Environmentally Friendly Sunscreens: Mechanochemical Synthesis and Characterization of β-CD Inclusion Complexes of Avobenzone and Octinoxate with Improved Photostability
Simone D’Agostino, Alessandra Azzali, Lucia Casali, Paola Taddei, Fabrizia Grepioni
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.