(12Z,15Z)-methyl 10-oxooctadeca-12,15-dienoate | 1036406-96-8

• 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: (12Z,15Z)-methyl 10-oxooctadeca-12,15-dienoate
• CAS: 1036406-96-8
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: XSOOONPJHFTQDC-XJJAZQAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  22.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (12Z,15Z)-methyl 10-oxooctadeca-12,15-dienoate 在 phosphate buffer 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以71%的产率得到(12Z,15Z)-10-oxooctadeca-12,15-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
• 作为产物：
  描述：

  (S)-10-hydroxy-cis-12-cis-15-octadecadienoic acid 在 conjugated linoleic acid dehydrogenase 、 nicotinamide adenine dinucleotide 、 bovine serum albumin 作用下， 以 正己烷 为溶剂， 反应 0.75h， 生成 (12Z,15Z)-methyl 10-oxooctadeca-12,15-dienoate
  参考文献：
  名称：

  Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

  摘要：

  Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD(+)-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with alpha- or beta-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 mu M with a k(cat) of 7.6 x 10(-3) s(-1). The apparent K-m value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 mu M with a k(cat) of 5.7 x 10(-1) s(-1). In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.03.020