Combinatorial synthesis by nature: volatile organic sulfur-containing constituents of Ruta chalepensis L.
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.
Escher
Sina
S
Firmenich SA, Corporate R&D Division, P.O. Box 239, CH-1211 Geneva 8.
Niclass
Yvan
Y
van de Waal
Matthijs
M
Starkenmann
Christian
C
D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010476:Perfume / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D035261:Plant Components, Aerial / Q000737:chemistry; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D032105:Ruta / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D014835:Volatilization
D010476:Perfume; D010936:Plant Extracts; D013457:Sulfur Compounds