Inclusion complexes of cyclomaltoheptaose (β-cyclodextrin) and its methylated derivatives with the main components of the pheromone of the olive fruit fly

Abstract The inclusion complexes of cyclomaltoheptaose (βCD) and heptakis(2,3,6-tri- O -methyl)cyclomaltoheptaose (TM-βCD) with the four major components of the pheromone of the olive fruit fly ( Dacus oleae ), namely 1,7-dioxaspiro[5.5]undecane, (−)-α-pinene, nonanal, and ethyl dodecanoate, and the complex of heptakis(2,6-di- O -methyl)cyclomaltoheptaose (DM-βCD) with 1,7-dioxaspiro[5.5]undecane were studied. The complexes were characterised in the solid state by differential scanning calorimetry and X-ray powder diffraction. In aqueous solution, the structure of the complexes was investigated by 1 H NMR spectroscopy. In solution, 1,7-dioxaspiro[5.5]undecane, (−)-α-pinene, and nonanal enter the cavity of the cyclo-oligosaccharides. Association constants for some of these complexes were also measured. The complexes of ethyl dodecanoate did not provide evidence of their structure in solution. This was attributed to the existence of negligible amounts of these complexes in water due to the combined effects of low solubility and low association constant.