(E)-1,1-dimethoxy-2-nonen-4-one | 194291-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,1-dimethoxy-2-nonen-4-one
• 英文别名: 4-oxo-2-nonenal dimethylacetal；1,1-dimethoxynon-2-en-4-one；(E)-1,1-dimethoxynon-2-en-4-one
• CAS: 194291-91-3
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: RDRGCXRHCIJXRS-CMDGGOBGSA-N

物化性质

• 沸点：
  285.8±40.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1,1-dimethoxy-2-nonen-4-one 在 盐酸 、 2,2'-联吡啶 、 camphor-10-sulfonic acid 、 copper(II) sulfate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Independent Synthesis, Solution Behavior, and Studies on the Mechanism of Formation of a Primary Amine-Derived Fluorophore Representing Cross-linking of Proteins by (E)-4-Hydroxy-2-nonenal

  摘要：

  Lipid peroxidation in aging and degenerative disease results in the production of 4-hydroxy-2-alkenals that modify proteins and give rise to both protein cross-linking and fluorophore generation. Recent model studies demonstrated that the major ex/em 360/430 fluorophore formed from (E)-4-hydroxy-2-nonenal (HNE) or (E)-4-hydroxy-2-hexenal (HHE) and protein lysine-based amine is a 2-alkyl-2-hydroxy-1,2-dihydropyrrol-3-one iminium 1:2 cross-link (1), a structure that is further confirmed here using N-15-labeling, and which has pH stability characteristics the same as those of lipofuscin pigments isolated from human tissues. Fluorophore generation represents an overall four-electron oxidation, requires dioxygen, and is enhanced by the presence of Cu(II). The HNE-propylamine-derived fluorophore 1a was independently synthesized from either 3,4-dioxononanal (8) or (E)-4-oxo-2-nonenal (13), providing further evidence for its assigned structure and clues to how it forms from HNE. Mechanistic studies on HNE-derived fluorophore formation permit ruling out the initial reversible HNE-derived Schiff base Michael adduct (17) as an intermediate. In addition, the structurally related non-cross-link 2-pentyl-2-hydroxy-1,2-dihydropyrrol-3-one 9a that forms along with 1a from 8 does not form from HNE and does: not serve as a precursor to la in the HNE-amine reaction system. A mechanism involving two 2e oxidations following initial Schiff base formation is proposed that is consistent with intermediates independently accessed from 8 and 13.

  DOI：

  10.1021/jo982523j
• 作为产物：
  描述：

  (E)-4-hydroxy-2-nonenal dimethyl acetal 在 manganese(IV) oxide 作用下， 生成 (E)-1,1-dimethoxy-2-nonen-4-one
  参考文献：
  名称：

  在细菌硝基还原酶的存在下，由2,4-二硝基苯酚和1,3-二硝基py体外合成1，N6-etheno-2'-脱氧腺苷和1，N2-etheno-2'-脱氧鸟苷。

  摘要：

  共价硝基-PAH DNA加合物的形成和硝基-PAH介导的氧化损伤是引发硝基-PAH致癌的两种可能机制。将1,3-二硝基py（100 microM）或1,4-二硝基苯酚（100 microM）与150 microM NADH，0.5单位大肠杆菌硝基还原酶，100 microM亚油酸，0.5 mM亚铁的混合物孵育60分钟通过液相色谱多级质谱法分析了100μM2′-脱氧腺苷（2′-dA）或100μM2′-脱氧鸟苷（2′-dG）。1，N（6）-etheno-2'-脱氧腺苷（epsilondA）加4-oxo-2-壬烯醛（4-ONE）和1，N（2）-etheno-2'-脱氧鸟苷（epsilondG）加4的混合物-可以分别从2'-dA和2'-dG中检测到一个。添加2％的丙醇会抑制乙炔加合物的形成。dA和dG的消失动力学分析表明，与dA相比，dG被更快地消除（dG和dA分别为t1 / 2 ＝ 23.3min和98

  DOI：

  10.1002/tox.20253

文献信息

• 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).
• Independent Synthesis, Solution Behavior, and Studies on the Mechanism of Formation of a Primary Amine-Derived Fluorophore Representing Cross-linking of Proteins by (<i>E</i>)-4-Hydroxy-2-nonenal
  作者：Guozhang Xu、Yahua Liu、Lawrence M. Sayre

  DOI：10.1021/jo982523j

  日期：1999.8.1

  Lipid peroxidation in aging and degenerative disease results in the production of 4-hydroxy-2-alkenals that modify proteins and give rise to both protein cross-linking and fluorophore generation. Recent model studies demonstrated that the major ex/em 360/430 fluorophore formed from (E)-4-hydroxy-2-nonenal (HNE) or (E)-4-hydroxy-2-hexenal (HHE) and protein lysine-based amine is a 2-alkyl-2-hydroxy-1,2-dihydropyrrol-3-one iminium 1:2 cross-link (1), a structure that is further confirmed here using N-15-labeling, and which has pH stability characteristics the same as those of lipofuscin pigments isolated from human tissues. Fluorophore generation represents an overall four-electron oxidation, requires dioxygen, and is enhanced by the presence of Cu(II). The HNE-propylamine-derived fluorophore 1a was independently synthesized from either 3,4-dioxononanal (8) or (E)-4-oxo-2-nonenal (13), providing further evidence for its assigned structure and clues to how it forms from HNE. Mechanistic studies on HNE-derived fluorophore formation permit ruling out the initial reversible HNE-derived Schiff base Michael adduct (17) as an intermediate. In addition, the structurally related non-cross-link 2-pentyl-2-hydroxy-1,2-dihydropyrrol-3-one 9a that forms along with 1a from 8 does not form from HNE and does: not serve as a precursor to la in the HNE-amine reaction system. A mechanism involving two 2e oxidations following initial Schiff base formation is proposed that is consistent with intermediates independently accessed from 8 and 13.
• In vitro synthesis of 1,N6-etheno-2′-deoxyadenosine and 1,N2-etheno-2′-deoxyguanosine by 2,4-dinitrophenol and 1,3-dinitropyrene in presence of a bacterial nitroreductase
  作者：Serge Chiron、Stéphane Barbati、Michel De Méo、Alain Botta

  DOI：10.1002/tox.20253

  日期：2007.4

  incubation of 1,3-dinitropyrene (100 microM) or 1,4-dinitrophenol (100 microM) with a mixture of 150 microM NADH, 0.5 units of E. coli nitroreductase, 100 microM linoleic acid, 0.5 mM ferrous iron, and 100 microM 2'-deoxyadenosine (2'-dA) or 100 microM 2'-deoxyguanosine (2'-dG) were analyzed by liquid chromatography multistage mass spectrometry. Mixtures of 1,N(6)-etheno-2'-deoxyadenosine (epsilondA)

  共价硝基-PAH DNA加合物的形成和硝基-PAH介导的氧化损伤是引发硝基-PAH致癌的两种可能机制。将1,3-二硝基py（100 microM）或1,4-二硝基苯酚（100 microM）与150 microM NADH，0.5单位大肠杆菌硝基还原酶，100 microM亚油酸，0.5 mM亚铁的混合物孵育60分钟通过液相色谱多级质谱法分析了100μM2′-脱氧腺苷（2′-dA）或100μM2′-脱氧鸟苷（2′-dG）。1，N（6）-etheno-2'-脱氧腺苷（epsilondA）加4-oxo-2-壬烯醛（4-ONE）和1，N（2）-etheno-2'-脱氧鸟苷（epsilondG）加4的混合物-可以分别从2'-dA和2'-dG中检测到一个。添加2％的丙醇会抑制乙炔加合物的形成。dA和dG的消失动力学分析表明，与dA相比，dG被更快地消除（dG和dA分别为t1 / 2 ＝ 23.3min和98