4-羟基-戊烯醛 | 16931-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-羟基-戊烯醛
• 英文名称: 4-hydroxy-2-pentenal
• 英文别名: 4-hydroxy-pent-2-enal；4-Hydroxy-2-pentenal-(1)；4-Hydroxy-2-penten-1-al；4-Hydroxy-2,3-pentenal；4-Hydroxypent-2-en-al；4-Hydroxypent-2-enal
• CAS: 16931-17-2
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: OFWXLYPSGLVHNC-UHFFFAOYSA-N

物化性质

• LogP：
  -0.141 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  L-半胱氨酸 、 4-羟基-戊烯醛 以 水 为溶剂， 反应 12.0h， 生成 (2Ξ,4R)-2-[(2Ξ,3Ξ)-2-((R)-2-amino-2-carboxy-ethylsulfanyl)-3-hydroxy-butyl]-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  半胱氨酸与α，β-不饱和醛的反应

  摘要：

  半胱氨酸在两步反应中加入了丙烯醛，巴豆醛和4-羟基戊烯醛。第一加成产物是β-半胱氨酰基取代的饱和醛1a，1b和3。只能分离通过分子内半缩醛形成稳定的3的单加合物。衍生物1a和1b与另外的半胱氨酸迅速反应，得到噻唑烷化合物2a和2b。而2a和2b即使在醛：半胱氨酸摩尔比≥1的反应中也是唯一的产物，在与羟基戊烯的反应中获得噻唑烷衍生物也需要比率＜1。通过UV，IR和NMR测量，电位滴定，速率定律的确定和元素分析来确定化合物2a，2b，3和4的结构。所有加合物均与半胱氨酸和母体醛保持平衡。估计正向和反向反应的速率常数。正向反应的速率增加约。在2-10的pH范围内，每个pH单位的10倍。

  DOI：

  10.1016/0040-4020(76)87015-9
• 作为产物：
  描述：

  间戊二烯 在 ortho-tungstic acid 双氧水 作用下， 以 叔丁醇 为溶剂， 生成 4-羟基-戊烯醛
  参考文献：
  名称：

  Lonshchakova,T.I. et al., Journal of Organic Chemistry USSR (English Translation), 1979, vol. 15, p. 807 - 811

  摘要：

  DOI：

文献信息

• Kinetik der Reaktion von Sulfhydrylverbindungen mit ?,?-unges�ttigten Aldehyden in w��rigem System
  作者：H. Esterbauer

  DOI：10.1007/bf00909898

  日期：——
• 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.
• Lonshchakova,T.I. et al., Journal of Organic Chemistry USSR (English Translation), 1979, vol. 15, p. 807 - 811
  作者：Lonshchakova,T.I. et al.

  DOI：——

  日期：——
• The reaction of cysteine with α,β-unsaturated aldehydes
  作者：H. Esterbauer、A. Ertl、N. Scholz

  DOI：10.1016/0040-4020(76)87015-9

  日期：1976.1

  and 2b. Whereas 2a and 2b were the only products even in reactions carried out with a molar ratio of aldehyde : cysteine ≧ 1, ratio < 1 was required to obtain a thiazolidine derivative in reactions with hydroxypentenal. The structures of compound 2a, 2b, 3 and 4 were ascertained by means of UV, IR and NMR measurements, potentiometric titrations, determination of the rate laws and elemental analysis.

  半胱氨酸在两步反应中加入了丙烯醛，巴豆醛和4-羟基戊烯醛。第一加成产物是β-半胱氨酰基取代的饱和醛1a，1b和3。只能分离通过分子内半缩醛形成稳定的3的单加合物。衍生物1a和1b与另外的半胱氨酸迅速反应，得到噻唑烷化合物2a和2b。而2a和2b即使在醛：半胱氨酸摩尔比≥1的反应中也是唯一的产物，在与羟基戊烯的反应中获得噻唑烷衍生物也需要比率＜1。通过UV，IR和NMR测量，电位滴定，速率定律的确定和元素分析来确定化合物2a，2b，3和4的结构。所有加合物均与半胱氨酸和母体醛保持平衡。估计正向和反向反应的速率常数。正向反应的速率增加约。在2-10的pH范围内，每个pH单位的10倍。