Aminoacetone

Aminoacetone
Names
Preferred IUPAC name
1-Aminopropan-2-one
Other names
Aminoacetone
alpha-Aminoacetone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.236.907 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H7NO/c1-3(5)2-4/h2,4H2,1H3 checkY
    Key: BCDGQXUMWHRQCB-UHFFFAOYSA-N checkY
  • InChI=1/C3H7NO/c1-3(5)2-4/h2,4H2,1H3
    Key: BCDGQXUMWHRQCB-UHFFFAOYAB
  • O=C(C)CN
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. 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.

See also

References

  1. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 63. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ↑ John D. Hepworth (1965). "Aminoacetone Semicarbazone Hydrochloride". Organic Syntheses. 45: 1. doi:10.15227/orgsyn.045.0001.
  3. ↑ Bechara, Etelvino J.H.; Dutra, Fernando; Cardoso, Vanessa E.S.; Sartori, Adriano; Olympio, Kelly P.K.; Penatti, Carlos A.A.; Adhikari, Avishek; Assunção, Nilson A. (2007). "The dual face of endogenous α-aminoketones: Pro-oxidizing metabolic weapons". Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology. 146 (1–2): 88–110. doi:10.1016/j.cbpc.2006.07.004. PMID 16920403.
  4. ↑ Dobrota, Dušan (2016). Lekárska biochémia [Medical biochemistry] (in Slovak) (2nd ed.). Martin: Osveta. pp. 316–317. ISBN 978-80-8063-444-5.