The Quest For Odorants Having Salicylate Notes

We describe the synthesis and sensory characterization of a series of compounds which we anticipated would possess the olfactory notes of salicylates. We explored carba-analogues, cyclic -keto esters and cyclic -diketones as salicylate analogues. Applying the simple concept of three-dimensional structure similarity was very fruitful. Salicylate carba-analogues and -keto esters, especially compounds 5, 7 and 10 for the first series and 27 and 28 for the second series, proved to be the most interesting type of compounds. For example, 1-(2-hydroxyphenyl)-3-phenyl-1-propanone (10), which can be found in nature, is nicely diffusive and has an excellent olfactory profile with an interesting dual floral-animal note. In general, these compounds may offer a first credible alternative to the popular salicylates. Copyright (c) 2013 John Wiley & Sons, Ltd.