3-Oxopropanoic acid

Last updated
3-Oxopropanoic acid
3-oxopropanoic acid.svg
Names
Preferred IUPAC name
3-Oxopropanoic acid
Other names
malonic semialdehyde, formylacetic acid, 3-oxopropanoate
Identifiers
3D model (JSmol)
1741700
ChEBI
ChemSpider
164397
KEGG
PubChem CID
UNII
  • InChI=1S/C3H3O3/c4-2-1-3(5)6/h1H2,(H,5,6)/q-1
    Key: HBHVBGOPNWLCDZ-UHFFFAOYSA-N
  • C([C-]=O)C(=O)O
Properties
C3H4O3
Molar mass 88.062 g·mol−1
Density 1.258 g/cm3
Boiling point 237.3 °C (459.1 °F; 510.4 K)
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
Flash point 111.6 °C [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Oxopropanoic acid (also malonic semialdehyde or formylacetic acid) is an organic chemical compound that carries both a carboxylic acid function and an aldehyde function.

Contents

Natural occurrence

In nature, 3-oxopropanoic acid occurs as a metabolic intermediate. It is formed, for example, by the reversible oxidation of 3-hydroxypropionyl-CoA with nicotinamide adenine dinucleotide (NAD). [3]

A bacterial strain of the species Pseudomonas fluorescens is known to survive on propiolic acid as its sole carbon and energy source. 3-Oxopropanoic acid is an important metabolic intermediate: it is formed by hydration of acetylenic acid and is converted into acetyl-CoA by decarboxylation. [4] It also occurs as a metabolic intermediate in a strain of Escherichia coli that can grow on uracil as its sole nitrogen source. [5]

3-Oxopropanoic acid also occurs in atmospheric aerosols along with various other organic acids (especially oxalic acid). It has been detected as an aerosol component at various stations during a circumnavigation of the globe by ship. [6] The compound has also been found in aerosol analyses in the Arctic, [7] the North Pacific, [8] India, [9] and Tokyo. [10]

Synthesis

3-Oxopropanoic acid is highly reactive. It is often generated in situ by reacting malic acid with concentrated sulfuric acid. This process releases formic acid, water, and carbon monoxide. [11]

A readily storable precursor to the compound is ethyl 3-oxopropionate diethyl acetal. This can be prepared by condensation of ethyl acetate and ethyl formate, followed by acetalization with hydrogen chloride in absolute ethanol. The 3-oxopropanoic acid can also be obtained from it by hydrolysis with dilute sulfuric acid followed by neutralization.

Reactions

Reaction with a phenol yields coumarin. The enol form, which is initially formed during the preparation from malic acid and sulfuric acid, can condense with urea to form uracil. [11]

Isocytosine was prepared analogously, using guanidine hydrochloride instead of urea. [12]

References

  1. ↑ "SAFETY DATA SHEET" (PDF). BLD Pharm. Retrieved 17 June 2025.
  2. ↑ "3-oxopropanoic acid". chemsrc.com. Retrieved 17 June 2025.
  3. ↑ Den, Halina; Robinson, William G.; Coon, Minor J. (July 1959). "Enzymatic Conversion of β-Hydroxypropionate to Malonic Semialdehyde". Journal of Biological Chemistry . 234 (7): 1666–1671. doi: 10.1016/S0021-9258(18)69904-1 . PMID   13672942 . Retrieved 17 June 2025.
  4. ↑ Yamada, Esther W.; Jakoby, William B. (March 1960). "Aldehyde Oxidation". Journal of Biological Chemistry . 235 (3): 589–594. doi: 10.1016/S0021-9258(19)67910-X . Retrieved 17 June 2025.
  5. ↑ Kim, Kwang-Seo; Pelton, Jeffrey G.; Inwood, William B.; Andersen, Ulla; Kustu, Sydney; Wemmer, David E. (15 August 2010). "The Rut Pathway for Pyrimidine Degradation: Novel Chemistry and Toxicity Problems". Journal of Bacteriology . 192 (16): 4089–4102. doi:10.1128/JB.00201-10. PMC   2916427 . PMID   20400551.
  6. ↑ Fu, Pingqing; Kawamura, Kimitaka; Usukura, Kouichi; Miura, Kazuhiko (20 January 2013). "Dicarboxylic acids, ketocarboxylic acids and glyoxal in the marine aerosols collected during a round-the-world cruise". Marine Chemistry. 148: 22–32. Bibcode:2013MarCh.148...22F. doi:10.1016/j.marchem.2012.11.002. hdl: 2115/52117 . ISSN   0304-4203 . Retrieved 17 June 2025.
  7. ↑ Kawamura, Kimitaka; Kasukabe, Hideki; Barrie, Leonard A. (May 1996). "Source and reaction pathways of dicarboxylic acids, ketoacids and dicarbonyls in arctic aerosols: One year of observations" . Atmospheric Environment . 30 (10–11): 1709–1722. Bibcode:1996AtmEn..30.1709K. doi:10.1016/1352-2310(95)00395-9 . Retrieved 17 June 2025.
  8. ↑ Kawamura, Kimitaka; Usukura, Kouichi (1 May 1993). "Distributions of low molecular weight dicarboxylic acids in the North Pacific aerosol samples" . Journal of Oceanography. 49 (3): 271–283. Bibcode:1993JOce...49..271K. doi:10.1007/BF02269565. ISSN   1573-868X . Retrieved 17 June 2025.
  9. ↑ Pavuluri, Chandra Mouli; Kawamura, Kimitaka; Swaminathan, T. (2010). "Water-soluble organic carbon, dicarboxylic acids, ketoacids, and α-dicarbonyls in the tropical Indian aerosols". Journal of Geophysical Research: Atmospheres . 115 (D11). Bibcode:2010JGRD..11511302P. doi:10.1029/2009JD012661. ISSN   2156-2202 . Retrieved 17 June 2025.
  10. ↑ Kawamura, Kimitaka; Yasui, Osamu (1 March 2005). "Diurnal changes in the distribution of dicarboxylic acids, ketocarboxylic acids and dicarbonyls in the urban Tokyo atmosphere" . Atmospheric Environment . 39 (10): 1945–1960. Bibcode:2005AtmEn..39.1945K. doi:10.1016/j.atmosenv.2004.12.014. ISSN   1352-2310 . Retrieved 17 June 2025.
  11. 1 2 Davidson, David; Baudisch, Oskar (1 September 1926). "The Preparation of Uracil from Urea" . Journal of the American Chemical Society . 48 (9): 2379–2383. Bibcode:1926JAChS..48.2379D. doi:10.1021/ja01420a020. ISSN   0002-7863 . Retrieved 17 June 2025.
  12. ↑ Caldwell, William T.; Kime, Harry B. (1 September 1940). "A New Synthesis of Isocytosine" . Journal of the American Chemical Society . 62 (9): 2365. Bibcode:1940JAChS..62.2365C. doi:10.1021/ja01866a028. ISSN   0002-7863 . Retrieved 17 June 2025.
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