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Abstract
Five new bulky moiety-modified analogues of the sandalwood odorant Polysantol® have been synthesized by aldol condensation of appropriate aldehydes with butanone, deconjugative α-methylation of the resulting α,β-unsaturated ketones, and reduction of the corresponding β,γ-unsaturated ketones. The final compounds were evaluated organoleptically and one of them seemed to be of special interest for its natural sandalwood scent.
Highlights
Introduction(–)-(Z)-β-Santalol (1), the main constituent of natural sandalwood oil, is an odour compound with typical sandalwood fragrance and is described as warm-woody, creamy and sweet with an animalic tonality [1,2]
Polysantol® have been synthesized by aldol condensation of appropriate aldehydes with butanone, deconjugative -methylation of the resulting -unsaturated ketones, and reduction of the corresponding -unsaturated ketones
As other authors have done [7,8,25], we have studied the influence of the global shape of the hydrophobic moiety C, and for the refinement of the olfactophore model on compounds structurally similar to Polysantol®, five new compounds 33−37 (Figure 3) have been synthesized for this work and their odour evaluated
Summary
(–)-(Z)-β-Santalol (1), the main constituent of natural sandalwood oil, is an odour compound with typical sandalwood fragrance and is described as warm-woody, creamy and sweet with an animalic tonality [1,2] It consists of a bulky bicyclic moiety separated from the hydroxyl group by an unsaturated 5 C-atoms spacer [3]. As is well known [3,11], three subunits are important for the sandalwood odour impression (Figure 1), which correspond to the hydroxyl group (A), a lipophilic substituent (B) in the neighbourhood of this hydroxyl group, and a bulky rigid hydrophobic moiety (C) This set of structural features constitutes the sandalwood olfactophore. These molecules have been obtained from the aldehydes 12 15 and 18, respectively, through a straightforward process involving the aldol condensation of each starting aldehyde with butanone, the deconjugative α-methylation of the respective enones and the reduction of the corresponding -unsaturated ketone to yield every alcohol analogue to the odorant Polysantol® (see Scheme 2 below)
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