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Combinatorial Synthesis by Nature: Volatile Organic Sulfur‐Containing Constituents of Ruta chalepensis L.
Author(s) -
Escher Sina,
Niclass Yvan,
van de Waal Matthijs,
Starkenmann Christian
Publication year - 2006
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200690103
Subject(s) - chemistry , organoleptic , flavor , sulfur , moiety , rutaceae , organic chemistry , molecule , stereochemistry , botany , food science , biology
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 (3 R ,4 S )‐ 5 and (3 S ,4 S )‐ 5 .