Abstract
Lilac aldehydes are considered as principal olfactory molecules of lilac flowers. We have designed, prepared, and evaluated a set of racemic seco-analogues of such natural products. The synthesis employs commercially available α-chloroketones as substrates that are transformed in four steps to target compounds. Their qualitative olfactory analysis revealed that the opening of the tetrahydrofuran ring leads to a vanishing of original flowery scent with the emergence of spicy aroma accompanied by green notes, and/or fruity aspects of novel seco-analogues. These results suggest the important osmophoric role of THF moiety for the generation of the typical flowery aroma associated with lilac aldehydes.
Highlights
Lilac aldehydes are being developed as chemical markers of the botanical origin of honeys [15,16,17,18]
The preparation of novel seco-analogues 3–7 features a common synthetic strategy that starts with an acid-catalysed ketalisation of commercially available α-chloroketones
Ring-opened analogues 3–5 bearing an acyclic alkene exhibit a rather common spicy, sharp aroma with green/herbal notes. The scent of their congeners featuring a cyclic alkene is further shifted towards sweet, fruity aspects for 6 and herbal, green notes for 7
Summary
The biosynthesis of lilac aldehydes was proposed and investigated [3] Since these naturally occurring monoterpenes were found in flowers of many other species, including kiwifruit [4], the White Campion [5], and the Lesser Butterfly orchid [6]. It is known that these flower-scenting molecules are much sought after by (nocturnal) moth species [7,8,9], butterflies [10,11], and even mosquitos [12,13,14] In this context, lilac aldehydes are being developed as chemical markers of the botanical origin of honeys [15,16,17,18].
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