Light-induced controlled release of fragrance aldehydes from 1-alkoxy-9,10-anthraquinones for applications in functional perfumery

Authors


  • Dedicated to Dr Ferdinand Näf on the occasion of his 65th birthday.

  • Parts of this work were presented at the Fall Meeting of the Swiss Chemical Society, Lausanne, Switzerland, 13 October 2005; see Herrmann A. Chimia 2005; 59: 639 (abstr 235).

Abstract

Light-activated chemical delivery systems for the controlled release of fragrances have been shown to be effective in functional perfumery. Upon photolysis around 350 nm, 1-alkoxy-9,10-anthraquinones release aldehydes or ketones and may thus be considered as promising precursors for the photochemical release of perfume molecules. A series of substituted and unsubstituted mono- and dialkoxy-9,10-anthraquinones was prepared by reaction of the corresponding fragrance bromides with commercial mono- or dihydroxy-9,10-anthraquinones. Photoirradiation of these compounds in polar and apolar solution yielded the desired fragrance aldehydes. Preliminary olfactory panel evaluations on fabric after exposure to ambient indoor daylight for several days indicated a slightly stronger odour in the presence of the fragrance precursors, as compared to a reference sample containing the unmodified perfumery raw material. Copyright © 2006 John Wiley & Sons, Ltd.

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