3-Oxopropanoic acid
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| Names | |
|---|---|
| Preferred IUPAC name
3-Oxopropanoic acid | |
| Other names
malonic semialdehyde, formylacetic acid, 3-oxopropanoate | |
| Identifiers | |
3D model (JSmol) |
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| 1741700 | |
| ChEBI | |
| ChemSpider | |
| 164397 | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| |
| |
| 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] | |
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| Warning | |
| Flash point | 111.6 °C[2] |
| Related compounds | |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
Natural occurrence
[edit]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
[edit]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
[edit]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
[edit]- ↑ "SAFETY DATA SHEET" (PDF). BLD Pharm. Retrieved 17 June 2025.
- ↑ "3-oxopropanoic acid". chemsrc.com. Retrieved 17 June 2025.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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. hdl:2115/10507. ISSN 1352-2310. Retrieved 17 June 2025.
- 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.
- ↑ 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.