Painting and Memory in the Discovery of Aroma Chemicals: The Case of Sulfur Containing Odorants and Odorant Precursors in Axillary Sweat Odor

摘要

The reminiscent human sweat-like odour of Sclarimol~? (3-mercapto-1-methoxyhexane) and Aruscol~? (3-mercapto-1-methoxyheptane), discovered in Salvia sclarea L. and Ruta chalepensis L., prompted us to look for sulfur compounds in human axillary sweat. This analytical work led us to the discovery of Transpirol? ((R/S)-3-mercapto-3-methyl-l-hexanol), and to the development of a new technology: the MDGC-DCSI. This new invention allowed us to determine the enantiomer ratio of sulfur compounds in the natural extract. The same principle can be applied to GC-Olfaction (MDGC-DCSI-Ofactometry), in order to increase the difference in retention time between enantiomers eluted through the sniffing port. Finally this work addressed the question of which compound is the precursor of the Transpirol? and after multiple liquid chromatography separations, [1-(2-hydroxyethyl)-1 -methylbutyl]-L-cysteinylglycine (Cys-Gly-(S)-conjugate), was formally identified as the precursor excreted by axillary glands.