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Aminoacetone

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(Redirected from 3-aminoacetone)
Aminoacetone
Names
Preferred IUPAC name 1-Aminopropan-2-one
Other names Aminoacetone
alpha-Aminoacetone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.236.907 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H7NO/c1-3(5)2-4/h2,4H2,1H3Key: BCDGQXUMWHRQCB-UHFFFAOYSA-N
  • InChI=1/C3H7NO/c1-3(5)2-4/h2,4H2,1H3Key: BCDGQXUMWHRQCB-UHFFFAOYAB
SMILES
  • O=C(C)CN
Properties
Chemical formula C3H7NO
Molar mass 73.095 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) 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 (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. ^ 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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