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Enantiomeric ratios of pantolactone, solerone, 4-carboethoxy-4-hydroxy-butyrolactone and of sotolon, a flavour impact compound of flor-sherry and botrytized wines

Enantiomerenverhältnisse von Pantolacton, Soleron, 4-Carbethoxy-4-hydroxy-butryolacton und Sotolon, einer Aromaleitsubstanz von Flor-Sherry und Botrytris-Weinen

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Zusammenfassung

Die Synthese der Enantiomeren des Sotolons (2), einer Aromaleitsubstanz für Flor-Sherryund Botrytis-Weine, wird aufgezeigt und das chromatographische Verhalten der Enantiomeren (R)-2 und (S)-2 an permethyliertemβ-Cyclodextrin bestimmt. Mittels enantioselektiver multidimensionaler Gaschromatographie (Säulenkombination: DB 1701/Permethyl-β-Cyclodextrin) werden die Enantiomerenverhältnisse der chiralenγ-Lactone Pantolacton (1), Sotolon (2), Soleron (3) und 4-Carbethoxy-4-hydroxybutyrolactone (4) in Flor-Sherry- und Botrytis-Weinen ermittelt. Während für die Lactone1 und4 hohe Enantiomerenüberschüsse zugunsten der (4R)-konfigurierten Spiegelbildisomere nachgewiesen werden, können aus dem für Soleron (3) bzw. Sotolon (2) ermittelten Enantiomerenverhältnissen keine Rückschlüsse auf die Authentizität dieser Verbindungen abgeleitet werden.

Summary

The enantiomers of sotolon (2), a flavour impact compound of flor-sherry and botrytized wines, were synthesized to determine the Chromatographic behaviour of the enantiomers (R)-2 and (S)-2 on permethylatedβ-cyclodextrin as the chiral stationary phase. Using enantioselective multidimensional gas chromatography (column combination: DB 1701/permethyl-β-cyclodextrin) the enantiomeric ratios of the chiralγ-lactones pantolactone (1), sotolon (2), solerone (3) and 4-carboethoxy-4-hydroxy butyrolactone (4) in flor-sherry and botrytized wines were evaluated. High enantiomeric excess in favour of the (4R)-configurated mirror images was detected for lactones1 and4. The measured enantiomeric ratios of sotolon (2) and solerone (3) were too low and unspecific to be useful in authenticity control of2 and3.

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Authors and Affiliations

  1. Laboratoire de Recherches sur les Arômes, Institut National de la Recherche Agronomique, B.V.1540, F-21034, Dijon Cedex, France

    Elisabeth Guichard & Patrick Etiévant

  2. Laboratoire de chimie organique, Institut National des Sciences appliquées, Bat 403, F-69621, Villeurbanne Cedex, France

    Robert Henry

  3. Institut für Lebensmittelchemie, Universität Frankfurt, Robert-Mayer-Strasse 7-9, W-6000, Frankfurt am Main, Germany

    Armin Mosandl

Authors
  1. Elisabeth Guichard
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  2. Patrick Etiévant
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  3. Robert Henry
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  4. Armin Mosandl
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Guichard, E., Etiévant, P., Henry, R. et al. Enantiomeric ratios of pantolactone, solerone, 4-carboethoxy-4-hydroxy-butyrolactone and of sotolon, a flavour impact compound of flor-sherry and botrytized wines. Z Lebensm Unters Forch 195, 540–544 (1992). https://doi.org/10.1007/BF01204559

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  • DOI: https://doi.org/10.1007/BF01204559

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