Abstract
The increasing concern about the environmental impact of ingredients largely used as sunscreens today is pushing research towards new frontiers for the synthesis and degradation potential of innovative sun protection structures. This study deals with the design, synthesis, efficacy evaluation, and environmental impact of new photo-stable molecules at extended electronic conjugation and which have the ‘charge-transfer’ type of optical transition (push and pull). They efficiently perform absorption of electro-magnetic radiation in the UVB and UVA regions. A preliminary screening, dealing with a whole series of aromatic donors, led to the selection of a key substrate derived from waste material, provided with low environmental impact and largely available on the market. As far as the acceptor was concerned, an ester with cyan-acrylic structure and functionalized with aliphatic chains emerged as the most suitable. This allowed a shift of the λ of absorption in the range of the ultraviolet wavelengths. The synthesis procedures include an acid-catalyst-fitted esterification, condensation, and cold crystallization. It was continuously monitored with suitable characterization instruments (GC-MS, 1H NMR, 13C NMR), in order to avoid by-products and parasitic reactions. The resulting structures (patent pending) are composed by a furan core condensed with cyano-acrylic esters, derivatized with branched chains of hydrocarbons of medium length. The obtained structures are capable of good absorption in the range of wavelengths between 300 and 400 nm. Because of their structures, the new molecules are largely soluble in many common oils and cosmetic ingredients. The new molecules have been successively evaluated in terms of photo-stability, biodegradability, compatibility, and UVB-UVA protection capability, both in-vivo and in-vitro, in comparison with existing sunscreens.
Highlights
The tools of synthetic chemistry play a key role in the field of cosmetics
Elmer lambda 35 (PerkinElmer, Inc., Waltham, MA, USA), the sun protection factor (SPF) in vivo test was recorded on a Multiport Solar UV Simulator Model 601-300 watts (Solar Light Company, Inc., Glenside, PA 19038, USA), and the UVA in vitro efficacy was measured by a Labsphere UV-2000S
Starting from the left of the HNMR spectrum, the aromatic hydrogens in the region all peaks were integrated and characterized in order to understand if the recorded molecule coincided with our target
Summary
The tools of synthetic chemistry play a key role in the field of cosmetics. The possibility of manipulating or synthesizing new raw materials has long fascinated a still growing number of scientists, who are constantly searching for new compounds. The chemical synthesis of cosmetic raw materials, in general, is considered necessary when problems arise, for example, related to structural factors, or efficacy or compatibility with the formulation. Embedding of multiple functions within a single structure could be beneficial for the cosmetics field [1]. Sustainability, renewability, and low environmental impact are playing an increasingly relevant role in pushing scientific frontiers, following both legislative requirements and ethical guidelines [2]. Among the innovative synthetic compounds of interest in the cosmetic industry, UV filters are relevant
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