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Light‐induced controlled release of fragrance aldehydes from 1‐alkoxy‐9,10‐anthraquinones for applications in functional perfumery
Author(s) -
Levrand Barbara,
Herrmann Andreas
Publication year - 2006
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.1728
Subject(s) - chemistry , anthraquinones , alkoxy group , organic chemistry , aldehyde , catalysis , alkyl , botany , biology
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.