Methyl (all-Z)-5,6-epoxyicosa-8,11,14,17-tetraenoate | 234087-57-1

• 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: Methyl (all-Z)-5,6-epoxyicosa-8,11,14,17-tetraenoate
• 英文别名: 5(6)-EpETE methyl ester；methyl 4-[3-[(2Z,5Z,8Z,11Z)-tetradeca-2,5,8,11-tetraenyl]oxiran-2-yl]butanoate
• CAS: 234087-57-1
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: BDSCYYACNUKQLZ-GJDCDIHCSA-N

物化性质

• 沸点：
  421.6±40.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl (all-Z)-5,6-epoxyicosa-8,11,14,17-tetraenoate 在 六甲基磷酰三胺 、 copper(l) iodide 、 正丁基锂 、 二异丁基氢化铝 、 高碘酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 顺6,9,12,15-十八碳四烯酸
  参考文献：
  名称：

  Concise syntheses of three ω-3 polyunsaturated fatty acids

  摘要：

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.009
• 作为产物：
  描述：

  全顺式二十碳五烯酸 在 碘 、 potassium hydrogencarbonate 、 potassium iodide 、 potassium carbonate 作用下， 以 水 、 甲醇 为溶剂， 以64%的产率得到Methyl (all-Z)-5,6-epoxyicosa-8,11,14,17-tetraenoate
  参考文献：
  名称：

  Concise syntheses of three ω-3 polyunsaturated fatty acids

  摘要：

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.009

文献信息

• Syntheses of some polyunsaturated trifluoromethyl ketones as potential phospholipase A2 inhibitors
  作者：Anne Kristin Holmeide、Lars Skattebøl

  DOI：10.1039/b001944p

  日期：——

  Starting from (all-Z)-icosa-5,8,11,14,17-pentaenoic acid [(all-Z)-eicosa-5,8,11,14,17-pentaenoic acid, EPA] and (all-Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA) several trifluoromethyl ketones, containing sulfur or oxygen atoms at the β-position, have been synthesized as potential inhibitors of cytosolic phospholipase A2. As part of this work EPA and DHA have been oxidatively degraded to (all-Z)-pentadeca-3,6,9,12-tetraenal and (all-Z)-octadeca-3,6,9,12,15-pentaenal, respectively, in 75% overall yields.

  从（全-Z）-5,8,11,14,17-二十碳五烯酸[（全-Z）-5,8,11,14,17-二十碳五烯酸，EPA]和（全-Z）-4,7,10,13,16,19-二十二碳六烯酸（DHA）出发，已经合成了几种含有硫或氧原子在β位的三氟甲基酮，这些化合物被认为是细胞质磷脂酶A2的潜在抑制剂。作为这项工作的一部分，EPA和DHA分别被氧化降解为（全-Z）-3,6,9,12-十五碳四烯醛和（全-Z）-3,6,9,12,15-十八碳五烯醛，总产率均为75%。
• Synthesis of polyconjugated fatty acids
  申请人：Smith William

  公开号：US20050014826A1

  公开（公告）日：2005-01-20

  The present invention relates to fatty acids. In particular, the present invention provides polyconjugated fatty acids, and methods of their synthesis and their use.

  本发明涉及脂肪酸。具体来说，本发明提供了多共轭脂肪酸，以及它们的合成方法和用途。
• Synthesis of juniperonic acid
  作者：Anders Vik、Trond Vidar Hansen、Anne Kristin Holmeide、Lars Skattebøl

  DOI：10.1016/j.tetlet.2010.03.085

  日期：2010.5

  Synthesis of juniperonic acid [(all-Z)-5,11,14,17-eicosatetraenoic acid], has been achieved in eight steps and in 19% overall yield starting from eicosapentaenoic acid. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• Concise syntheses of three ω-3 polyunsaturated fatty acids
  作者：Martin Gjerde Jakobsen、Anders Vik、Trond Vidar Hansen

  DOI：10.1016/j.tetlet.2012.08.009

  日期：2012.10

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.