Solution Chemistry of Dihydroxyacetone and Synthesis of Monomeric Dihydroxyacetone.

ABSTRACT: Dihydroxyacetone (DHA) is a major byproduct of e-cigarette combustion and is the active ingredient in sunless tanning products. Mounting evidence points to its damaging effects on cellular functions. While developing a simple synthetic route to monomeric [¹³C₃]DHA for flux metabolic studies that compared DHA and glyceraldehyde (GA) metabolism, we uncovered that solid DHA ages upon storage and differences in the relative abundance of each of its isomer occur when reconstituted in an aqueous solution. While all three of the dimeric forms of DHA ultimately resolve to the ketone and hydrated forms of monomeric DHA once in water at room temperature, these species require hours rather than minutes to reach an equilibrium favoring the monomeric species. Consequently, when us

SUBMITTER: Belfleur L 

PROVIDER: S-EPMC9020455 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature