title: Thioether profragrances: parameters influencing the performance of precursor-based fragrance delivery in functional perfumery.
abstract: A series of thioether profragrances was prepared by reaction of different sulfanylalkanoates with δ-damascone and tested for their release efficiencies in a fabric-softener and an all-purpose cleaner application. Dynamic headspace analysis on dry cotton and on a ceramic plate revealed that the performance of the different precursors depended on the structure, but also on the particular conditions encountered in different applications. Moreover, profragrances derived from other α,β-unsaturated fragrance aldehydes and ketones were synthesized analogously and evaluated using the same test protocol. Thioethers were found to be suitable precursors to release the corresponding fragrances, but neither the quantity of profragrance deposited from an aqueous environment onto the target surface, nor the amount of fragrance released after deposition could be linearly correlated to the hydrophilicity or hydrophobicity of the compounds. Different sets of compounds were found to be the best performers for different types of applications. Only one of the compounds evaluated in the present work, namely the thiolactic acid derivative of δ-damascone, efficiently released the corresponding fragrance in both of the tested applications. Profragrance development for functional perfumery thus remains a partially empirical endeavour. More knowledge (and control) of the various application conditions are required for an efficient profragrance design.
authors.affiliation: Firmenich SA, Division Recherche et Développement, Route des Jeunes 1, B. P. 239, CH-1211 Genève 8.
authors.forename: Umberto
authors.initials: U
authors.lastname: Maddalena
authors.forename: Alain
authors.initials: A
authors.lastname: Trachsel
authors.forename: Peter
authors.initials: P
authors.lastname: Fankhauser
authors.forename: Damien L
authors.initials: DL
authors.lastname: Berthier
authors.forename: Daniel
authors.initials: D
authors.lastname: Benczédi
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Xiujuan
authors.initials: X
authors.lastname: Xi
authors.forename: Youqing
authors.initials: Y
authors.lastname: Shen
authors.forename: Andreas
authors.initials: A
authors.lastname: Herrmann
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010476:Perfume / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013997:Time Factors
chemical_list: D000447:Aldehydes; D004987:Ethers; D007659:Ketones; D010476:Perfume; D013438:Sulfhydryl Compounds
keywords: Controlled release; Damascones; Fragrance delivery; Profragrances; Thioethers