title: Enantiodifferentiation of 1,2-propanediol in various wines as phenylboronate ester with multidimensional gas chromatography-mass spectrometry.
abstract: Native concentrations and enantiomeric distribution of 1,2-propanediol in various wines were studied in order to evaluate its merits as a potential marker for aroma adulteration in wine. Heart-cut multidimensional gas chromatography coupled to mass spectrometry was applied to analyze 1,2-propanediol after salting-out of the polar phase, derivatization with phenyl boronic acid, and extraction with cyclohexane. The enantiomeric separation of the derivative was achieved with heptakis-(6-O-tert. butyl dimethylsilyl-2,3-di-O-acetyl)-β-cyclodextrin as the chiral selector. In all authentic wines studied, 1,2-propanediol showed a high enantiomeric ratio in favor of the (R)-enantiomer, proving its potential as a marker for the adulteration with flavor extracts based on industrial 1,2-propandiol as solvent. Usually, concentrations varied between 15 and 100 mg/L. Higher values (up to 170 mg/L) were found in wines made with high amounts of dry berries. However, despite the higher concentrations of 1,2-propanediol in such wines, no apparent influence on the enantiomeric distribution could be detected. Graphical Abstract Detection of fraudulent aromatization of wines by enantiodifferentiation of 1,2-propanediol as its phenylboronate ester.
authors.affiliation: Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, Institut für Weinbau und Oenologie, Breitenweg 71, 67435, Neustadt an der Weinstraße, Germany.|Universität Duisburg-Essen, Fakultät für Chemie, Universitätsstraße 5, 45141, Essen, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Langen
authors.affiliation: Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, Institut für Weinbau und Oenologie, Breitenweg 71, 67435, Neustadt an der Weinstraße, Germany.
authors.forename: Ulrich
authors.initials: U
authors.lastname: Fischer
authors.affiliation: Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, Institut für Weinbau und Oenologie, Breitenweg 71, 67435, Neustadt an der Weinstraße, Germany.|Hochschule Mannheim, Fakultät für Verfahrens- und Chemietechnik, Paul-Wittsack-Str. 10, 68163, Mannheim, Germany.
authors.forename: Marc
authors.initials: M
authors.lastname: Cavalar
authors.affiliation: Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, Institut für Weinbau und Oenologie, Breitenweg 71, 67435, Neustadt an der Weinstraße, Germany.|Department of Viticulture and Oenology, Stellenbosch University, Private Bag X1, 7602, Matieland, South Africa.
authors.forename: Carien
authors.initials: C
authors.lastname: Coetzee
authors.affiliation: Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, Institut für Weinbau und Oenologie, Breitenweg 71, 67435, Neustadt an der Weinstraße, Germany.
authors.forename: Pascal
authors.initials: P
authors.lastname: Wegmann-Herr
authors.affiliation: Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, Institut für Weinbau und Oenologie, Breitenweg 71, 67435, Neustadt an der Weinstraße, Germany. hans-georg.schmarr@dlr.rlp.de.|Universität Duisburg-Essen, Fakultät für Chemie, Universitätsstraße 5, 45141, Essen, Germany. hans-georg.schmarr@dlr.rlp.de.
authors.forename: Hans-Georg
authors.initials: HG
authors.lastname: Schmarr
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D004952:Esters; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D019946:Propylene Glycol / Q000032:analysis*; D013237:Stereoisomerism; D014920:Wine / Q000032:analysis*
chemical_list: D001897:Boronic Acids; D004952:Esters; D019946:Propylene Glycol; C010686:benzeneboronic acid
keywords: 1,2-Propanediol; Adulteration; Enantiodifferentiation; Heart-cut multidimensional gas chromatography; Mass spectrometric detection; Phenyl boronic acid