Dihydroxyacetone

Dihydroxyacetone /ˌdaɪhaɪˌdrɒksiˈæsɪtoʊn/ (listen) (DHA), also known as glycerone, is a simple saccharide (a triose) with formula C3H6O3. Dihydroxyacetone /ˌdaɪhaɪˌdrɒksiˈæsɪtoʊn/ (listen) (DHA), also known as glycerone, is a simple saccharide (a triose) with formula C3H6O3. DHA is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, and by the fermentation of glycerin. DHA is a hygroscopic white crystalline powder. It has a sweet cooling taste and a characteristic odor. It is the simplest of all ketoses and has no chiral center or optical activity. The normal form is a dimer (2,5-bis(hydroxymethyl)-1,4-dioxane-2,5-diol) which is slowly soluble in one part water and 15 parts ethanol. When freshly prepared, it reverts rapidly to the monomer in solution. The monomer is very soluble in water, ethanol, diethyl ether and acetone and toluene. DHA may be prepared, along with glyceraldehyde, by the mild oxidation of glycerol, for example with hydrogen peroxide and a ferrous salt as catalyst. It can also be prepared in high yield and selectivity at room temperature from glycerol using cationic palladium-based catalysts with oxygen, air or benzoquinone acting as co-oxidants. Glyceraldehyde is a structural isomer of dihydroxyacetone. Its phosphorylated form, dihydroxyacetone phosphate (DHAP), takes part in glycolysis, and it is an intermediate product of fructose metabolism. DHA was first recognized as a skin coloring agent by German scientists in the 1920s. Through its use in the X-ray process, it was noted as causing the skin surface to turn brown when spilled. In the 1950s, Eva Wittgenstein at the University of Cincinnati did further research with dihydroxyacetone. Her studies involved using DHA as an oral drug for assisting children with glycogen storage disease. The children received large doses of DHA by mouth, and sometimes spat or spilled the substance onto their skin. Healthcare workers noticed that the skin turned brown after a few hours of DHA exposure. Eva Wittgenstein continued to experiment with DHA, painting liquid solutions of it onto her own skin. She was able to consistently reproduce the pigmentation effect, and noted that DHA did not appear to penetrate beyond the stratum corneum, or dead skin surface layer (the FDA eventually concluded this is not entirely true). Research then continued on DHA's skin coloring effect in relation to treatment for patients suffering from vitiligo.