Hydroxyacetone

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Hydroxyacetone
Acetols.svg
Names
Preferred IUPAC name
1-Hydroxypropan-2-one
Other names
1-Hydroxy-2-propanone
Acetol
Identifiers
3D model (JSmol)
605368
ChemSpider
ECHA InfoCard 100.003.750
EC Number 204-124-8
Properties
C3H6O2
Molar mass 74.08
Appearance Colourless liquid
Odor sweet
Density 1.059 g/cm3[1]
Melting point −17 °C (1 °F; 256 K)
Boiling point 145–146 °C (293–295 °F; 418–419 K)
Vapor pressure 7.5 hPa at 20 °C[2]
1.415[1]
Hazards
H226[2]
Flash point 56 °C (closed cup)[2]
Explosive limits Upper limit: 14.9%(V)
Lower limit: 3%(V)[2]
Lethal dose or concentration (LD, LC):
2200 mg/kg (rat, oral)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hydroxyacetone, also known as acetol, is an organic chemical consisting of a primary alcohol substituent on acetone. It is an α-hydroxyketone, also called a ketol, and is the simplest hydroxy ketone structure.

Hydryoxyacetone can be produced by degradation of various sugars; in foods, it is formed by the Maillard reaction, and can react further to form other compounds with various aromas.[4] As such it finds some use as a flavoring.

Hydroxyacetone is commercially available but may be also be synthesized on a laboratory scale by a substitution reaction on bromoacetone,[5] it undergoes rapid polymerization, including forming a hemiacetal cyclic dimer. Under alkaline conditions, it undergoes a rapid aldol condensation.

See also[edit]

  • Acyloin, the simplest secondary α-hydroxy ketone.

References[edit]

  1. ^ a b Nodzu, Ryuzaburo (1935). "On the Action of Phosphate Upon Hexoses. I. The Formation of Acetol From Glucose in Acidic Solution of Potassium Phosphate". Bul. Chem. Soc. Jpn. 10 (3): 122–130. doi:10.1246/bcsj.10.122. 
  2. ^ a b c d Sigma-Aldrich Co., Hydroxyacetone. Retrieved on 2 July 2015.
  3. ^ Smyth, H. F., Jr; Carpenter, C. P. (January 1948). "Further experience with the range finding test in the industrial toxicology laboratory". The Journal of industrial hygiene and toxicology. 30 (1): 63–8. PMID 18895731. 
  4. ^ Nursten, Harry E. (1998). "The Mechanism of Formation of 3-Methylcyclopent-2-en-2-olone". In O'Brien, J.; Nursten, H. E.; Crabbe, M. J.; Ames, J. M. The Maillard Reaction in Foods and Medicine. Elsevier. pp. 65–68. ISBN 9781845698447. 
  5. ^ Levene, P. A.; Walti, A. (1930). "Acetol". Org. Synth. 10: 1. ; Coll. Vol., 2, p. 5