Sensory-Directed Identification of Creaminess-Enhancing Semi-Volatile Lactones in Crumb Chocolate

In order to gain a more comprehensive knowledge of the chemical nature of creaminess-related flavor compounds in milk chocolates on a molecular level, crumb chocolate was analyzed by means of activity guided screening techniques. Sensory studies of a triglyceride-free lipid emulsion indicated that the n-pentane extract showed the highest impact regarding creaminess sensation. Enhancement of creaminess by adding anhydrous milk fat fractions to chocolate was demonstrated by fractionated high-vacuum distillation of different fats associated with the chocolate production combined with sensory experiments. Syntheses of various δ-lactones and the quantification of these sensory active semi-volatiles led to the conclusion that the anhydrous milk fat contains a series of γ- and δ-lactones. Cocoa butter revealed a high concentration of δ-hexadecalactone, too. Experiments suggested that lactones are generated from the potential precursors monohydroxyalkanoic acid(s) esterified (mono-tri)glyceride(s) during heating. Sensory studies exhibited recognition thresholds of 29–40 µmol/kg for the long-chain δ-lactones in crumb chocolate. Furthermore, significant enhancement of the retro-nasal creamy flavor was found for δ-tetradecalactone.