Composition, enantiomeric distribution, and antibacterial activity of the essential oil of Achillea ligustica All. from Corsica

The essential oil of Achillea ligustica from Corsica was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 82 compounds representing 94.0% of the oil were tentatively identified. The main constituents were the camphane derivatives, representing >30% (camphor, 21.3%; borneol, 6.2%; bornyl acetate, 3.5%) of the whole oil, and santolina alcohol (19.3%). The enantiomeric distribution of 8 chiral constituents was determined by GC-MS using two enantioselective stationary phases (DIME-beta-CD and Lipodex-E). Racemic santolina alcohol, required for optimization of the enantioselective GC conditions, was prepared by an original two-step synthesis from 2,5-dimethylhexa-2,4-diene. The whole essential oil was tested for its antibacterial activity against a wide range of bacteria using a paper disk method. The results show a promising activity against Streptomyces species.     

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.