A heat-controlled release system of ethyl vanillin based on acyclic cucurbit[n]urils

Ethyl vanillin (EVA) is one of the most popular spices in the world, but it is unstable and is prone to lose its aroma. Host-Guest encapsulation by supramolecular hosts can improve stability of fragrance molecules and endow them with excellent heat-controlled release properties to satisfy requirements in food, cosmetic and tobacco, etc. Herein, two acyclic cucurbit[n]urils (ACBs, M1 and M2) inclusion complexes of EVA were prepared. Their binding behaviors were investigated by H-1 NMR, SEM, XRD, FT-IR and TGA. The stoichiometric ratio was 1:1 by Job's plot and the binding constant was determined by fluorescence titration. The intermolecular interaction between host and guest was studied by 2D-ROESY NMR and the inclusion mode was proposed. Finally, the heat-controlled release experiment indicated that the inclusion complexes of ACBs/EVA possess less volatilization at higher temperature, longer retention time and heat-controlled release. This study provides theoretical and technical guidance for expanding the application of EVA.