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Synthesis and Olfactory Properties of Seco-Analogues of Lilac Aldehydes.

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.

SUBMITTER: Dacho V

PROVIDER: S-EPMC8658798 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Synthesis and Olfactory Properties of Seco-Analogues of Lilac Aldehydes.

Dacho Vladimír V Szolcsányi Peter P

Molecules (Basel, Switzerland) 20211123 23

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 accompan ...[more]

PMID: 34885667

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