Hydroxyacetone Explained

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.

Preparation

It is produced commercially by dehydration of glycerol.

Hydroxyacetone is commercially available, but it also may be synthesized on a laboratory scale by a substitution reaction on bromoacetone.[1]

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.[2] As such it finds some use as a flavoring.

See also

Notes and References

  1. Org. Synth.. Levene. P. A.. Walti. A. . Acetol . 1930 . 10 . 1. 10.15227/orgsyn.010.0001.
  2. Book: The Maillard Reaction in Foods and Medicine . J. . O'Brien . H. E. . Nursten . M. J. . Crabbe . J. M. . Ames . Elsevier . 1998 . 9781845698447 . The Mechanism of Formation of 3-Methylcyclopent-2-en-2-olone . Harry E. . Nursten . 65–68 .