Cyclodextrin, an efficient tool for trans-anethole encapsulation: Chromatographic, spectroscopic, thermal and structural studies

Inclusion complexes of trans-anethole (AN) with alpha-cyclodextrin (alpha-CD), beta-cyclodextrin (beta-cD), hydroxypropyl-beta-cyclodextrin (HP-beta-CD), randomly methylated-beta-cyclodextrin (RAMEB) and a low methylated-beta-cyclodextrin (CRYSMEB) were investigated in aqueous solution by static headspace gas chromatography (SH-GC), phase solubility study, UV-Visible, H-1 NMR and (2D) ROESY NMR spectroscopies. The obtained results indicated the formation of 1:1 inclusion complex for all the studied CDs. Water solubility of AN was significantly improved upon complexation with CDs as demonstrated by phase solubility and retention studies. Solid inclusion complexes were prepared by the freeze-drying method and the encapsulation of AN was confirmed by Fourier transform infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC) studies. Moreover, the degradation of AN, induced by UVC irradiation, was markedly reduced by the formation of CD inclusion complexes. Results showed that encapsulation in CDs was an efficient way to increase solubility and stability of AN, thereby making it valuable for food or pharmaceutical applications. (C) 2014 Elsevier Ltd. All rights reserved.