(+/-)-abscisic acid cis-1',4'-diol | 20110-02-5

• 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: (+/-)-abscisic acid cis-1',4'-diol
• 英文别名: ω-<1'r.4'c-Dihydroxy-2'.6'.6'-trimethyl-cyclohexen-(2')-yl>-3-methyl-pentadien-(2.4)-saeure
• CAS: 20110-02-5；34781-49-2；34781-50-5；84026-26-6；85718-96-3；97806-70-7；109785-51-5；113349-71-6
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: MWGXQVSTMXPXIW-PMCPXRDQSA-N

物化性质

• 熔点：
  183-184 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  454.0±45.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.76
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-abscisic acid cis-1',4'-diol 在 caesium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  几种脱落酸乙酰糖酯及其衍生物的制备与分析

  摘要：

  外消旋脱落酸 (ABA)，通过还原 4' 酮衍生自 ABA 的顺式和反式 1', 4'-二醇 (ABA diols)，以及相应的 4'-O-乙酸酯通过反应转化为各种乙酰糖酯它们的铯盐与源自葡萄糖、半乳糖、乳糖和麦芽糖的 1-氯乙酰糖。开发了在反相柱上使用高效液相色谱 (LC) 进行乙酰糖酯的分析分离。获得了各种乙酰糖酯的连续流动二次离子质谱 (CFSIMS)，并使用采用多反应监测的 LC/CFSIMS 协议来检测从用 ABA 处理的植物细胞获得的乙酰化提取物中的 ABA 乙酰葡萄糖酯。关键词：脱落酸，乙酰糖酯，合成，色谱，质谱。

  DOI：

  10.1139/v96-027
• 作为产物：
  描述：

  (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以3.7 mg的产率得到(2Z,4E)-5-(1',4'-dihydroxy-2',6',6'-trimethyl-4'-oxo-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienoic acid
  参考文献：
  名称：

  Biosynthesis of Abscisic Acid by the Non-mevalonate Pathway in Plants, and by the Mevalonate Pathway in Fungi

  摘要：

  通过向郁金香幼枝的插条和两种产生ABA的植物病原真菌饲喂[1-13C]-D-葡萄糖，对生物合成ABA的途径进行了研究。分离的ABA样品的13C-NMR光谱显示，郁金香树中ABA的1、5、6、4′、7′和9′碳被标记为13C，而真菌中ABA的2、4、6、1′、3′、5′、7′、8′和9′碳被标记为13C。前者对应异戊烯基焦磷酸的C-1和-5，后者对应异戊烯基焦磷酸的C-2、-4和-5。这一发现揭示了ABA在植物中通过非甲基戊二酸途径生物合成，而在真菌中通过甲基戊二酸途径生物合成。郁金香树中13C标记的β-胡萝卜素表明，标记碳的位置与ABA相同，与通过类胡萝卜素生物合成ABA一致。郁金香树的脂类醇类也通过非甲基戊二酸途径生物合成。

  DOI：

  10.1271/bbb.64.1448

文献信息

• Biosynthesis of Abscisic Acid by the Non-mevalonate Pathway in Plants, and by the Mevalonate Pathway in Fungi
  作者：Nobuhiro HIRAI、Ryuji YOSHIDA、Yasushi TODOROKI、Hajime OHIGASHI

  DOI：10.1271/bbb.64.1448

  日期：2000.1

  The biosynthetic pathways to abscisic acid (ABA) were investigated by feeding [1-13C]-D-glucose to cuttings from young tulip tree shoots and to two ABA-producing phytopathogenic fungi. 13C-NMR spectra of the ABA samples isolated showed that the carbons at 1, 5, 6, 4′, 7′ and 9′ of ABA from the tulip tree were labeled with 13C, while the carbons at 2, 4, 6, 1′, 3′, 5′, 7′, 8′ and 9′ of ABA from the fungi were labeled with 13C. The former corresponds to C-1 and -5 of isopentenyl pyrophosphate, and the latter to C-2, -4 and -5 of isopentenyl pyrophosphate. This finding reveals that ABA was biosynthesized by the non-mevalonate pathway in the plant, and by the mevalonate pathway in the fungi. 13C-Labeled β-carotene from the tulip tree showed that the positions of the labeled carbons were the same as those of ABA, being consistent with the biosynthesis of ABA via carotenoids. Lipiferolide of the tulip tree was also biosynthesized by the non-mevalonate pathway.

  通过向郁金香幼枝的插条和两种产生ABA的植物病原真菌饲喂[1-13C]-D-葡萄糖，对生物合成ABA的途径进行了研究。分离的ABA样品的13C-NMR光谱显示，郁金香树中ABA的1、5、6、4′、7′和9′碳被标记为13C，而真菌中ABA的2、4、6、1′、3′、5′、7′、8′和9′碳被标记为13C。前者对应异戊烯基焦磷酸的C-1和-5，后者对应异戊烯基焦磷酸的C-2、-4和-5。这一发现揭示了ABA在植物中通过非甲基戊二酸途径生物合成，而在真菌中通过甲基戊二酸途径生物合成。郁金香树中13C标记的β-胡萝卜素表明，标记碳的位置与ABA相同，与通过类胡萝卜素生物合成ABA一致。郁金香树的脂类醇类也通过非甲基戊二酸途径生物合成。
• Synthesis, structural characterization and effect on human granulocyte intracellular cAMP levels of abscisic acid analogs
  作者：Marta Bellotti、Annalisa Salis、Alessia Grozio、Gianluca Damonte、Tiziana Vigliarolo、Andrea Galatini、Elena Zocchi、Umberto Benatti、Enrico Millo

  DOI：10.1016/j.bmc.2014.11.035

  日期：2015.1

  The phytohormone abscisic acid (ABA), in addition to regulating physiological functions in plants, is also produced and released by several mammalian cell types, including human granulocytes, where it stimulates innate immune functions via an increase of the intracellular cAMP concentration ([cAMP]i).We synthesized several ABA analogs and evaluated the structure-activity relationship, by the systematical modification of selected regions of these analogs. The resulting molecules were tested for their ability to inhibit the ABA-induced increase of [cAMP]i in human granulocytes. The analogs with modified configurations at C-2' and C-3' abrogated the ABA-induced increase of the [cAMP]i and also inhibited several pro-inflammatory effects induced by exogenous ABA on granulocytes and monocytes. Accordingly, these analogs could be suitable as novel putative anti-inflammatory compounds. (C) 2014 Elsevier Ltd. All rights reserved.
• Preparation and analysis of some acetosugar esters of abscisic acid and derivatives
  作者：J. Balsevich、G. Bishop、S.L. Jacques、L.R. Hogge、D.J.H. Olson、N. Laganière

  DOI：10.1139/v96-027

  日期：1996.2.1

  Continuous flow secondary ion mass spectra (CFSIMS) of the various acetosugar esters were obtained and an LC/CFSIMS protocol employing multiple reaction monitoring was used to detect ABA acetoglucose ester in an acetylated extract obtained from plant cells that had been treated with ABA. Key words: abscisic acid, acetosugar esters, synthesis, chromatography, mass spectrometry.

  外消旋脱落酸 (ABA)，通过还原 4' 酮衍生自 ABA 的顺式和反式 1', 4'-二醇 (ABA diols)，以及相应的 4'-O-乙酸酯通过反应转化为各种乙酰糖酯它们的铯盐与源自葡萄糖、半乳糖、乳糖和麦芽糖的 1-氯乙酰糖。开发了在反相柱上使用高效液相色谱 (LC) 进行乙酰糖酯的分析分离。获得了各种乙酰糖酯的连续流动二次离子质谱 (CFSIMS)，并使用采用多反应监测的 LC/CFSIMS 协议来检测从用 ABA 处理的植物细胞获得的乙酰化提取物中的 ABA 乙酰葡萄糖酯。关键词：脱落酸，乙酰糖酯，合成，色谱，质谱。