()17(18)-EpETE methyl ester | 141339-46-0

• 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: ()17(18)-EpETE methyl ester
• 英文别名: 5,8,11,14-Hexadecatetraenoic acid, 16-(3-ethyloxiranyl)-, methyl ester；(5Z,8Z,11Z,14Z)-eicosatetraenoic acid；(Z)-17,18-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoate
• CAS: 141339-46-0；149342-86-9
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: WXPZUUKQJWLIOW-GZDWWAIGSA-N

物化性质

• 沸点：
  425.1±45.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50mg/mL； DMSO：50mg/mL；乙醇：50mg/mL； PBS（pH 7.2）：1 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  24.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ()17(18)-EpETE methyl ester 在 氢氧化钾 、 sodium acetate 、 溶剂黄146 作用下， 生成 17,18-DiHETE
  参考文献：
  名称：

  Selective terminal olefin oxidation of n-3 polyunsaturated fatty acids

  摘要：

  Through the action of N-bromosuccinimide in aqueous glyme, terminal double bond of n-3 fatty acids was selectively converted to the corresponding bromohydrin. This evidence suggests the tight conformation of the n-3 fatty acids in aqueous medium.

  DOI：

  10.1016/s0040-4039(00)91651-4
• 作为产物：
  描述：

  重氮甲烷 、 全顺式二十碳五烯酸 生成 ()17(18)-EpETE methyl ester
  参考文献：
  名称：

  Selective terminal olefin oxidation of n-3 polyunsaturated fatty acids

  摘要：

  Through the action of N-bromosuccinimide in aqueous glyme, terminal double bond of n-3 fatty acids was selectively converted to the corresponding bromohydrin. This evidence suggests the tight conformation of the n-3 fatty acids in aqueous medium.

  DOI：

  10.1016/s0040-4039(00)91651-4

文献信息

• Biocatalytic regio- and stereoselective access to ω-3 endocannabinoid epoxides with peroxygenase from oat flour
  作者：Claudia Sanfilippo、Angela Patti

  DOI：10.1016/j.bioorg.2021.105014

  日期：2021.8

  ethanolamides of ω-3 fatty acids EPA and DHA, regarded as biologically active ω-3 endocannabinoids, in the presence of a peroxygenase-containing preparation from oat flour was investigated. Good regio- and steroselectivity toward the formation of the epoxide on the terminal double bond in the chain was observed with both these fatty acid derivatives and chiral monoepoxides 1 or 2 in 74% optical purity and 51–53%

  研究了 ω-3 脂肪酸 EPA 和 DHA 乙醇酰胺的生物催化环氧化反应，被认为是具有生物活性的 ω-3 内源性大麻素，在含有过氧化酶的燕麦粉制剂存在下进行了研究。观察到这些脂肪酸衍生物和手性单环氧化物1或2对在链中末端双键上形成环氧化物具有良好的区域选择性和立体选择性分离出 74% 的光学纯度和 51-53% 的产率并进行光谱表征。在反应介质中使用丙酮作为共溶剂可以将起始底物的浓度增加至 40 mM，并进一步提高 DHA-EA 环氧化的选择性。由于酶制剂的容易获得，该方法为获得脂肪酸的氧官能化衍生物提供了一种有价值的策略。
• Trans Fatty Acids: Chemical Synthesis of Eicosapentaenoic Acid Isomers and Detection in Rats Fed a Deodorized Fish Oil Diet
  作者：Carla Ferreri、Stanislav A. Grabovskiy、Manar Aoun、Michele Melchiorre、Natalia Kabal’nova、Christine Feillet-Coudray、Gilles Fouret、Charles Coudray、Chryssostomos Chatgilialoglu

  DOI：10.1021/tx200467c

  日期：2012.3.19

  Eicosapentaenoic acid (EPA) is a polyunsaturated fatty acid present in fish oils used for omega-3 enriched diets. The natural cis double bond geometry can be transformed to the trans configuration during the deodorization process utilized in the food industry. The analytical discrimination of the possible five monotrans regioisomers represents a limiting step for the recognition and structure-activity relationship in connection with the harmful effects of trans fatty acids in health. We carried out a dual synthetic strategy, providing new access to monotrans EPA isomers and valuable information on GC and NMR characteristics for further applications in metabolomics and lipidomics. This small library was used as an analytical reference for isomer determination in deodorized fish oils and the follow-up of rats fed fish oil diets, evidencing for the first time that monotrans EPA isomers are incorporated in liver mitochondrial membranes after dietary intake.