2-Nonenal, 4-(acetyloxy)-, (2E)- | 37423-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Nonenal, 4-(acetyloxy)-, (2E)-
• 英文别名: 4-acetyloxy-2-(E)-nonenal；4-acetoxy-2(E)-nonenal
• CAS: 37423-49-7
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: ADPNBZQNEJHXCN-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  14.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-Nonenal, 4-(acetyloxy)-, (2E)- 、 (1R,2R)-(+)-N,N-二甲基-1,2-双[3-(三氟醚甲基)苯-1,2-乙烷二胺 在 4 A molecular sieve 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 Acetic acid 1-{(E)-2-[(4R,5R)-1,3-dimethyl-4,5-bis-(3-trifluoromethyl-phenyl)-imidazolidin-2-yl]-vinyl}-hexyl ester
  参考文献：
  名称：

  Chiral trifluoro diamines as convenient reagents for determining the enantiomeric purity of aldehydes by use of fluorine-19 NMR spectroscopy

  摘要：

  DOI：

  10.1021/jo00271a034
• 作为产物：
  描述：

  溶剂黄146 、 3-nonenal 在 copper diacetate 、 manganese triacetate 作用下， 生成 2-Nonenal, 4-(acetyloxy)-, (2E)-
  参考文献：
  名称：

  One-Electron-Transfer Oxidation by Metal Salts. A Convenient Synthesis of γ,δ-Unsaturated Aldehydes

  摘要：

  DOI：

  10.1055/s-1972-21886

文献信息

• 4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5-analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis
  作者：Gerhard Bringmann、Michael Gassen、Raphaëlle Lardy

  DOI：10.1016/s0040-4020(01)81757-9

  日期：1994.8

  A stereoselective synthesis of the lipid peroxidation products 4-hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)-catalyzed oxidative degradation and subsequent stereoanalysis of the resulting alpha-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.
• Synthesis and Cellular Effects of an Intracellularly Activated Analogue of 4-Hydroxynonenal
  作者：M. Diana Neely、Venkataraman Amarnath、Carl Weitlauf、Thomas J. Montine

  DOI：10.1021/tx010115w

  日期：2002.1.1

  4-Hydroxy-2-nonenal (HNE) has been recognized as reactive product of lipid peroxidation and has been suggested to play a role in the pathogenesis in several common diseases as well as injuries caused by environmental toxicants. Although formed intracellularly in vivo, for practical reasons this molecule is applied extracellularly in order to analyze its biological effects. The focus of this study was to develop an approach that would enable intracellular HNE production in the absence of the many other products and processes that occur in cells experiencing generalized oxidative stress. To this end, we synthesized 1,1,4-tris(acetyloxy)-2(E)-nonene (HNE[Ac](3)), a triester analogue of HNE that is itself unreactive but could be hydrolyzed intracellularly presumably by lipases and/or esterases into the highly reactive HNE. In vitro lipase rapidly converted HNE(Ac)(3) initially to 4-acetyloxy-2-nonenal (HNE [Ac](1)) and then to HNE, Neuro 2A cell lysate also caused a rapid hydrolysis of HNE(Ac)(3) into HNE(Ac)(1) and HNE. Incubation of BSA with HNE(Ac)(3) resulted in protein-adduct formation only in the presence of lipase. We demonstrated adduction of HNE to proteins in Neuro 2A cells exposed to HNE(Ac)(3) by immunoblotting and immunocytochemistry using antibodies specific for HNE-Michael adducts on proteins. We have previously shown that microtubule organization is very sensitive to HNE. Analysis of Neuro 2A cell microtubules showed that this cytoplasmic organelle is similarly sensitive to HNE and HNE(Ac)(3).