(9S,10S,12Z,15Z)-9,10-dihydroxyoctadeca-12,15-dienoic acid | 1400693-74-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (9S,10S,12Z,15Z)-9,10-dihydroxyoctadeca-12,15-dienoic acid
• CAS: 1400693-74-4
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: QRHSEDZBZMZPOA-ZQLDCXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9S,10S,12Z,15Z)-9,10-dihydroxyoctadeca-12,15-dienoic acid 在 acyl-CoA oxidase 、 2-enoylacyl-CoA hydratase 、 3-hydroxyacyl-CoA dehydrogenase 、 3-ketoacyl-CoA thiolase 、 acyl-CoA synthetase 作用下， 反应 12.0h， 生成 (5S,6S,8Z,11Z)-5,6-dihydroxytetradeca-8,11-dienoic acid 、 (7S,8S,10Z,13Z)-7,8-dihydroxyhexadeca-10,13-dienoic acid
  参考文献：
  名称：

  Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet

  摘要：

  Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity toward Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the alpha-ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereochemistry at the oxymethine carbon was determined based on the long range C H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantio-selectivity, whereas the conversion was slightly affected and higher yields were obtained with the R-enantiomers of the alpha-ketols. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.077
• 作为产物：
  描述：

  (S)-(12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid 在 1,4-dithio-D,L-threitol 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (9S,10R,12Z,15Z)-9,10-dihydroxyoctadeca-12,15-dienoic acid 、 (9S,10S,12Z,15Z)-9,10-dihydroxyoctadeca-12,15-dienoic acid
  参考文献：
  名称：

  Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet

  摘要：

  Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity toward Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the alpha-ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereochemistry at the oxymethine carbon was determined based on the long range C H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantio-selectivity, whereas the conversion was slightly affected and higher yields were obtained with the R-enantiomers of the alpha-ketols. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.077

文献信息

• Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet
  作者：Ariaki Murata、Kenji Kai、Ken Tsutsui、Jun Takeuchi、Yasushi Todoroki、Kazuo Furihata、Mineyuki Yokoyama、Susanne Baldermann、Naoharu Watanabe

  DOI：10.1016/j.tet.2012.04.077

  日期：2012.7

  Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10-oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity toward Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the alpha-ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereochemistry at the oxymethine carbon was determined based on the long range C H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantio-selectivity, whereas the conversion was slightly affected and higher yields were obtained with the R-enantiomers of the alpha-ketols. (c) 2012 Elsevier Ltd. All rights reserved.