Enantiomeric Composition of Filbertone in Hazelnuts in Relation to Extraction Conditions. Multidimensional Gas Chromatography and Gas Chromatography/Mass Spectrometry in the Single Ion Monitoring Mode of a Natural Sample

Abstract

The influence of the matrix and the isolation and concentration conditions on the enantiomeric excess of filbertone [(E)-5-methyl-2-hepten-4-one] in hazelnuts is studied. In hazelnuts, under mild conditions the filbertone obtained has a higher enantiomeric excess than that one extracted under forced conditions. Enantiomers were separated by inclusion gas chromatography on Chirasil-β-Dex using multidimensional gas chromatography with flame ionization detection and gas chromatography/mass spectrometry in the selected ion monitoring mode. Keywords: Filbertone; enantiomeric excess; multidimensional gas chromatography

Study of the enantiomeric composition of chiral constituents in edible oils by simultaneous distillation‐extraction. Detection of adulterated olive oils

“…On the other hand, the enantiomeric distribution of filbertone may not be influenced by extraction and isolation conditions and, moreover, filbertone does not show a tendency for partial racemization in response to heat. In any case, the temperature used in this work during SDE operation is slightly higher than those reported in the literature (140 vs. 100-120°C) for racemization studies of filbertone (23). Consequently, racemization due to heat should not be excluded although the low enantiomeric excess obtained is more likely due to the shift of the enantiomeric excess to a higher (R)-content that may be caused by the presence of a unknown precursor in the hazelnut matrix which forms racemic filbertone by a chemical mechanism as previously suggested (23).…”

Enantiomeric composition of filbertone in hazelnuts and hazelnut oils from different geographical origins

“…Taking into account that the variation of the enantiomeric composition of the total content of a chiral compound can be caused under different experimental conditions (15,20,21), we considered it essential to minimize or even eliminate the sample preparation step and avoid heating the sample. Finally, we selected the two approaches described in the Experimental Procedures section, which involved either the cold extraction of the sample (hazelnut or hazelnut oil) with organic solvents and its subsequent analysis by GC, or the analysis by on-line coupled LC-GC.…”

Separation of Enantiomers by Gas Chromatography on Chiral Stationary Phases

“…Here the first nonenantioselective column, coated with an achiral polar stationary phase, is used to pre-separate components of interest (first dimension), whereas in the second enantioselective column, coated with a CSP, fractions of chiral analytes are enantioseparated after on-line transfer through a pneumatic or flow-controlled low-dead-volume heart-cut interface (second dimension). There are many applications in the field of terpenes and food chemistry [184][185][186][187][188][189]. The traditional one-column operation has been compared with enantio-MDGC for the enantioseparation of monoterpenes from essential oils [190].…”