Synthesis and sensorial properties of 2-alkylalk-2-enals and 3-(acetylthio)-2-alkyl alkanals.
Parallel synthesis was applied to prepare a series of 3-(acetylthio)-2-alkyl alkanals by Michael addition of thioacetic acid under alkaline conditions to alpha,beta-unsaturated 2-alkyl-substituted aldehydes, which were obtained by aldol condensation of the corresponding primary aldehydes as starting materials. The target compounds were characterized in terms of GC, MS, and NMR data. The sensory properties of the odorants, such as odor quality and odor detection threshold value, were determined with a trained panel. Structure-activity relationships are discussed, suggesting that the 1,3-oxygen-sulfur functionality, required for the "olfactophore" of tropical/vegetable notes, can further be extended to the acetylthio derivatives.
Robert
Fabien
F
Nestec Ltd, Nestlé Research Center, Vers-chez-les-Blanc, PO Box 44, 1000 Lausanne 26, Switzerland.
Héritier
Julien
J
Quiquerez
Joelle
J
Simian
Hervé
H
Blank
Imre
I
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009812:Odorants; D012903:Smell; D013329:Structure-Activity Relationship
D000447:Aldehydes; D000473:Alkanes; D000475:Alkenes