3691-12-1Relevant articles and documents
Revisiting the Chemistry of Guaiacwood Oil: Identification and Formation Pathways of 5,11- and 10,11-Epoxyguaianes
Tissandié, Lo?c,Gaysinski, Marc,Brévard, Hugues,Meierhenrich, Uwe J.,Filippi, Jean-Jacques
, p. 526 - 537 (2017/03/09)
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.
Effective analysis of rotundone at below-threshold levels in red and white wines using solid-phase microextraction gas chromatography/tandem mass spectrometry
Mattivi,Caputi,Carlin,Lanza,Minozzi,Nanni,Valenti,Vrhovsek
experimental part, p. 483 - 488 (2012/02/02)
Rotundone is an oxygenated sesquiterpene belonging to the family of guaianes, giving the 'peppery' aroma to white and black pepper and to red wines. Here we describe a novel, convenient protocol for the synthesis of rotundone, starting from a commercially available compound and requiring only two reaction steps, and an improved, faster method of GC separation (30min) with selective quantisation of rotundone using tandem mass spectrometry in multiple reaction monitoring (MRM) mode with d5-rotundone as internal standard. With limits of detection (LODs) of 1.5ng/L in white wine and 2.0ng/L in red wine, intraday repeatability CV values of 6% and 5% at 50ng/L and 500ng/L and interday repeatability CV values of 13% and 6% at 50ng/L and 500ng/L, respectively, the improved protocol provides the desired sensitivity and selectivity for routine analysis of rotundone in both white and red wines. Initial application of this method highlighted the presence of unexpectedly high concentrations of rotundone, thus explaining the origin of the distinctive peppery aroma in Schioppettino and Vespolina red wines and in Gruener Veltliner white wines.
A Simple Synthesis of (-)-Rotundone from Guaiol
Paknikar, S. K.,Kamat, V. P.
, p. 1060 (2007/10/02)
(-)-Rotundone (1) has been prepared in 40 percent yield by t-butyl chromate oxidation of guaiene (4) obtainable from naturally occuring guaiol (5).