Dihydroxyacetone: an Updated Insight Into an Important Bioproduct
DOI:10.1002/open.201700201 Dihydroxyacetone:AnUpdated Insight into an Important Bioproduct Rosaria Ciriminna,[a] Alexandra Fidalgo,[b] Laura M. Ilharco,*[b] and Mario Pagliaro*[a] Currently obtained from glycerol through microbial fermenta- to the sun.Weprovideanupdated bioeconomy perspective tion, the demand of 1,3-dihydroxyacetone (DHA)has signifi- into avalued bioproduct (DHA), whose supply and production cantly grown during the course of the last decade, driven by from glycerol, we argue in this study,will rapidly expand and the consumer passion for atan and increasing awareness of diversify,with importantglobal health benefits. UV photodamage to the skin caused by prolonged exposure 1. Introduction Commercially obtained from glycerol through microbial fer- Its browning effects, exploited also to mask the effects of vi- mentation,over the acetic acid bacteria, 1,3-dihydroxyacetone tiligo (treatment with a6%DHA cream,leadingto90% satis- (DHA;1,3-dihydroxy-2-propanone) is the simplest ketone form factionofvitiligo patients),[5] were discovered by accident in of sugars(ketoses) and an important intermediate in carbohy- the 1930s:attempts to treat diabetes patients with oral doses drate metabolism in higherplants and animalsformed during of DHA resultedinadeep yellow coloring of gums.[6] The first glycolysis.[1] In the solid-state, DHA exists as adimer with a self-tanning lotion is said to have been commercialized in 1945 dioxan structure, which, upon dissolution,readily dissociates in California,[6] thoughmost reports agree that sunless tanning into amixture of free carbonyl and hydrated monomers products debuted on the US cosmetic market in 1959.[7] (Scheme 1).[2] In any case, in the 1950s, Wittgenstein rediscovered the skin In atypical Maillardreaction (the reaction of sugars with browning caused by DHA while studying the effect of large amino acids, ubiquitous in cookingand, thus, in dailylife),[3] oral doses of DHA in children with glycogen storage disease.
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