Aminoacetone

Aminoacetone
Names
	Preferred IUPAC name 1-Aminopropan-2-one
	Other names Aminoacetone; alpha-Aminoacetone
Identifiers
CAS Number	298-08-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17906 ;
ChemSpider	210 ;
ECHA InfoCard	100.236.907
KEGG	C01888 ;
PubChem CID	215;
UNII	ZB4ES38S4R ;
CompTox Dashboard (EPA)	DTXSID10183939 ;
	InChI InChI=1S/C3H7NO/c1-3(5)2-4/h2,4H2,1H3 Key: BCDGQXUMWHRQCB-UHFFFAOYSA-N ; InChI=1/C3H7NO/c1-3(5)2-4/h2,4H2,1H3 Key: BCDGQXUMWHRQCB-UHFFFAOYAB;
	SMILES 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). verify (what is ?) Infobox 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.^[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]

References

^ ^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.
^ John D. Hepworth (1965). "Aminoacetone Semicarbazone Hydrochloride". Organic Syntheses. 45: 1. doi:10.15227/orgsyn.045.0001.
^ 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.
^ 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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[iupac2013-1] 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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See also

References