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Names | |
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Preferred IUPAC name
1-Aminopropan-2-one
[1] | |
Other names
Aminoacetone
[1]
alpha-Aminoacetone | |
Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.236.907 |
KEGG | |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C3H7NO | |
Molar mass | 73.095 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Aminoacetone is the organic compound with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms isolable salts, e.g. aminoacetone hydrochloride ([CH3C(O)CH2NH3]Cl)). The semicarbazone of the hydrochloride is another bench-stable precursor. [2] Aminoacetone is a metabolite that is implicated in the biosynthesis of methylglyoxal. [3]
Aminoacetone is also produced during catabolism of the amino acid threonine. Threonine is first dehydrogenated to 2-amino-3-oxobutyrate, which is unstable and spontaneously decarboxylates to aminoacetone. Aminoacetone is then oxidized and deaminated, giving 2-oxopropanal (methylglyoxal), which is in turn oxidized to pyruvate. This pathway is the most important catabolic pathway of threonine in mammals. [4]