Dihydroxyacetone

Description

Dihydroxyacetone (DHA) is a ketotriose monosaccharide commonly used as the active ingredient in sunless tanning agents (fake tan). DHA is synonymous with glycerone or 1,3-dihydroxypropan-2-one.

Uses

Dihydroxyacetone (DHA) was originally used as an artificial sweetener for diabetics. In the 1950s, it was also used orally in children with glycogen storage disease and was found to induce brown hyperpigmentation of the skin. DHA is the only FDA-approved sunless tanning agent. It is also used in vitiligo, in order to temporarily induce hyperpigmentation of the affected areas. It is also used in cosmetics as an emulsifier, humectant, plasticiser and biocide.

Preparation

Dihydroxyacetone is a three-carbon sugar that is part of the natural glycolytic pathway. It can be synthesised by fermentation of glycerol by glucose-oxygenated bacteria or by electrocatalytic oxidation.

Definition

ChEBI: Dihydroxyacetone is a ketotriose consisting of acetone bearing hydroxy substituents at positions 1 and 3. The simplest member of the class of ketoses and the parent of the class of glycerones. It has a role as a metabolite, an antifungal agent, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a ketotriose and a primary alpha-hydroxy ketone.

Mechanism of action

Dihydroxyacetone penetrates the stratum corneum when applied topically and undergoes a Maillard reaction (non-enzymatic glycation) with free amino acids such as glycine, alanine, leucine and valine. The product of this reaction is melanoidin, a large pigmented nitrogen-containing structure similar to melanin that darkens the skin.