Recently we reported that the release profile of cinnamaldehyde from a sugar-free chewing gum was correlated to the release of the sugar alcohol phase or was not in agreement with the log P model. The objective of this study was therefore to investigate mechanisms of cinnamaldehyde release from a sugar-free chewing gum; p-cresol (similar log P value) was also analyzed for comparison. Breath analysis of the chewing gum samples over an 8 min consumption period reported that the maximum concentration of cinnamaldehyde was 2- to 3-fold higher during the initial phase of mastication in comparison to the later phase, whereas the concentration of p-cresol was relatively constant over these two time periods. By contrast the release profile of cinnamaldehyde from a flavored gum base (no sugar alcohol phase) was constant over the 8 min consumption period and similar to the release of cresol from the flavored gum base. On the basis of tandem mass spectrometry, cinnamaldehyde was reported to react with sorbitol and generate hemiacetal reaction products that were not stable under slight alkaline conditions; it was suggested to revert back to free cinnamaldehyde and sugar alcohol in the oral cavity. The increased polarity of these transient cinnamaldehyde-sorbitol hemiacetal reaction products would result in a more rapid release rate of cinnamaldehyde than would be typically predicted based on the affinity of cinnamaldehyde for the gum base.