Aminoacetone

Aminoacetone
Names
Preferred IUPAC name
1-Aminopropan-2-one[1]
Other names
Aminoacetone[1]
alpha-Aminoacetone
Identifiers
CAS Number
  • 298-08-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17906 checkY
ChemSpider
  • 210 checkY
ECHA InfoCard 100.236.907 Edit this at Wikidata
KEGG
  • C01888 checkY
PubChem CID
  • 215
UNII
  • ZB4ES38S4R checkY
CompTox Dashboard (EPA)
  • DTXSID10183939 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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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Infobox references
Chemical compound

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]

See also

References

  1. ^ a b 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.


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