title: Revisiting the Chemistry of Guaiacwood Oil: Identification and Formation Pathways of 5,11- and 10,11-Epoxyguaianes.
abstract: Guaiacwood oil from Bulnesia sarmientoi Lorentz ex. Griseb is a common natural ingredient of the perfume industry used in both domestic and luxury fragrances for its highly appreciated woody-rosy odor, as well as its excellent fixative properties. Despite its long and traditional use as a perfume ingredient, guaiacwood oil has not been extensively studied. Thus, the chemical characterization of its constituents by using a full array of GC-hyphenated techniques (GC-MS, GC × GC-MS, and pc-GC) combined with conventional chemical fractionation was undertaken. In the course of this work, 15 new sesquiterpenoids mostly belonging to the 5,11- and 10,11-epoxyguaiane families were identified. Each isolated compound was fully characterized by NMR and MS. Collectively, the specific chemical relationships observed between sesquiterpene oxides and alcohols permitted the formulation of probable formation pathways regarding their presence as natural constituents of guaiacwood extracts.
authors.affiliation: Institut de Chimie de Nice, Université Côte d'Azur , UMR 7272 CNRS, Parc Valrose, 06108 Nice Cedex 2, France.
authors.forename: Loïc
authors.initials: L
authors.lastname: Tissandié
authors.affiliation: Institut de Chimie de Nice, Université Côte d'Azur , UMR 7272 CNRS, Parc Valrose, 06108 Nice Cedex 2, France.
authors.forename: Marc
authors.initials: M
authors.lastname: Gaysinski
authors.affiliation: Robertet S.A. , 37 Avenue Sidi Brahim, 06130 Grasse, France.
authors.forename: Hugues
authors.initials: H
authors.lastname: Brévard
authors.affiliation: Institut de Chimie de Nice, Université Côte d'Azur , UMR 7272 CNRS, Parc Valrose, 06108 Nice Cedex 2, France.
authors.forename: Uwe J
authors.initials: UJ
authors.lastname: Meierhenrich
authors.affiliation: Institut de Chimie de Nice, Université Côte d'Azur , UMR 7272 CNRS, Parc Valrose, 06108 Nice Cedex 2, France.
authors.forename: Jean-Jacques
authors.identifier: 0000-0001-5701-8912
authors.initials: JJ
authors.lastname: Filippi
mesh_terms: D053898:Biosynthetic Pathways; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009822:Oils, Volatile / Q000737:chemistry*; D010938:Plant Oils / Q000737:chemistry*; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry*
chemical_list: D009822:Oils, Volatile; D010938:Plant Oils; D045789:Sesquiterpenes, Guaiane