(9E,11E)-13-oxooctadeca-9,11-dienoic acid | 29623-29-8

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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: (9E,11E)-13-oxooctadeca-9,11-dienoic acid
• 英文别名: (9Z,11E/Z)-13-oxooctadecatrienoic acid；13-oxo-9Z,11E-ODE；13-oxo-9Z,11E/Z-octadecadienoic acid；13-Oxo-9,11-octadecadiensaeure
• CAS: 29623-29-8；31385-09-8；54739-30-9
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: JHXAZBBVQSRKJR-WWYDAZRDSA-N

物化性质

• 沸点：
  425.5±18.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  21.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

制备方法与用途

生物活性

13-Oxo-9E,11E-octadecadienoic acid 是 9-oxo-10,12-octadecadienoic acid 的异构体，是一种有效的 PPARα 激活剂，源自番茄汁。研究显示，13-Oxo-9E,11E-octadecadienoic acid 能降低肥胖糖尿病小鼠的血浆和肝甘油三酯水平。

靶点

PPARα

体内研究

饲喂含有 0.02% 和 0.05% 13-Oxo-9E,11E-octadecadienoic acid 的饲料（4 周）可改善高脂饮食 (HFD) 饲养的 KK-Ay 小鼠的血脂异常，并降低其肝脏和骨骼肌中的甘油三酯含量。具体实验数据如下：

• 动物模型：4 周龄雄性 KK-Ay 小鼠
• 剂量：0.02% 和 0.05%
• 给药方式：饲料，连续 4 周
• 结果：改善了 HFD 饲养的 KK-Ay 小鼠的血脂异常，并降低了肝脏和骨骼肌中的甘油三酯含量。

反应信息

• 作为产物：
  描述：

  13(s)-羟基-9z,11e-十八二烯酸 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以75%的产率得到(9E,11E)-13-oxooctadeca-9,11-dienoic acid
  参考文献：
  名称：

  Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols

  摘要：

  Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these keto compounds to yield back the starting alcohols, but now as racemic mixtures, was also conducted using CeCl3-NaBH4, once again without noticeable modification of the stereochemistry of the double bonds. These reactions proved the usefulness of the chemoenzymatic access to oxylipins through the use of lipoxygenases with various regiospecificity, combined with chemical transformations of the formed hydro(pero)xides. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00087-2

文献信息

• Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols
  作者：Gilles Iacazio

  DOI：10.1016/s0009-3084(03)00087-2

  日期：2003.10

  Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these keto compounds to yield back the starting alcohols, but now as racemic mixtures, was also conducted using CeCl3-NaBH4, once again without noticeable modification of the stereochemistry of the double bonds. These reactions proved the usefulness of the chemoenzymatic access to oxylipins through the use of lipoxygenases with various regiospecificity, combined with chemical transformations of the formed hydro(pero)xides. (C) 2003 Elsevier Ireland Ltd. All rights reserved.