Aminoacetone

Aminoacetone is the simplest monopeptide with the formula CH3C(O)CH2NH2. Although stable in the gaseous form, once condensed it reacts with itself. The protonated derivative forms stable 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
Names
Preferred IUPAC name
1-Aminopropan-2-one[1]
Other names
Aminoacetone[1]
alpha-Aminoacetone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.236.907
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).
☒N verify (what is checkY☒N ?)
Infobox references

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.


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