(-)-Menthol-β-cyclodextrin inclusion complex production and characterization

Abstract

(-)-Menthol has been widely used in clinical medicine, flavor, and fragrance. However, high volatility, short retention time, low solubility in water, and whisker growth of menthol are crucial problems for its application. In this paper, (-)-menthol-β-cyclodextrin inclusion complex was fabricated to solve these problems. The product was characterized by X-ray diffraction, Fourier transform infrared spectroscopy and thermogravimetric analysis. The results showed that menthol was successfully encapsulated in the cavity of β-cyclodextrin. Menthol itself vaporized almost completely at around 120 oC, while the maximum menthol release rate occurred at 267.5 oC after the formation of the inclusion complex. The stability and retention time were improved. The menthol release reaction order, apparent activation energy and the pre-exponential factor were obtained and their values were 0, 142.9 kJ/mol and 1.6 × 1013 respectively. The structure of menthol-β-cyclodextrin inclusion complex was investigated by molecular simulation and the minimum energy, –116.7 kJ/mol, was obtained at –0.8 × 10–10 m.

Keywords

• menthol-β-cyclodextrin inclusion complex
• preparation
• characterization
• kinetics
• molecular mechanics