Preparation, binding behaviours and thermal stability of inclusion complexes between (Z)-jasmone and acyclic cucurbit[n]urils

Abstract

(Z)-jasmone is the most important contribution to the scents of perfumes and cosmetics. However, (Z)-jasmone is water insoluble and highly volatile, which limits its development and application. Inclusion technology has become a promising strategy to improve the solubility and stability of hydrophobic small molecules. Here, we used saturated aqueous solution and freeze-drying method to prepare solid inclusion complexes of (Z)-jasmone and three acyclic cucurbit[n]urils (ACBs, M1-M3), and studied their binding behaviours by fluorescence spectroscopy, NMR, XRD, FT-IR, TG and DSC, confirming the formation of the host-guest inclusion complexes. The stoichiometry of inclusion complexes was 1:1 by Job's plot. The inclusion complexes exhibited better water solubility, higher thermal stability and heat-controlled release comparing with that of native (Z)-jasmone. This work uncloses a new strategy to enhance the performance of essential oil and flavours/fragrances and further application in the field of cosmetic and food industry.