13-oxo-cis-9-octadecenoic acid methyl ester | 26340-70-5

• 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: 13-oxo-cis-9-octadecenoic acid methyl ester
• 英文别名: 13-Oxo-oelsaeure-methylester
• CAS: 26340-70-5
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: TXEXNAOTBRQJTA-NTMALXAHSA-N

物化性质

• 沸点：
  406.8±28.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

反应信息

• 作为产物：
  描述：

  13-hydroxy-cis-9-octadecenoic 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 13-oxo-cis-9-octadecenoic acid methyl ester
  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

文献信息

• Arrestants to<i>Oryzaephilus surinamensis</i>L. from Wheat Flour Infested by the Same Weevil
  作者：Shuhei Nakajima、Keiji Sugawara、Taro Takeda、Masaya Tateishi、Aiko Okamura、Junkichi Iwasa、Naomichi Baba

  DOI：10.1271/bbb.60.1546

  日期：1996.1

  From a hexane extract of wheat flour infested by the sawtoothed grain beetle [Oryzaephilus surinamensis (L.); Coleoptera; Silvanidae], two compounds having arrestive activity were isolated and identified as 13-oxo-cis-9-octadecenoic acid and 15-oxo-cis-11-icosenoic acid.