title: Enzyme-triggered and self-cleaving fragrant alcohol precursors.
abstract: The high volatility and water solubility of many natural perfumery alcohols leads to their rapid loss in fabric-care and personal-care applications. A dramatically enhanced substantivity is achieved by the use of fragrance precursors as controlled-release systems. In the first part of this article, we present multi-odorant precursors, in which the enzymatic cleavage of esters or carbonates of fragrant alcohols triggers subsequent steps leading to the release of fragrant ketones, lactones, and additional fragrant alcohols. In the second part, a study on oligocarbonates of fragrant alcohols is presented. Therein, the outstanding enzyme-independent performance of gluconolactone oligocarbonate 27 for the long-lasting release of (Z)-hex-3-en-1-ol is highlighted. We show that these polyfunctional compounds undergo complex rearrangements and intramolecular substitution reactions which lead to the observed release kinetics.
authors.affiliation: Fragrance Research, Givaudan Schweiz AG, Uberlandstrasse 138, CH-8600 Dübendorf. felix.flachsmann@givaudan.com
authors.forename: Felix
authors.initials: F
authors.lastname: Flachsmann
authors.forename: Markus
authors.initials: M
authors.lastname: Gautschi
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Bachmann
authors.forename: Gerhard
authors.initials: G
authors.lastname: Brunner
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D001365:Axilla / Q000382:microbiology; D002384:Catalysis; D003352:Corynebacterium / Q000201:enzymology*; D006801:Humans; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D010476:Perfume / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000438:Alcohols; D010476:Perfume; D008049:Lipase