2000 Elsevier Science Ltd. All rights reserved.
• US9725392B2
  申请人：——

  公开号：US9725392B2

  公开（公告）日：2017-08-08
• Enlarged analogues of uniconazole, new azole containing inhibitors of ABA 8′-hydroxylase CYP707A
  作者：Yasushi Todoroki、Hikaru Aoyama、Saori Hiramatsu、Minaho Shirakura、Hataitip Nimitkeatkai、Satoru Kondo、Kotomi Ueno、Masaharu Mizutani、Nobuhiro Hirai

  DOI：10.1016/j.bmcl.2009.07.137

  日期：2009.10

  We enlarged the uniconazole (UNI) molecule to find a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, and synthesized various UNI derivatives that were substituted with hydrophilic and hydrophobic groups at the 4-chlorine of the phenyl group of UNI using click chemistry. Considering its potency in ABA 8'-hydroxylase inhibition, its small effect on seedling growth, and its ease of application, UT4, the UNI derivative containing the C-4 alkyltriazole, was the best candidate for a highly selective inhibitor of ABA 8'-hydroxylase. (C) 2009 Elsevier Ltd. All rights reserved.
• Deuterium-labeled Phaseic Acid and Dihydrophaseic Acids for Internal Standards
  作者：Nobuhiro HIRAI、Satoru KONDO、Hajime OHIGASHI

  DOI：10.1271/bbb.67.2408

  日期：2003.1

  The concentration of abscisic acid in plants is regulated not only by biosynthesis, but also by metabolism. Abscisic acid is metabolized to phaseic acid via 8′-hydroxyabscisic acid, and phaseic acid is then converted to dihydrophaseic acid and its epimer. A quantitative analysis of these metabolites is important as well as that of abscisic acid to understand changes in the concentration of abscisic acid in plants. However, no internal standards of the metabolites suitable for quantitative analysis have been reported. We prepared 7′-deuterium-labeled phaseic acid with a deuterium content of 86%, using the equilibrium reaction between phaseic acid and 8′-hydroxyabscisic acid. 7′-Deuterium-labeled dihydrophaseic acids were obtained by reducing 7′-deuterium-labeled phaseic acid. The levels of the metabolites in plant organs were determined by using the deuterated metabolites as internal standards.

  植物体内脱落酸的浓度不仅受生物合成的调节，也受新陈代谢的调节。脱落酸通过 8′-羟基脱落酸代谢为相思酸，相思酸再转化为双氢相思酸及其表聚物。对这些代谢物以及脱落酸进行定量分析对于了解植物体内脱落酸浓度的变化非常重要。然而，目前还没有适合定量分析的代谢物内标物的报道。我们利用脱落酸与 8′-羟基脱落酸的平衡反应制备了 7′-氘标记的脱落酸，其氘含量为 86%。通过还原 7′-氘标记的相酸，可获得 7′-氘标记的二氢相酸。以氚标记的代谢物为内标，测定植物器官中代谢物的含量。