Thermodynamics and quantum mechanical insights into benzoic acid-acetate ester interactions for aroma modulation and...

This study investigated molecular interactions between benzoic acids (gallic acid/protocatechuic acid) and acetate esters using thermodynamics and quantum mechanics, as well as the effects of benzoic acids on acetate esters release and perception in simplified and real wine systems, respectively. Results showed spontaneous binding (ΔG < 0) between benzoic acids and acetate esters (ethyl octanoate > ethyl hexanoate > isoamyl acetate > ethyl butyrate > ethyl acetate), with gallic acid exhibiting stronger affinities. The -OH of benzoic acids and -COO- of acetate esters were the key groups, driven synergistically by hydrogen bonding, dispersion interactions, and hydrophobic effects, while electrostatic contributions dominated interaction energies (43-60 %). Benzoic acids significantly reduced acetate esters release, showing structure- and concentration-dependent trends. Aroma profile and perception revealed benzoic acids promoted formation and retention of fermentation aroma, enhancing flavor and fruitiness. These findings provided mechanistic insights for modulating wine aroma through benzoic acid- acetate ester interactions.