4,5-二氧代戊酸 | 5976-90-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 4,5-二氧代戊酸
• 中文别名: 2-环己烯-1-醇,2-甲基-5-(1-甲基乙烯基)-,1-甲磺酸酯
• 英文名称: 4-formyl-4-oxobutanoic acid
• 英文别名: 4,5-dioxopentanoic acid；4,5-Dioxovaleric acid；4,5-dioxo-valeric acid；4,5-Dioxo-valeriansaeure；γ,δ-Dioxovaleriansaeure；4-Oxo-glutaraldehyd-(5)-saeure
• CAS: 5976-90-9
• 化学式: C₅H₆O₄
• mdl: MFCD05260788
• 分子量: 130.1
• InChiKey: YHUFRVYVNKGICT-UHFFFAOYSA-N

物化性质

• 沸点：
  273.9±23.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-二氧代戊酸 在 溴 作用下， 生成 alpha-酮戊二酸
  参考文献：
  名称：

  Mayer, Biochemische Zeitschrift, 1931, vol. 233, p. 370

  摘要：

  DOI：
• 作为产物：
  描述：

  diethoxyacetyl-succinic acid diethyl ester 在 barium dihydroxide 作用下， 生成 4,5-二氧代戊酸
  参考文献：
  名称：

  Rugeley; Johnson, Journal of the American Chemical Society, 1925, vol. 47, p. 3000

  摘要：

  DOI：

文献信息

• Wolff, Justus Liebigs Annalen der Chemie, 1890, vol. 260, p. 128
  作者：Wolff

  DOI：——

  日期：——
• Watkins, Bruce E.; Knize, Mark G.; Morris, Chuck J., Heterocycles, 1987, vol. 26, # 8, p. 2069 - 2072
  作者：Watkins, Bruce E.、Knize, Mark G.、Morris, Chuck J.、Andresen, Brian D.、Happe, James、et al.

  DOI：——

  日期：——
• Kawai, Nippon Kagaku Zasshi, 1959, vol. 80, p. 1317,1320
  作者：Kawai

  DOI：——

  日期：——
• Fujise, Biochemische Zeitschrift, 1931, vol. 236, p. 241,245
  作者：Fujise

  DOI：——

  日期：——
• DNA Alkylation by 4,5-Dioxovaleric Acid, the Final Oxidation Product of 5-Aminolevulinic Acid
  作者：Thierry Douki、Janice Onuki、Marisa H. G. Medeiros、Etelvino J. H. Bechara、Jean Cadet、Paolo Di Mascio

  DOI：10.1021/tx970157d

  日期：1998.2.1

  The heme precursor 6-aminolevulinic acid (ALA) accumulates under pathological conditions, namely, acute intermittent porphyria (AIP) and tyrosinosis, two diseases that are associated with increased liver cancer incidence. This has been previously linked to an enhanced production of reactive oxygen species generated by a metal-catalyzed ALA oxidation process, which was shown to cause DNA single-strand breaks and guanine oxidation within both isolated and cellular DNA. In the present work, we established that the final oxidation product of ALA, 4,5-dioxovaleric acid (DOVA), is an efficient alkylating agent of the guanine moieties within both nucleoside and isolated DNA. Adducts were produced through the formation of a Schiff base involving the N-2-amino group of 2'-deoxyguanosine (dGuo) and the ketone function of DOVA, respectively. The modified dGuo nucleosides were characterized, following reduction into stable secondary amines, by extensive NMR, infrared, and mass spectrometry analyses. A method, based on the use of HPLC with electrochemical detection, was then developed for the sensitive measurement of the DOVA-dGuo adducts. Using this assay, we showed that the guanine moieties of isolated DNA can undergo the same reaction as the free nucleoside. The present data provide additional information on the genotoxic potential of ALA and reinforce the hypothesis that AIP may be involved in the induction of primary liver cell carcinoma.