Mercaptoalcohols and mercaptoketones are examples of polyfunctional thiols, a class of compounds known as outstanding contributors to the flavor of many foods. They are characterized by low odor thresholds and pronounced odor properties. Recent studies demonstrated the importance of the stereochemistry for the sensory properties of 4-mercapto-2-alkanones.This presentation focuses on the corresponding 4-mercapto-2-alkanols: (i) The stereoisomers of a homologous series of 4-mercapto-2-alkanols were separated via capillary gas chromatography (GC) using chiral stationary phases. (ii) Absolute configurations were assigned via NMR analysis in combination with lipase-catalyzed kinetic resolutions. (iii) Odor properties and odor thresholds of the stereoisomers were determined via GC-olfactometry. (iv) Polyfunctional thiols were isolated from natural sources and the naturally occurring distributions of the stereoisomers were determined using multidimensional GC.

Stereoisomers of 4-mercapto-2-alkanols: Analysis, sensory evaluations, and natural occurrence

248th National Meeting (2014)

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