Synthesis and olfactory properties of unnatural derivatives of lilac aldehydes |
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Authors: | Peter Šiška Peter Fodran Peter Szolcsányi |
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Institution: | 1. Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia;2. Department of Nutrition and Food Assessment, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia;3. FLOP Ltd., Mandl''ová 37, SK-851 10 Bratislava, Slovakia |
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Abstract: | Lilac aldehydes are considered as principal olfactory molecules of lilac flowers. We have designed, prepared and evaluated two sets of their unnatural racemic analogues as pure diastereomers. While the synthesis of gem-dimethyl homologues starts from geranyl acetate, the preparation of methylene derivatives commences from linalyl acetate. The key Lewis and/or Brønsted acid catalysed cyclisation furnishes easily separable cis-/trans-tetrahydrofuranyl esters as common advanced intermediates. The subsequent functional group transformations lead to target aldehydes, alcohols, nitriles and olefins. Unlike the homologues possessing similar herbal scents, methylene derivatives exhibit woody and/or flowery odours. In the latter case, the sensory evaluation suggests the importance of relative stereochemistry and/or type of functional group on the odour character of respective compounds. |
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Keywords: | Terpenes Tetrahydrofurans Homologues Natural products Olfactory evaluation |
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