4,5-epoxydocosapentaenoic acid

• 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: 4,5-epoxydocosapentaenoic acid
• 英文别名: 3-[3-[(2Z,5Z,8Z,11Z,14Z)-heptadeca-2,5,8,11,14-pentaenyl]oxiran-2-yl]propanoic acid
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: AOGOYVLLUIASTK-JLNKQSITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-epoxydocosapentaenoic acid 以 氯仿 为溶剂， 反应 24.0h， 以54 mg的产率得到5-[(3Z,6Z,9Z,12Z,15Z)-1-hydroxyoctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone
  参考文献：
  名称：

  Synthesis of docosahexaenoic acid derivatives designed as novel PPARγ agonists and antidiabetic agents

  摘要：

  To discover novel peroxisome proliferator-activated receptor gamma (PPAR gamma) agonists that Could be used as antidiabetic agents, we designed docosahexacnoic acid (DHA) derivatives (2 and 3), which have a hydrophilic substituent at the C(4)-position, based on the crystal structure of the ligand-binding pocket of PPAR gamma. These compounds were synthesized via iodolactolic as a key intermediate. We found that both DHA derivatives (2 and 3) showed PPAR gamma transactivation higher than, or comparable to, that of pioglitazone, which is a TZD derivative used as an antidiabetic agent. DHA derivatives related to these potent Compounds 2 and 3 were also synthesized to study structure-activity relationships. Furthermore, 4-OH DHA 2, which shows strong PPAR gamma transcriptional activity, was separated as an optically pure form. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.074
• 作为产物：
  描述：

  二十二碳六烯酸 在 2,4,6-三甲基吡啶 、 lithium hydroxide 、 碘 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 4,5-epoxydocosapentaenoic acid
  参考文献：
  名称：

  Synthesis of docosahexaenoic acid derivatives designed as novel PPARγ agonists and antidiabetic agents

  摘要：

  To discover novel peroxisome proliferator-activated receptor gamma (PPAR gamma) agonists that Could be used as antidiabetic agents, we designed docosahexacnoic acid (DHA) derivatives (2 and 3), which have a hydrophilic substituent at the C(4)-position, based on the crystal structure of the ligand-binding pocket of PPAR gamma. These compounds were synthesized via iodolactolic as a key intermediate. We found that both DHA derivatives (2 and 3) showed PPAR gamma transactivation higher than, or comparable to, that of pioglitazone, which is a TZD derivative used as an antidiabetic agent. DHA derivatives related to these potent Compounds 2 and 3 were also synthesized to study structure-activity relationships. Furthermore, 4-OH DHA 2, which shows strong PPAR gamma transcriptional activity, was separated as an optically pure form. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.074

文献信息

• 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。
• VANROLLINS, MIKE;FRADE, PETER D.;CARRETERO, OSCAR A., J. LIPID RES., 30,(1989) N, C. 275-286
  作者：VANROLLINS, MIKE、FRADE, PETER D.、CARRETERO, OSCAR A.

  DOI：——

  日期：——
• STABLE ANALOGS OF CYP450 LIPID METABOLITES AND INHIBITORS OF SOLUBLE EPOXIDE HYDROLASE
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：EP3377056B1

  公开（公告）日：2020-09-23
• US7091369B2
  申请人：——

  公开号：US7091369B2

  公开（公告）日：2006-08-15