Hydroxyacetone

Hydroxyacetone, also known as acetol, is the organic chemical with the formula CH₃C(O)CH₂OH. It consists of a primary alcohol substituent on acetone. It is an α-hydroxyketone, also called a ketol, and is the simplest hydroxy ketone structure. It is a colorless, distillable liquid.

Hydroxyacetone

Names
Preferred IUPAC name 1-Hydroxyacetone
Systematic IUPAC name 1-Hydroxypropan-2-one
Other names 1-Hydroxy-2-propanone Acetomethyl alcohol 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
PubChem CID	8299
UNII	7I7YM0835W
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	74.079 g·mol−1
Appearance	Colorless 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]
Refractive index (nD)	1.415[1]
Hazards
GHS labelling:
Hazard statements	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):
LD50 (median dose)	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

Preparation

It is produced commercially by dehydration of glycerol.^[4]

Hydroxyacetone is commercially available, but it also may be synthesized on a laboratory scale by a substitution reaction on bromoacetone.^[5]

Reactions

It undergoes rapid polymerization, including forming a hemiacetal cyclic dimer. Under alkaline conditions, it undergoes a rapid aldol condensation.

Hydroxyacetone can be produced by degradation of various sugars. In foods, it is formed by the Maillard reaction. It reacts further to form other compounds with various aromas.^[6] As such it finds some use as a flavoring.

See also

• Acyloin, the simplest secondary α-hydroxy ketone.