Synthesis, structure elucidation, and olfactometric analysis of lilac aldehyde and lilac alcohol stereoisomers.
Structure elucidation of the lilac aldehyde and lilac alcohol stereoisomers was ascertained by (1)H nuclear magnetic resonance (NMR) spectroscopy, including intramolecular nuclear Overhauser effects of the separated diastereoisomers and anisotropic effects of the diastereomeric 2-phenylpropionyl ester, and (1)H, (1)H COSY NMR spectroscopy of synthesized (5'R)-configured stereoisomers, synthesized from (R)-linalool. Direct stereodifferentiation of the eight stereoisomers of lilac aldehyde and lilac alcohol, respectively, has been achieved, using enantioselective capillary GC. The elution order of the isomers was deduced from the chromatographic behavior of the (5'R)-configured diastereoisomers. Additionally, the odor thresholds of lilac aldehyde and lilac alcohol stereoisomers are reported.
Kreck
Mirjam
M
Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universität, Marie-Curie Strasse 9, D-60439 Frankfurt Main, Germany.
Mosandl
Armin
A
D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D009812:Odorants / Q000032:analysis; D013237:Stereoisomerism; D031662:Syringa / Q000737:chemistry*
D000438:Alcohols; D000447:Aldehydes