3-Oxopropanoic acid
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| 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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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]