(8Z,11Z)-5-hydroxy-6-oxotetradeca-8,11-dienoic acid | 1036406-71-9

• 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: (8Z,11Z)-5-hydroxy-6-oxotetradeca-8,11-dienoic acid
• CAS: 1036406-71-9
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: OBBBLHIPCLQFRC-CWWKMNTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8Z,11Z)-5-hydroxy-6-oxotetradeca-8,11-dienoic acid 、 去甲肾上腺素 在 Tris-HCl buffer 、 氧气 作用下， 以 水 为溶剂， 反应 15.0h， 以9.0%的产率得到7-((3R,3aS,4S,5S,7R)-3,7-dihydroxy-8-oxo-4-((Z)-pent-2-en-1-yl)-2,3,4,5,7,8-hexahydro-1H-3a,7-methanooxocino[5,4-b]pyrrol-5-yl)-5-hydroxy-6-oxoheptanoic acid
  参考文献：
  名称：

  Structure–activity relationship study of flowering-inducer FN against Lemna paucicostata

  摘要：

  FN1 (1) and FN2 (2), cycloadducts of alpha-ketol octaclecadienoic acid (3) with norepinephrine (NE), induce flowering in Lemna paucicostata. In order to broaden our understanding of structural requirements of FN for flower induction, nine analogs of 3 (4-12) were synthesized and reacted with NE under basic conditions. These analogs, except for 8, 10, and 12, exhibited significant activity regarding to floral induction in L. paucicostata. Similar experiments were carried out by using 3 and epinephrine, and it was demonstrated that these products also possessed biological activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.115
• 作为产物：
  描述：

  methyl (10Z,13Z)-7-hydroxy-8-oxohexadeca-10,13-dienoate 在 phosphate buffer 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 (8Z,11Z)-5-hydroxy-6-oxotetradeca-8,11-dienoic acid
  参考文献：
  名称：

  Structure–activity relationship study of flowering-inducer FN against Lemna paucicostata

  摘要：

  FN1 (1) and FN2 (2), cycloadducts of alpha-ketol octaclecadienoic acid (3) with norepinephrine (NE), induce flowering in Lemna paucicostata. In order to broaden our understanding of structural requirements of FN for flower induction, nine analogs of 3 (4-12) were synthesized and reacted with NE under basic conditions. These analogs, except for 8, 10, and 12, exhibited significant activity regarding to floral induction in L. paucicostata. Similar experiments were carried out by using 3 and epinephrine, and it was demonstrated that these products also possessed biological activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.115

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.
• Structure–activity relationship study of flowering-inducer FN against Lemna paucicostata
  作者：Kenji Kai、Jun Takeuchi、Taichi Kataoka、Mineyuki Yokoyama、Naoharu Watanabe

  DOI：10.1016/j.tet.2008.04.115

  日期：2008.7

  FN1 (1) and FN2 (2), cycloadducts of alpha-ketol octaclecadienoic acid (3) with norepinephrine (NE), induce flowering in Lemna paucicostata. In order to broaden our understanding of structural requirements of FN for flower induction, nine analogs of 3 (4-12) were synthesized and reacted with NE under basic conditions. These analogs, except for 8, 10, and 12, exhibited significant activity regarding to floral induction in L. paucicostata. Similar experiments were carried out by using 3 and epinephrine, and it was demonstrated that these products also possessed biological activity. (C) 2008 Elsevier Ltd. All rights reserved.