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Chirospecific analysis in flavor and essential oil chemistry Part B. Direct enantiomer resolution of frans-α-ionone and trans-α-damascone by inclusion gas chromatography

Chirale Analysen von Aroma-und etherischen Öl-Inhaltsstoffen Teil B. Direkte Trennung der Enantiomeren von trans-α-Ionon und trans-α-Damascon mittels Inklusionsgaschromatographie

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Zusammenfassung

Mit Heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin in Polysiloxan als chiraler stationärer GC-Phase können die Enantiomeren vontrans-α-Ionon undtrans-α-Damascon direkt stereodifferenziert werden. Mit der beschriebenen Methode wird die Enantiomerenzusammensetzung vontrans-α-Ionon in den Absolues vonBoronia megastigma Nées undOsmanthus fragrance Lour., in Costuswurzelöl (Saussurea lappa Clarke), in den Headspace-Konzentraten von Veilchenblüten, frischen Himbeeren, Karotten und Vanilleschoten sowie in den Lösungsmittelextrakten von Himbeergeist, Himbeerfruchtsaftkonzentrat und schwarzem Tee bestimmt.Trans-α-Ionon wurde aus den genannten Naturprodukten mit Hilfe von multidimensionalen präparativen chromatographischen Trenntechniken angereichert und isoliert.Trans-α-Damascon wurde durch die Kombination MPLC/präparative Capillargaschromatographie aus Virginia Tabakextrakt und aus dem Aromastoffspektrum von schwarzem Tee erhalten und in s eine Enantiomeren aufgetrennt. Die Bedeutung der Chiralität als Beurteilungskriterium zur Unterscheidung natürlicher und naturidentischer Aromastoffe wird kurz diskutiert.

Summary

The direct capillary gas Chromatographic separation oftrans-α-ionone andtrans-α-damascone enantiomers is reported using heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin in polysiloxane as a suitable chiral stationary phase. The method described has been applied to determine the naturally occurring enantiomeric composition oftrans-α-ionone in the absolutes of the flowers ofBoronia megastigma Nees andOsmanthus fragrance Lour., Costus root oil (Saussurea lappa Clarke) as well as in odor concentrates of violet flowers (Viola odorata L.), fresh raspberries, carrots and vanilla pods. Furthermore, the optical purity oftrans-α-ionone in the solvent extracts of distilled alcoholic raspberry beverage, raspberry fruit juice concentrate and black tea was investigated.Trans-α-ionone was either isolated by headspace stripping in vacuo or by organic solvent extraction and subsequently enriched by multidimensional preparative Chromatographic techniques.Trans-α-damascone was isolated from Virginia tobacco extract and from black tea aroma and was enriched for direct chirospecific analysis by medium pressure liquid chromatography followed by multidimensional preparative capillary gas chromatography. The importance of chirality as an essential criterion for the discrimination of natural and nature-identical aromas is discussed briefly.

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Authors and Affiliations

  1. Research Department, Haarmann & Reimer GmbH, W-3450, Holzminden, Federal Republic of Germany

    Peter Werkhoff, Wilfried Bretschneider, Matthias Güntert, Rudolf Hopp & Horst Surburg

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  1. Peter Werkhoff
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  2. Wilfried Bretschneider
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  3. Matthias Güntert
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  4. Rudolf Hopp
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  5. Horst Surburg
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Werkhoff, P., Bretschneider, W., Güntert, M. et al. Chirospecific analysis in flavor and essential oil chemistry Part B. Direct enantiomer resolution of frans-α-ionone and trans-α-damascone by inclusion gas chromatography. Z Lebensm Unters Forch 192, 111–115 (1991). https://doi.org/10.1007/BF01202622

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  • DOI: https://doi.org/10.1007/BF01202622

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