Identification of new, odor-active thiocarbamates in cress extracts and structure-activity studies on synthesized homologues.
New, odorant nitrogen- and sulfur-containing compounds are identified in cress extracts. Cress belongs to the botanical order Brassicales and produces glucosinolates, which are important precursors of nitrogen- and sulfur-containing compounds. Those compounds often present low perception thresholds and various olfactive notes and are thus of interest to the flavor and fragrance chemistry. When the study of organonitrogen and organosulfur compounds is undertaken, Brassicale extracts are one of the matrices of choice. Cress extracts were studied by analytical (GC-MS, GC-FPD) and chemical (fractionation) means to identify new interesting odorant compounds. Two compounds that have never been reported in cress extracts, containing both nitrogen and sulfur, were discovered: N-benzyl O-ethyl thiocarbamate and N-phenethyl O-ethyl thiocarbamate. These two molecules being of organoleptic interest, their homologues were synthesized and submitted to organoleptic tests (static and GC-sniffing). Their odors evolve from garlic and onion over green, mushroom- and cress-like to fresh, spearmint-like. This paper presents the origin, chemical synthesis, and organoleptic properties of a series of O-alkyl thiocarbamates.
Breme
Katharina
K
LCMBA, UMR CNRS 6001, Université de Nice-Sophia Antipolis, Parc Valrose, F-06108 Nice Cedex 2, France.
Fernandez
Xavier
X
Meierhenrich
Uwe J
UJ
Brevard
Hugues
H
Joulain
Daniel
D
D019607:Brassicaceae / Q000737:chemistry*; D002849:Chromatography, Gas; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D009584:Nitrogen / Q000032:analysis; D009812:Odorants / Q000032:analysis*; D010936:Plant Extracts / Q000737:chemistry*; D012903:Smell; D013329:Structure-Activity Relationship; D013455:Sulfur / Q000032:analysis; D013859:Thiocarbamates / Q000032:analysis*
D010936:Plant Extracts; D013859:Thiocarbamates; D013455:Sulfur; D009584:Nitrogen