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". Organic Syntheses. 10: 1. ; Collective Volume, 2, p. 5