Mimicking the pineapple scent: Synthesis and properties of (semi)conjugated triene carbonyl derivatives |
| |
Authors: | Peter Šiška Daniela Danková Dária Nitrayová Peter Fodran Ivan Špánik |
| |
Institution: | 1. Department of Organic Chemistry, Slovak University of Technology, Bratislava, Slovakia;2. Department of Nutrition and Food Assessment, Slovak University of Technology, Bratislava, Slovakia;3. Department of Analytical Chemistry, Slovak University of Technology, Bratislava, Slovakia |
| |
Abstract: | The unexpected formation of previously nondescribed (semi)conjugated ethyl trienoate revealed its powerful aroma of fresh pineapple. Thus, we have designed, prepared and evaluated a set of its carbonyl analogues as mixtures of (E/Z)-isomers. Although their synthesis from natural ocimene led to target compounds in low yields, optimized preparation from geranyl acetate furnished an aldehyde as high-yielding common intermediate on multigram scale. A series of its Wittig olefinations provided corresponding (E,E)-configured carbonyl dienes. Final acid-catalyzed elimination of allylic acetates provided the desired “pineapple” target in moderate yield. Sensory analysis revealed that only the parent compound possesses the typical pineapple aroma. Although analogous tBu- and/or Bn-esters feature an additional green note, the most similar Me-ester differs by its fresh woody aroma analogously to methyl ketone. |
| |
Keywords: | Pineapple aroma polyenes unsaturated esters Wittig reaction |
|
|