Hydroxyacetone, also known as acetol, is the
organic chemical
Some chemical authorities define an organic compound as a chemical compound that contains a Carbon–hydrogen bond, carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. F ...
with the formula CH
3C(O)CH
2OH. It consists of a
primary alcohol
A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group.
In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary ...
substituent on
acetone
Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
. It is an
α-hydroxyketone, also called a ketol, and is the simplest
hydroxy ketone
In organic chemistry, a hydroxy ketone (often referred to simply as a ketol) is a functional group consisting of a ketone () flanked by a hydroxyl group (). Chemicals in this group can be classified by the position of the hydroxyl relative to the ...
structure. It is a colorless, distillable liquid.
Preparation
It is produced commercially by dehydration of
glycerol
Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...
.
Hydroxyacetone is commercially available, but it also may be synthesized on a laboratory scale by a
substitution reaction
A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions ar ...
on
bromoacetone
Bromoacetone is an organic compound with the formula . It is a colorless liquid although impure samples appear yellow or even brown. It is a lachrymatory agent and a precursor to other organic compounds.
Occurrence in nature
Bromoacetone is pr ...
.
Reactions
It undergoes rapid
polymerization
In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...
, including forming a
hemiacetal
In organic chemistry, a hemiacetal is a functional group the general formula , where is a hydrogen atom or an organic substituent. They generally result from the nucleophilic Addition reaction, addition of an Alcohol (chemistry), alcohol (a compo ...
cyclic
dimer
Dimer may refer to:
* Dimer (chemistry), a chemical structure formed from two similar sub-units
** Protein dimer, a protein quaternary structure
** d-dimer
** TH-dimer
* Dimer model, an item in statistical mechanics, based on ''domino tiling''
* ...
. Under
alkaline
In chemistry, an alkali (; from the Arabic word , ) is a basic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a soluble base has a pH greater than 7.0. The ...
conditions, it undergoes a rapid
aldol condensation
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...
.
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.
As such it finds some use as a flavoring.
See also
*
Acyloin
In organic chemistry, acyloins or α-hydroxy ketones are a class of organic compounds of the general form , composed of a hydroxy group () adjacent to a ketone group (). The name ''acyloin'' is derived from the fact that they are formally deri ...
, the simplest secondary α-hydroxy ketone.
References
External links
*{{Commonscatinline
Alpha-hydroxy ketones