New Bitter-Masking Compounds: Hydroxylated Benzoic Acid Amides of Aromatic Amines as Structural Analogues of Homoeriodictyol

Starting from the known bitter-masking flavanones eriodictyol and homoeriodictyol from herba santa some structurally related hydroxybenzoic acid amides of benzylamines were synthesized and evaluated as masking agents toward bitterness of caffeine by sensory methods. The closest structural relatives of homoeriodictyol, the hydroxybenzoic acid vanillylamides 5−9, were the most active and were able to reduce the bitterness of a 500 mg L-1 caffeine solution by about 30% at a concentration of 100 mg L-1. 2,4-Dihydroxybenzoic acid vanillylamide 7 showed a clear dose-dependent activity as inhibitor of the bitter taste of caffein between 5 and 500 mg L-1. Additionally, it was possible to reduce the bitterness of quinine and salicine but not of the bitter peptide N-l-leucyl-l-tryptophan. Combinations of homoeriodictyol and amide 7 showed no synergistic or antagonistic changes in activity. The results for model compound 7 suggested that the hitherto unknown masking mechanism is probably the same for flavanones and the new amides. In the future, the new amides may be alternatives for the expensive flavanones to create flavor solutions to mask bitterness of pharmaceuticals or foodstuffs. Keywords: Bitter masking; taste modifiers; hydroxylated benzoic acid amides; homoeriodictyol; structure−activity relationship