Environmentally Friendly Sunscreens: Mechanochemical Synthesis and Characterization of β-CD Inclusion Complexes of Avobenzone and Octinoxate with Improved Photostability

Abstract

We report on the mechanochemical synthesis of inclusion complexes obtained by reacting β-cyclodextrin (β-CD) with two widely used sunscreens, namely, avobenzone (AVO) and octinoxate (OCT). Formation of crystalline inclusion complexes was confirmed via a combination of solid-state techniques, including X-ray diffraction (XRD), Raman, and ATR-FTIR spectroscopies. A new, metastable polymorph of avobenzone was also isolated and characterized. NMR spectroscopy and thermal analyses (TGA and DSC) allowed us to evaluate the host/guest ratio and the water content (ca. 8H2O) in crystalline (β-CD)2·AVO and (β-CD)3·OCT2. Photodegradation of the two sunscreens upon inclusion in the hydrophobic cavity of β-CD was evaluated in solution via mass spectrometry (ESI-MS) and UV-vis spectroscopy and found to be sharply reduced. All findings indicate that the inclusion of AVO and OCT in β-CD might represent a viable route for the preparation of environmentally friendly sunscreens with improved photostability to be used in formulations of sun creams.