Aminoacetone
Chemical compound / From Wikipedia, the free encyclopedia
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]
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Preferred IUPAC name
1-Aminopropan-2-one[1] | |
Other names
Aminoacetone[1] alpha-Aminoacetone | |
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3D model (JSmol) |
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ChEBI | |
ChemSpider |
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ECHA InfoCard | 100.236.907 |
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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 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]