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Dihydroxyacetone: an Updated Insight Into an Important Bioproduct

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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. DHA reacts with the protein keratin on the skin surface, pro- The skin of the children that casually and accidentally came ducing pigmentscalled melanoidins,polymericcompounds into contact with DHA in solution turned brown, whereas tex- that are linked by lysine chains to the proteins of the stratum tiles didnot.[8] Wittgenstein and Berry concluded their 1960 corneum.[4] “artificialtan” study[9] by reporting findings on the mechanism of skin staining with DHA, stating that it “appears to proceed through combination with free amino groups in skin proteins, and particularly by combination of DHA with the free guanido group in arginine”.[9] Fifty five years later (in 2015), driven by consumer demand for afashionable tan throughout the whole year and by con- [10] Scheme1.Dimeric DHA in the solid state dissociates into amixture of free comitantincreasing awareness of UV photodamage hazards, carbonyl and hydrated monomersupondissolution. one of the leading self-tanning product manufacturers sold out ayear’s worth of stock of its in-shower tanning lotion in only one day.[11] Already in 2011, 41%ofwomen in the UK [a] Dr.R.Ciriminna, Dr.M.Pagliaro were reported to use self-tanning products.[12] In this study, Istituto per lo Studio dei MaterialiNanostrutturati, CNR via U. La Malfa 153, 90146 Palermo (Italy) we provide an updated bioeconomyperspective into avalued E-mail:[email protected] bioproduct (DHA), whose supply and productionfrom [b] Dr.A.Fidalgo, Prof. L. M. Ilharco readily available glycerol, we argue, will rapidlyexpand and Centro de Química-Física Molecular and diversify. IN-InstituteofNanoscience and Nanotechnology Instituto Superior TØcnico, UniversidadedeLisboa Av.Rovisco Pais 1, 1049-001 Lisboa (Portugal) 2. Quality and Health Aspects E-mail:[email protected] The ORCID identification number(s) for the author(s) of this article can DHA has been approved across the world for use in self-tan- be found under: ning products for several decades. To quote an industry’s prac- https://doi.org/10.1002/open.201700201. titioner “no other substance, so far,has been capable to pro- 2018 The Authors. Published by Wiley-VCH Verlag GmbH &Co. KGaA. vide more satisfactory or more lasting results”.[6] In the EU, for This is an openaccessarticleunder the termsofthe Creative Commons AttributionLicense, which permits use, distribution and reproduction in example, the Scientific Committee on Consumer Safety evalu- any medium, provided the original work is properly cited. ated the safety of DHA as aself-tanningingredient in cosmetic ChemistryOpen 2018, 7,233 –236 233 2018 The Authors. PublishedbyWiley-VCH Verlag GmbH &Co. KGaA, Weinheim formulations, in 2010, and concluded that the use of DHA in Further improvements originate from purer DHA made avail- skin formulations at concentrationsupto10% will not pose a able by suppliers, preferably in powder form (the degradation risk to the health of the consumer.[13] Several medicalassocia- of DHA in this form is negligible when stored at room temper- tions recommend it as asafer alternative to UV radiationfrom ature for one year;whereas a10% DHA aqueous solution the sun or from hazardoustanning beds (“we don’t callthose stored at 40 8Cfor 6months shows aloss of approximately UV tanning booths;wecall them tanning coffins”).[14] Exposure 25%ofthe active ingredient).[22] to UV radiation and, in particular,toindoor tanning beds can Anon-exhaustive Review[23] of recent progress startedin cause skin cancer, skin burns, and premature skin aging.Cur- 2011, when research chemists at alarge chemical company in- rent misconceptions among the general public about the es- troducedanew formulation, in which DHA wasadded in alow tablished risks of DHA-containingsunless tanning products, as amount (from aconcentration of ca. 0.01%toca. 0.9 %) to a well as guidelines for their proper use,have been reviewed topical cosmetic base comprisingmoisturizers, vitamins, bota- lately.[15] nicals,oils, and sunscreen agents. This was formulated as an Sunless tanning products containing DHA produce, within a emulsion with the aid of an emulsifier suitable for topical use few hours, arelativelylong-lasting tan (from 3to10days, de- on skin, such as cetearyl glucoside, whichstrengthens the lipid pending on the formulation), withoutthe risks of photodam- structure within the skin, establishing abarriertomoisture age. As mentioned above, this reactionislimited to the stra- loss.[23] Other examples of similar commercial formulations in- tum corneum (the outer layer of human skin comprised of clude hyaluronic acid (to keep the skin hydrated), hemp seed dead cells), and in vitro skin absorption studies have found no oil extract containingall 21 amino acids for ahealthyskin, significant systemic absorption of DHA when appliedtopically black tea, and Aloe Vera antioxidantswith soothingproper- to the skin.[16] On the other hand, the Maillard reaction be- ties.[24] Furthermore, some of the DHA added to the formula- tween DHA and amino acids generates reactive oxygen species tion is microencapsulated, so as to provide along-lasting tan (ROS), namely highly reactive free radicals,[17] that may attack through the slow releaseofthe entrapped molecules as well the cell structures and degrade collagen and elastin fibers,pro- as to assurealonger shelf life. moting premature skin aging andwrinkle formation.The pro- Another new formulation consists of tailor-made tanning cess is accelerated under sun radiation,with more than 180% products based on liquid concentrates,blending DHA with additional radicals generatedduring sun exposure with respect raspberryoil and Aloe Vera, which users can combine with to untreated skin, thus requiring short or no sun exposure their moisturizer to create multi-tasking skincare products, when self-tannersare used.[18] It is also relevant here to notice with even sleep-mask tan formulations to replace conventional how,when appliedonthe skin, atypical DHA-based creamat- nightly skincare masks.[25] The list concludes with aself-tanning tenuatesthe sunlight-induced formation of vitamin D.[19] product that includes ablend of EcoCert-certified DHA and er- Owing to the formationofROS, it is perhaps not surprising ythrulose with cardamom seed oil and five aromatic teas, so as that DHA induces DNA damage.[20] More recently,scholars in to avoid the use of any phthalate-containing fragrance to the US confirmed and expandedthese results, showingthat mask the unpleasant smell that often characterizes sunless tan- exposing viable cells to DHA significantly alters the cell micro- ners:natural pigmentsbeet root, blue green algae, caramel, environment, promoting the induction of cell death, in particu- and cocoa powder.[26] lar through internal exposures from inhalation, absorption into In general, the new formulations make the skin appear more mucous membranes, or through broken skin.[21] The team con- moisturized, and the color more naturaland more radiant over cluded that more work is necessary to understand the complex an extended period of time, thereby solving the old orange- metabolic eventsinduced by exposure to DHA. lookingand odor issues typical of former self-tanning composi- Meanwhile, as DHA continuestobeapproved as aself-tan- tions.[23] With today’s advanced formulations, no professional ning ingredient, this is aclear case in which chemical innova- application of sunless tanning products or complex skin prepa- tion aimed at product quality improvement, concomitantly ration steps are required, with products ranging from portable leads to minimized
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