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aminoacetone
Sign in to saveAlso known as Amino-2-propanone, Amino-(6CI)-2-propanone, alpha-Aminoacetone, 1-Amino-(8CI,9CI)-2-propanone, 1-aminopropanone, aminopropanone, 1-amino-2-propanone, 1-aminopropan-2-one
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. Aminoacetone is a metabolite that is implicated in the biosynthesis of methylglyoxal.
Chemical data
- Formula
- C3H7NO
- Molecular weight
- 73.09 g/mol
- IUPAC name
- 1-aminopropan-2-one
- SMILES
- CC(=O)CN
- InChIKey
- BCDGQXUMWHRQCB-UHFFFAOYSA-N
- XLogP
- -1
- Polar surface area
- 43.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- ketone
- Mass
- 73.053
Show 4 more facts
- chemical formula
- C₃H₇NO
- canonical SMILES
- CC(=O)CN
- found in taxon
- Escherichia coli
- subject has role
- primary metabolite
via Wikidata · CC0
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Encyclopedic overview
2 sectionsContents
- See also
- References
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. Aminoacetone is a metabolite that is implicated in the biosynthesis of methylglyoxal.
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.
Excerpted from Wikipedia’s “aminoacetone” article, available under the CC BY-SA 4.0 licence.