Hydroxyacetone

Hydroxyacetone
Names
	Preferred IUPAC name 1-Hydroxypropan-2-one
	Other names 1-Hydroxy-2-propanone; Acetol
Identifiers
CAS Number	116-09-6;
3D model (JSmol)	Interactive image;
Beilstein Reference	605368
ChemSpider	21106125;
ECHA InfoCard	100.003.750
EC Number	204-124-8;
CompTox Dashboard (EPA)	DTXSID8051590 ;
	InChI InChI=1S/C3H6O2/c1-3(5)2-4/h4H,2H2,1H3 Key: XLSMFKSTNGKWQX-UHFFFAOYSA-N;
	SMILES CC(=O)CO;
Properties
Chemical formula	C3H6O2
Molar mass	74.08
Appearance	Colourless liquid
Odor	sweet
Density	1.059 g/cm3
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
Refractive index (nD)	1.415
Hazards
	GHS labelling:
Hazard statements	H226
Flash point	56 °C (closed cup)
Explosive limits	Upper limit: 14.9%(V); Lower limit: 3%(V)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2200 mg/kg (rat, oral)
	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.

References

^ ^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.
^ ^a ^b ^c ^d Sigma-Aldrich Co., Hydroxyacetone. Retrieved on 2 July 2015.
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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. (eds.). The Maillard Reaction in Foods and Medicine. Elsevier. pp. 65–68. ISBN 9781845698447.
^ Levene, P. A.; Walti, A. (1930). "Acetol". Organic Syntheses. 10: 1; Collected Volumes, vol. 2, p. 5.

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

[JP-1] 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.

[SA-2] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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. (eds.). 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; Collected Volumes, vol. 2, p. 5.

[1]

[2]

[3]

[4]

[5]

See also

References