(E)-4-hydroxy-2-nonenal dimethyl acetal | 109296-10-8

• 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: (E)-4-hydroxy-2-nonenal dimethyl acetal
• 英文别名: 4-hydroxy-2-nonenal dimethylacetal；4-hydroxy-2(E)-nonenal dimethyl acetal；4-hydroxy-2-trans-nonenal dimethylacetal；4-hydroxy-trans-2-nonenal-dimethylacetal；trans-4-hydroxy-2-nonenal dimethylacetal；1,1-dimethoxy-non-2t-en-4-ol；4-HNE-DMA；(E)-4-hydroxynon-2-enal dimethyl acetal；(E)-1,1-dimethoxynon-2-en-4-ol
• CAS: 109296-10-8
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: ATGIHMSJAARJTF-CMDGGOBGSA-N

物化性质

• 沸点：
  278.7±40.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-hydroxy-2-nonenal dimethyl acetal 在 盐酸 、 2,2'-联吡啶 、 camphor-10-sulfonic acid 、 sodium acetate 、 copper(II) sulfate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 10.0h， 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：

  4-bromo-1,1-dimethoxy-non-2t-ene 在 silver(l) oxide 作用下， 以 水 、 丙酮 为溶剂， 生成 (E)-4-hydroxy-2-nonenal dimethyl acetal
  参考文献：
  名称：

  �ber die Wirkungen von Aldehyden auf gesunde und maligne Zellen, 2. Mitt.: Synthese von homologen 4-Hydroxy-2-alkenalen, I

  摘要：

  DOI：

  10.1007/bf01167149

文献信息

• An expeditious synthesis of 4-hydroxy-2(E)-nonenal (4-HNE), its dimethyl acetal and of related compounds
  作者：Laurent Soulère、Yves Queneau、Alain Doutheau

  DOI：10.1016/j.chemphyslip.2007.07.003

  日期：2007.12

  The facile one step synthesis of 4-hydroxy-2E-nonenal and its dimethyl acetal via a cross-metathesis reaction between commercially available octen-3-ol and acrolein or its dimethyl acetal is reported. The method was extended to the synthesis of C6 and C12 4-hydroxy-2E-enals, their dimethyl acetal and of the 4-hydroxy-2E-nonenoic acid (4-HNA).

  据报道，通过可商购的辛烯-3-醇和丙烯醛或其二甲基乙缩醛之间的交叉复分解反应，可以容易地一步合成4-羟基-2E-壬烯醛及其二甲基乙缩醛。该方法扩展到合成C6和C12 4-羟基-2E-烯醛，它们的二甲基乙缩醛和4-羟基-2E-壬烯酸（4-HNA）。
• Synthesis, Physicochemical Characterization, and Biological Activities of New Carnosine Derivatives Stable in Human Serum As Potential Neuroprotective Agents
  作者：Massimo Bertinaria、Barbara Rolando、Marta Giorgis、Gabriele Montanaro、Stefano Guglielmo、M. Federica Buonsanti、Valentina Carabelli、Daniela Gavello、Pier Giuseppe Daniele、Roberta Fruttero、Alberto Gasco

  DOI：10.1021/jm101394n

  日期：2011.1.27

  The synthesis and the physicochemical and biological characterization of a series of carnosine amides bearing on the amido group alkyl substituents endowed with different lipophilicity are described. All synthesized products display carnosine-like properties differentiating from the lead for their high serum stability. They are able to complex Cu2+ ions at physiological pH with the same stoichiometry

  描述了一系列具有不同亲脂性的酰胺基烷基取代基上的肌肽酰胺的合成及其理化和生物学特性。所有合成的产品均具有类似肌肽的特性，因其较高的血清稳定性而不同于铅。它们能够以与肌肽相同的化学计量比在生理pH下络合Cu 2+离子。新合成的化合物显示出高度显着的铜离子螯合能力，并且能够保护LDL免受Cu 2+离子催化的氧化，其中活性最高的化合物是亲水性最高的化合物。所有合成的酰胺都显示出很强的肌肽样HNE猝灭活性；特别是7d，该研究的系列成员之一，能够穿越血脑屏障（BBB）并保护原代小鼠海马神经元免受HNE诱导的死亡。这些产物可被认为是肌肽的代谢稳定的类似物，作为潜在的神经保护剂值得进一步研究。
• Fumaraldehyde monodimethyl acetal: An easily accessible and versatile intermediate.
  作者：R Grée、H Tourbah、R Carrié

  DOI：10.1016/s0040-4039(00)85113-8

  日期：1986.1

  Fumaraldehyde monodimethylacetal 1 is both an easily accessible and versatile polyfunctionnal synthon ; the stereoselective preparation of various lipids from natural origin illustrates some of its synthetic possibilities.

  富马醛单二甲基缩醛1是一种易于获得的多功能合成子; 天然来源的各种脂质的立体选择性制备说明了其一些合成可能性。
• Structural Definition of Early Lysine and Histidine Adduction Chemistry of 4-Hydroxynonenal
  作者：Durgesh V. Nadkarni、Lawrence M. Sayre

  DOI：10.1021/tx00044a014

  日期：1995.3

  could confirm unambiguously the structure of a HNE-His imidazole(N tau) Michael adduct, stabilized as a cyclic hemiacetal and isolated from a neutral aqueous 1:1 stoichiometry reaction mixture. In the case of Lys/amine reactivity, where an excess of amine is needed to avert HNE aldol condensation, the predominance of a 1:1 Michael adduct in homogeneous aqueous solution and a 1:2 Michael-Schiff base

  脂质过氧化产物反式-4-羟基-2-壬烯醛（HNE）与低密度脂蛋白（LDL）的共价修饰有关，被认为可能导致LDL在动脉壁的初期过度积累。动脉粥样硬化。到目前为止，有关“早期”蛋白质侧链修饰的确切结构的建议均基于间接证据。在本文中，通过将NMR光谱性质与手性中心含量降低的模型（在某些情况下是氢化物还原后）相关的NMR光谱性质相关联，阐明了首次形成的基于His和Lys的加合物的结构。以这种方式，我们可以清楚地确认HNE-His咪唑（N tau）Michael加合物的结构，其稳定为环状半缩醛，并从中性水溶液1：1的化学计量反应混合物中分离。在Lys /胺反应性的情况下，为了避免HNE醛缩合需要过量的胺，均相水溶液中1：1的迈克尔加合物和两相水溶液中的1：2的Michael-Schiff碱加合物占优势。 -有机条件可以通过分离相应的硼氢化物还原形式来验证。1：2加合物，被证明以环状半胱氨酸存在，在某
• 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