(-)-3'α-fluorophaseic acid | 164854-69-7

• 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: (-)-3'α-fluorophaseic acid
• 英文别名: (2Z,4E)-5-[(1R,4S,5S,8S)-4-fluoro-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid
• CAS: 164854-69-7
• 化学式: C₁₅H₁₉FO₅
• 分子量: 298.311
• InChiKey: SJFJBQYIHREQKA-DAFYRZLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (-)-3'α-fluorophaseic acid 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 methyl 3'α-fluorophaseate
  参考文献：
  名称：

  （S）-（+）-3'-氟脱落酸的合成，生物活性和代谢

  摘要：

  合成（S）-（+）-3'-氟脱落酸（5a）作为脱落酸的类似物，其由于在C-2'处电子密度增加而可抵抗8'-羟基脱落酸代谢成环酸的代谢环化。5a对莴苣种子萌发的抑制活性略高于脱落酸，与水稻幼苗伸长过程中的脱落酸几乎相等。当将5a施用到豆芽上时，3'-氟-8'-羟基脱落酸（8a），3'α-和3'β-氟代磷酸（9a和10a）以及3'α-和3'β-氟代二氢磷酸（11a和12a）被鉴定为游离代谢产物。甲酯8b，9b和10b以7：6：1的比例平衡存在。该结果表明，随着9a和10a的反向异构化的发生，8a是稳定的。

  DOI：

  10.1016/0040-4020(95)00340-e
• 作为产物：
  描述：

  (+)-3'-fluoroabscisic acid 在 rice cells culture 、 溶剂黄146 、 柠檬酸 作用下， 以 phosphate buffer 为溶剂， 反应 504000.0h， 生成 (-)-3'α-fluorophaseic acid
  参考文献：
  名称：

  Analysis of Isomerization Process of 8′-Hydroxyabscisic Acid and its 3′-Fluorinated Analog in Aqueous Solutions

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(00)00068-5

文献信息

• Synthesis and biological activity of 3′-chloro, -bromo, and -iodoabscisic acids, and biological activity of 3′-fluoro-8′-hydroxyabscisic acid
  作者：Sho Arai、Yasushi Todoroki、Satomi Ibaraki、Yoshikazu Naoe、Nobuhiro Hirai、Hajime Ohigashi

  DOI：10.1016/s0031-9422(99)00444-6

  日期：1999.12

  (+)-3'-Chloro, -bromo and -iodoabscisic acids were synthesized, and their biological activities and metabolism were examined, as well as that of (+)-3'-fluoroabscisic acid. This was in order to estimate the effects of altered electron density at the C-2' position of abscisic acid on both biological activity and metabolic stability. The biological activities of (+)-3'-chloro acid bromoabscisic acids were similar to, or higher than, those of(+)-abscisic acid in four bioassays, while (+)-3'-iodoabscisic acid was more potent in two bioassays and less potent than (+)-abscisic acid in the other two bioassays. The biological activities of 3'-haloabscisic acids seem to be dependent on the 3'-halogens, but not on the electron density at C-2'. The metabolism of(+)3'-haloabscisic acids to ca. 50% of their original levels in the media of rice cell suspension culture was similar to that of(+)abscisic acid. Metabolites from (+)-3'-chloro, -bromo and -iodoabscisic acids were not found in the culture media and cells, while (+)-3'-fluoroabscisic acid gave (+)-3'-fluoro-8'-hydroxyabscisic acid as a stable metabolite. (+)-3'-fluoro-8'- hydroxyabscisic acid showed biological activities lower than (+)-3'-fluoroabscisic acid, but higher than (-)-3'alpha-Fluorophascsic acid. These findings suggested that the biological activity of (+)-8'-hydroxyabscisic acid is intermediate between those of (+)abscisic acid and (-)-phaseic acid. Abscisic acid may be inactivated in a stepwise manner by metabolism in plants. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (+)-3'-氯、-溴和-碘脱落酸被合成，并对其生物学活性和代谢进行了研究，同时也研究了(+)-3'-氟脱落酸的这些性质。这是为了评估脱落酸分子中C-2'位置电子密度变化对其生物学活性和代谢稳定性的影响。在四种生物测定中，(+)-3'-氯、-溴脱落酸的生物活性与(+)-脱落酸相当，或高于后者；而(+)-3'-碘脱落酸在两种生物测定中表现出更强的活性，在另外两种测定中则活性较低。3'-卤代脱落酸的生物活性似乎取决于3'位的卤素，而不是C-2'位的电子密度。在水稻细胞悬浮培养液中，(+)-3'-卤代脱落酸的代谢程度（约降至原浓度的50%）与(+)-脱落酸相似。来自(+)-3'-氯、-溴和-碘脱落酸的代谢产物未在培养液和细胞中检出，而(+)-3'-氟脱落酸产生(+)-3'-氟-8'-羟基脱落酸作为一种稳定的代谢产物。(+)-3'-氟-8'-羟基脱落酸的生物活性低于(+)-3'-氟脱落酸，但高于(-)-3'α-氟法尼酸。这些结果表明，(+)-8'-羟基脱落酸的生物活性介于(+)-脱落酸和(-)-法尼酸之间。脱落酸可能通过植物代谢以逐步的方式被失活。© 1999 Elsevier Science Ltd. 保留所有权利。