| Title: | Combinatorial synthesis by nature: volatile organic sulfur-containing constituents of Ruta chalepensis L |
| Author(s): | Escher S; Niclass Y; van de Waal M; Starkenmann C; |
| Address: | "Firmenich SA, Corporate R&D Division, P.O. Box 239, CH-1211 Geneva 8" |
| ISSN/ISBN: | 1612-1880 (Electronic) 1612-1872 (Linking) |
| Abstract: | "Ongoing interest in discovering new natural fragrance and flavor ingredients prompted us to examine a solvent extract of sulfurous-sweaty smelling Ruta chalepensis L. (Rutaceae) plant material more closely. Twenty-one sulfur-containing constituents of similar structures were identified by GC/MS techniques. Amongst them, 14 have never been described to occur in nature. The compounds 1-18 belong to a family of natural flavor and fragrance molecules having a 1,3-positioned O,S moiety in common. The identities of the natural constituents were confirmed by comparison with synthetic reference samples, and the organoleptic properties of the latter were studied. The relative and absolute configurations of the four stereoisomers of 4-methyl-3-sulfanylhexan-1-ol (5) were established by stereoselective synthesis. The natural isomers consisted of a 65 : 35 mixture of (3R,4S)-5 and (3S,4S)-5" |
| Keywords: | "Gas Chromatography-Mass Spectrometry Magnetic Resonance Spectroscopy Molecular Structure *Perfume/chemical synthesis/chemistry/isolation & purification Plant Components, Aerial/chemistry Plant Extracts/chemical synthesis/chemistry/isolation & purification;" |
| Notes: | "MedlineEscher, Sina Niclass, Yvan van de Waal, Matthijs Starkenmann, Christian eng Switzerland 2006/12/29 Chem Biodivers. 2006 Sep; 3(9):943-57. doi: 10.1002/cbdv.200690103" |
