2-ethyleicosa-5,8,11,14,17-pentaenoic acid | 285977-69-7

• 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: 2-ethyleicosa-5,8,11,14,17-pentaenoic acid
• 英文别名: (all-Z)-2-ethyl-5,8,11,14,17-eicosapentaenoic acid；(5Z,8Z,11Z,14Z,17Z)-2-ethylicosa-5,8,11,14,17-pentaenoic acid
• CAS: 285977-69-7
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: LNPJFFYITCWQDB-AAQCHOMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甘油 、 2-ethyleicosa-5,8,11,14,17-pentaenoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 以58%的产率得到1,2,3-tris((all-Z)-2-ethyl-5,8,11,14,17-eicosapentaenoyl)-sn-glycerol
  参考文献：
  名称：

  WO2008/53331

  摘要：

  公开号：
• 作为产物：
  描述：

  EPA乙酯 在 正丁基锂 、 水 、 二异丙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 19.0h， 生成 2-ethyleicosa-5,8,11,14,17-pentaenoic acid
  参考文献：
  名称：

  [EN] LIPID COMPOUNDS AND COMPOSITIONS AND THEIR OPTHALMIC USE
  [FR] COMPOSÉS LIPIDIQUES ET COMPOSITIONS ASSOCIÉES ET LEUR UTILISATION OPHTALMIQUE

  摘要：

  本发明涉及用于预防或治疗如视网膜退行性疾病和眼部炎症疾病的眼科疾病的一类脂质化合物公式(I)及其药用可接受盐：(I)（其中R1为C9至C22的烷基或具有1至6个双键的C9至C22的烯基；R2选自卤素原子、羟基、烷基、烷氧基、烷硫基、羧基、酰基、氨基和烷基氨基的组；R3为氢原子或R2基团；R4为羧酸或其衍生物；X为亚甲基(-CH2-)，或氧或硫原子）。

  公开号：

  WO2017093732A1

文献信息

• α- and β- alkyl-substituted eicosapentaenoic acids
  作者：Laila N. Larsen、Jon Bremer、Solveig Flock、Lars Skattebøl

  DOI：10.1016/s0006-2952(97)00497-8

  日期：1998.2

  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.
• 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
• OMEGA-3 LIPID COMPOUNDS
  申请人：Pronova Biopharma Norge AS

  公开号：EP2102139A2

  公开（公告）日：2009-09-23
• LIPID COMPOUNDS AND COMPOSITIONS AND THEIR OPTHALMIC USE
  申请人：Biozep AS

  公开号：EP3383380A1

  公开（公告）日：2018-10-10
• 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.