Sweet–bitter interactions and the solution properties of chlorinated sugars

Among chlorinated sugars, some are intensely sweet, some are bitter and others are tasteless. Although chlorination of sugars provokes an increase in lipophilicity, a certain hydrophilic/lipophilic balance is needed for sweeteners to be perceived. Two chlorinated sugars, sucralose (trichlorogalactosucrose) and methyldichlorogalactoside, respectively known for their enhanced sweetness (650×) and inhibitory effect on the sweetness of sucrose, are studied. Their sapid properties are interpreted on the basis of their physicochemical properties (intrinsic viscosity, apparent specific volume, surface tension, contact angle and vibrational spectra). It is particularly shown that the perturbation of the structure of water by these molecules, compared with that by simple sugars, helps in understanding their taste mechanism.