Due to their extremely low odor thresholds, thiols often show a major impact on the overall aroma of foods, even if present in trace amounts. Thereby, odor qualities as well as odor thresholds of thiols are often influenced by chirality. For example, some stereoisomers of 3-mercapto-2-methylpentan-1-ol are among the most potent food odorants, whereas others show only weak odors. In order to gain a deeper insight into structure-odor correlations, different series of chiral mercapto-containing key aroma compounds and their homologues were synthesized, such as 3-mercaptoalkan-1-ols, 2-methyl-3-mercaptoalkan-1-ols, and 1-phenylalkane-1-thiols. Enantiomers were separated and their odor qualities and thresholds were determined. Absolute configurations were elucidated using either enantioselective synthesis or 1H-NMR anisotropy methods. In the lecture, structure-odor correlations are discussed with respect to the influence of chirality on sensory properties of thiols.

Influence of chirality on mercapto-containing key aroma compounds

248th National Meeting (2014)

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