alpha-Methyleicosapentaenoic 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: alpha-Methyleicosapentaenoic acid
• 英文别名: 2-methyleicosa-5,8,11,14,17-pentaenoic acid；(5Z,8Z,11Z,14Z,17Z)-2-methylicosa-5,8,11,14,17-pentaenoic acid
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: BUKFSVVYYMDFME-JEBPEJKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  EPA乙酯 在 lithium hydroxide 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 0.5h， 生成 alpha-Methyleicosapentaenoic acid
  参考文献：
  名称：

  α- and β- alkyl-substituted eicosapentaenoic acids

  摘要：

  alpha-ethyl-, alpha-methyl- and beta-methyl eicosapentaenoic acid (EPA) were prepared and their incorporation into cell lipids and effects on eicosanoid synthesis compared with EPA and docosahexaenoic acid (DHA). alpha- and beta-methyl EPA were incorporated into hepatocyte triacylglycerols as efficiently as EPA, whereas lesser amounts were found in phospholipids. alpha-ethyl EPA was not incorporated into phospholipids but small amounts were detected in triacylglycerol. All derivatives inhibited the synthesis of arachidonic acid, although less efficiently than EPA and DHA. The derivatives were poor substrates of prostaglandin H (PGH) synthase and 5-lipoxygenase, and they all inactivated PGH synthase. In isolated platelets, alpha-methyl EPA was a stronger inhibitor of TxB(2) production than EPA, alpha-ethyl- and beta-methyl EPA. All derivatives were stronger inducers of peroxisomal beta-oxidation than EPA and DHA. This increased induction probably is a consequence of the blocked mitochondrial beta-oxidation of the derivatives. (C) 1998 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(97)00497-8

文献信息

• ALPHA-SUBSTITUTED OMEGA-3 LIPIDS THAT ARE ACTIVATORS OR MODULATORS OF THE PEROXISOME PROLIFERATORS-ACTIVATED RECEPTOR (PPAR).
  申请人：Pronova BioPharma Norge AS

  公开号：EP2094640A1

  公开（公告）日：2009-09-02
• JP2010508259A
  申请人：——

  公开号：JP2010508259A

  公开（公告）日：2010-03-18
• Novel Compounds
  申请人：Bryhn Morten

  公开号：US20080300306A1

  公开（公告）日：2008-12-04

  Compounds of formula (I); wherein R 1 and R 2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl-DHA, alpha-methyl DHA methyl ester, alpha-methyl-DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed. The use of such compounds as medicaments, in particular for the treatment of diabetes type 2, is also disclosed.
• FATTY ACID ANALOGUES, I.E. INCLUDING DHA DERIVATIVES FOR USES AS A MEDICAMENT
  申请人：Bryhn Morten

  公开号：US20090203778A1

  公开（公告）日：2009-08-13

  A compound of formula (I) wherein R 1 and R 2 are different and each is chosen from a methyl group and a hydrogen atom; wherein X is chosen from a carboxylic acid group, a carboxylate group, a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex, or pro-drug of said compound. A pharmaceutical composition and a lipid composition comprising a compound of formula (I) is also disclosed. A method for the treatment of obesity, diabetes mellitus, amyloidos-related diseases, cardiovascular-diseases, and cerebrovascular diseases is also disclosed.
• ALPHA-SUBSTITUTED OMEGA-3 LIPIDS THAT ARE ACTIVATORS OR MODULATORS OF THE PEROXISOME PROLIFERATORS-ACTIVATED RECEPTOR (PPAR)
  申请人：Bryhn Morten

  公开号：US20100035990A1

  公开（公告）日：2010-02-11

  Omega-3 lipid compounds of the general formula (I): wherein R 1 and R 2 are the same or different and may be selected from a group of substituents consisting of hydrogen, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; X represents a carboxylic acid or a derivative thereof, a carboxylate, a carboxylic anhydride or a carboxamide; and Y is a C 6 to C 22 alkene with two or more double bonds, having E and/or Z configuration, are disclosed. Also disclosed are pharmaceutical compositions and lipid compositions comprising such compounds, and to such compounds for use as medicaments in particular for the treatment of cardiovascular and metabolic diseases.