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Original Articles

Enantioselective capillary gas chromatography and stable isotope ratio mass spectrometry in the authenticity control of flavors and essential oils

Pages 597-664 | Published online: 03 Nov 2009

References

  • Russell , G. F. and Hills , J. I. 1971 . Odor differences between enantiomeric isomers . Science , 172 : 1043
  • Friedman , L. and Miller , J. G. 1971 . Odor incongruity and chirality . Science , 172 : 1044
  • Mosandl , A. and Heusinger , G. 1985 . 1,3‐Oxathianes, chiral fruit flavour compounds . Liebigs Ann. Chem. , : 1185 – 1191 .
  • Ohloff , G. 1986 . Chemistry of odor stimuli . Experientia , 42 : 271 – 279 .
  • Günther , C. and Mosandl , A. 1986 . Stereoisomere Aromastoffe XII: 3‐MethyI‐4‐octanolid‐“Quer‐cuslacton, Whiskylacton”—Struktur und Eigenschaften der Stereoisomeren . Liebigs Ann. Chem. , : 2112 – 2122 .
  • Mosandl , A. , Heusinger , G. and Gessner , M. 1986 . Analytical and sensory differentiation of 1‐octen‐3‐ol enantiomers . J. Agric. Food Chem. , 34 : 119 – 122 .
  • Mosandl , A. and Gessner , M. 1988 . Stereoisomeric flavour compounds XXIII: δ‐lactone flavour compounds —structure and properties of the enantiomers . Z. Lebensm. Unters. Forsch. , 187 : 40 – 44 .
  • Mosandl , A. and Günther , C. 1989 . Stereoisomeric flavor compounds. XX: Structure and properties of γ‐lactone enantiomers . J. Agric. Food Chem. , 37 : 413 – 418 .
  • Ohloff , G. 1990 . “Riechstoffe und Geruchssinn—Die molekulare Welt der Düfte” , Berlin : Springer‐Verlag .
  • Bauer , K. , Garbe , D. and Surburg , H. 1990 . “Common Fragrance and Flavor Materials, Preparation, Properties and Uses” , 2nd ed. , Weinheim : VCH .
  • Mosandl , A. 1992 . Capillary gas chromatography in quality assessment of flavours and fragrances . J. Chromatogr. , 624 : 267 – 292 .
  • Sandra , P. 1989 . Resolution—definition and nomenclature . J. High Resolut. Chromatogr. , 12 : 82 – 86 .
  • König , W. A. 1990 . Modifizierte Cyclodextrine als chirale Trennphasen in der Gaschromatographie . Kontakte (Darmstadt) , : 3 – 14 .
  • König , W. A. , Krüger , A. , Icheln , D. and Runge , T. 1992 . Enantiomeric composition of the chiral constituents in essential oils. Part 1: Monoterpene hydrocarbons . J. High Resolut. Chromatogr. , 15 : 184 – 189 .
  • König , W. A. , Gehrcke , B. , Icheln , D. , Evers , P. , Doennecke , J. and Wang , U. 1992 . New, selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils . J. High Resolut. Chromatogr. , 15 : 367 – 372 .
  • Mosandl , A. , Heusinger , G. , Wistuba , D. and Schurig , V. 1984 . Analysis of a chiral aroma compound by complexation gas chromatography . Z. Lebensm. Unters. Forsch. , 179 : 385 – 386 .
  • Deger , W. , Gessner , M. , Heusinger , G. , Singer , G. and Mosandl , A. 1986 . Stereoisomeric flavor compounds. XIII: Critical remarks on the interpretation of chiral Stereodifferentiation in gas chromatography . J. Chromatogr. , 366 : 385 – 390 .
  • König , W. A. , Lutz , S. , Mischnick‐Lübbecke , P. , Brassat , B. and Wenz , G. 1988 . Cyclodextrins as chiral stationary phases in capillary gas chromatography. I. Pentylated a‐cyclodextrin . J. Chromatogr. , 447 : 193 – 197 .
  • Mosandl , A. and Hagenauer‐Hener , U. 1988 . Stereoisomeric flavor compounds. XXVI: HRGC Analysis of chiral 1,3‐dioxolanes . J. High Resolut. Chromatogr. Chromatogr. Comra. , 11 : 744 – 749 .
  • König , W. A. , Icheln , D. and Hardt , I. 1991 . Unusual retention behaviour of methyl lactate and methyl 2‐hydroxybutyrate enantiomers on a modified cyclodextrin . J. High Resolut. Chromatogr. , 14 : 694 – 695 .
  • Mosandl , A. , Rettinger , K. , Fischer , K. , Schubert , V. , Schmarr , H.‐G. and Maas , B. 1990 . Stereoisomeric flavor compounds. XLI: New applications of permethylated β‐cyclodextrin phase in chiral CGC analysis . J. High Resolut. Chromatogr. , 13 : 382 – 385 .
  • König , W. A. , Lutz , S. , Colberg , C. , Schmidt , N. , Wenz , G. , von der Bey , E. , Mosandl , A. , Günther , C. and Kustermann , A. 1988 . Cyclodextrins as chiral stationary phases in capillary gas chromatography, Part III: Hexakis (3‐O‐acetyl‐2,6‐di‐O‐penty1)‐α‐cyclodextrin . J. High Resolut. Chromatogr. Chromatogr. Comm. , 11 : 621 – 625 .
  • Kreis , P. , Mosandl , A. and Schmarr , H.‐G. 1990 . Mentha‐Öle, enantioselektive Analyse des Men‐thylacetats zur Qualitätsbeurteilung von Mentha‐Ölen . Dtsch. Apoth. Ztg. , 130 : 2579 – 2581 .
  • Kreis , P. , Juchelka , D. , Motz , C. and Mosandl , A. 1991 . Chirale Inhaltsstoffe ätherischer Öle. IX: Stereodifferenzierung von Borneol, Isoborneol und Bornylacetat . Dtsch. Apoth. Ztg. , 131 : 1984 – 1987 .
  • Mosandl , A. and Kustermann , A. 1989 . Stereoisomere Aromastoffe. XXX: HRGC‐Analyse chir‐aler γ‐Lactone aus Getränken und Fruchtzubereitungen . Z. Lebensm. Unters. Forsch. , 189 : 212 – 215 .
  • Mosandl , A. , Kustermann , A. , Palm , U. , Dorau , H.‐P. and König , W. A. 1989 . Stereoisomeric flavour compounds. XXVIII: Direct chirospecific HRGC‐analysis of natural γ‐lactones . Z. Lebensm. Unters. Forsch. , 188 : 517 – 520 .
  • Schmarr , H.‐G. , Mosandl , A. and Grob , K. 1990 . Stereoisomeric Flavour Compounds. XXXVIH: Direct chirospecific analysis of 7‐lactones using on‐line coupled HPLC‐HRGC with a chiral separation column . Chromatographia , 29 : 125 – 130 .
  • Artho , A. and Grob , K. 1990 . Nachweis der Aromatisierung von Lebensmitteln mit γ‐Lactonen. Wie identisch mit der Natur müssen “naturidentische” Aromen sein? . Mitt. Gebiete Lebensm. Hyg. , 81 : 544 – 558 .
  • Wang , C. , Frank , H. , Wang , G. , Zhou , L. , Beyer , E. and Lu , P. 1983 . Determination of amino acid enantiomers by two‐column gas chromatography with valveless column switching . J. Chro‐matogr. , 262 : 352 – 359 .
  • Schomburg , G. , Husmann , H. , Hübinger , E. and König , W. A. 1984 . Multidimensional capillary gas chromatography—Enantiomeric separations of selected cuts using a chiral second column . J. High Resolut. Chromatogr. Chromatogr. Commun. , 7 : 404 – 410 .
  • Mosandl , A. , Hener , U. , Hagenauer‐Hener , U. and Kustermann , A. 1989 . Stereoisomeric flavor compounds. XXXII: Direct enantiomer separation of chiral γ‐lactones from food and beverages by multidimensional gas chromatography . J. High Resolut. Chromatogr. , 12 : 532 – 536 .
  • Nitz , S. , Kollmannsberger , H. and Drawert , F. 1989 . Determination of non natural flavours in sparkling fruit wines. 1. Rapid method for the resolution of enantiomeric 7‐lactones by multidimensional GC . Chem. Mikrobiol. Technol. Lebensm. , 12 : 75 – 80 .
  • Bernreuther , A. , Christoph , N. and Schreier , P. 1989 . Determination of the enantiomeric composition of γ‐lactones in complex natural matrices using multidimensional capillary gas chromatography . J. Chromatogr. , 481 : 363 – 367 .
  • Guichard , E. , Kustermann , A. and Mosandl , A. 1990 . Chiral flavour compounds from apricots — distribution of γ‐lactone enantiomers and Stereodifferentiation of dihydroactinidiolide using multidimensional gas chromatography . J. Chromatogr. , 498 : 396 – 401 .
  • Mosandl , A. and Schubert , V. 1990 . Stereoisomere Aromastoffe. XXXIX: Chirale Inhaltsstoffe ätherischer Öle I. Stereodifferenzierung des Linalylacetas—ein neuer Weg zur Qualitätsbeurteilung des Lavendelöls . Z. Lebensm. Unters. Forsch. , 190 : 506 – 510 .
  • Kreis , P. , Hener , U. and Mosandl , A. 1990 . Chirale Inhaltsstoffe ätherischer Öle III: Stereodifferenzierung von a‐Pinen, 0‐Pinen und Limonen in ätherischen Ölen, Drogen und Fertigarzneimitteln . Dtsch. Apoth. Ztg. , 130 : 985 – 988 .
  • Hener , U. , Kreis , P. and Mosandl , A. 1990 . Chiral compounds of essential oils. IV. Enantiomer distribution of a‐pinene, β‐pinene and limonene in essential oils and extracts; Part 2: Perfumes and cosmetics . Flav. Fragr. J. , 5 : 201 – 204 .
  • Hener , U. , Kreis , P. and Mosandl , A. 1991 . Enantiomer distribution of a‐pinene, β‐pinene and limonene in essential oils and extracts; Part 3: Oils for alcoholic beverages and seasonings . Flav. Fragr. J. , 6 : 109 – 111 .
  • Palm , U. , Askari , C. , Hener , U. , Jakob , E. , Mandler , C. , Geßner , M. , Mosandl , A. , König , W. A. , Evers , P. and Krebber , R. 1991 . Stereoisomere Aromastoffe. XLVII: Direkte chirospezifische HRGC‐Analyse natürlicher δ‐Lactone . Z. Lebensm. Unters. Forsch. , 192 : 209 – 213 .
  • Kreis , P. , Hener , U. and Mosandl , A. 1991 . Chirale Inhaltsstoffe ätherischer Öle. V: Enantiomer‐enverteilung von a‐Pinen, β‐Pinen und Limonen in ätherischen Ölen und Extrakten; Citrus‐früchte und citrushaltige Getränke . Dtsch. Lebensm. Rundsch. , 87 : 8 – 11 .
  • Mosandl , A. , Fischer , K. , Hener , U. , Kreis , P. , Rettinger , K. , Schubert , V. and Schmarr , H.‐G. 1991 . Stereoisomeric flavor compounds. XLVIII. Chirospecific analysis of natural flavors and essential oils, using multidimensional gas chromatography . J. Agric. Food Chem. , 39 : 1131 – 1134 .
  • Mosandl , A. , Rettinger , K. , Weber , B. and Henn , D. 1990 . Untersuchungen zur Enantiomeren‐verteilung von 2‐Methylbuttersäure in Früchten und anderen Lebensmitteln mittels multi‐dimensionaler Gaschromatographie (MDGC) . Dtsch. Lebensm. Rundsch. , 86 : 375 – 379 .
  • Hollnagel , A. , Menzel , E.‐M. and Mosandl , A. 1991 . Chiral aroma compounds of sherry. II. Direct enantiomer separation of solerone and solerole . Z. Lebensm. Unters. Forsch. , 193 : 234 – 236 .
  • Schubert , V. , Diener , R. and Mosandl , A. 1991 . Enantioselective multidimensional gas chromatography of some secondary alcohols and their acetates from banana . Z. f. Naturforsch. , 46c : 33 – 36 .
  • Lehmann , D. , Askari , C. , Henn , D. , Dettmar , F. , Hener , U. and Mosandl , A. 1991 . Simultane Stereodifferenzierung chiraler γ‐ und δ‐Lactone . Dtsch. Lebensm. Rundsch. , 87 : 75 – 77 .
  • Askari , C. , Hener , U. , Schmarr , H.‐G. , Rapp , A. and Mosandl , A. 1991 . Stereodifferentiation of some chiral monoterpenes, using multidimensional gas chromatography . Fresenius J. Anal. Chem. , 340 : 768 – 772 .
  • Schubert , V. and Mosandl , A. 1991 . Stereoisomeric Flavour Compounds. LIII: Chiral compounds of essential oils. VIII; Stereodifferentiation of linalool using multidimensional gas chromatography . Phytochem. Anal. , 2 : 171 – 174 .
  • Karl , V. , Schmarr , H.‐G. and Mosandl , A. 1991 . Simultaneous stereoanalysis of 2‐alkylbranched acids, ‐esters, and ‐alcohols, using selectivity adjusted column system in multidimensional gas chromatography . J. Chromatogr. , 557 : 347 – 350 .
  • Bernreuther , A. , Koziet , J. , Brunerie , P. , Krammer , G. , Christoph , N. and Schreier , P. 1990 . Chirospecific capillary gas chromatography (HRGC) and on‐line HRGC‐isotope ratio mass spec‐trometry of 7‐decalactone from various sources . Z. Lebensm. Unters. Forsch. , 191 : 299 – 301 .
  • Bernreuther , A. , Lander , V. , Huffer , M. and Schreier , P. 1990 . Enantioselective analysis of dec‐2‐en‐5‐olide (massoilactone) from natural sources by multidimensional capillary gas chromatography . Flav. Fragr. J. , 5 : 71 – 73 .
  • Guichard , E. , Mosandl , A. , Hollnagel , A. , Latrasse , A. and Henry , R. 1991 . Chiral γ‐lactones from Fusarium poae: Enantiomeric ratios and sensory differentiation of cis‐6‐ γ‐dodecenolactone enantiomers . Z. Lebensm. Unters. Forsch. , 193 : 26 – 31 .
  • Mosandl , A. , Hener , U. , Kreis , P. and Schmarr , H.‐G. 1990 . Chiral compounds of essential oils. II. Enantiomer distribution of α‐pinene, β‐pinene and limonene in essential oils and extracts; Part 1, Rutaceae and gramineae . Flav. Fragr. J. , 5 : 193 – 199 .
  • Rettinger , K. , Karl , V. , Schmarr , H.‐G. , Dettmar , E. , Hener , U. and Mosandl , A. 1991 . Chirospecific analysis of 2‐alkylbranched alcohols, ‐acids, and ‐esters; chirality evaluation of 2‐methyl‐butanoates from apples and pineapples . Phytochem. Anal. , 2 : 184 – 188 .
  • Haase‐Aschoff , K. , Haase‐Aschoff , I. and Laub , H. 1991 . Chirale Analyse und Bewertung der 2‐Methylbuttersäure und ihrer Ester in Früchten und Fruchtprodukten . Lebensmittelchemie , 45 : 107 – 109 .
  • Full , G. , Bernreuther , A. , Krammer , G. and Schreier , P. 1991 . On‐line‐HRGC‐FTIR zur direkten Enantiodifferenzierung von Aromastoffen aus komplexen Matrices 30 – 34 . Labo
  • Hener , U. and Mosandl , A. 1993 . Zur Herkunftsbeurteilung von Aromen . Dtsch. Lebensm. Rundsch. , 89 : 307 – 312 .
  • Maarse , H. and Visscher , C. A. 1989 . “Volatile Compounds in Foods—Qualitative and Quantitative Data” , 6th ed. , Vols. 1–3 , Zeist : TNO‐C1VO Food Analysis Institute .
  • Mosandl , A. 1988 . Chirality in flavor chemistry—recent developments in synthesis and analysis . Food Rev. Int. , 4 : 1 – 43 .
  • Frank , H. , Nicholson , G. J. and Bayer , E. 1977 . Rapid gas Chromatographie separation of amino acid enantiomers with a novel chiral stationary phase . J. Chromatogr. Sci. , 15 : 174 – 176 .
  • König , W. A. , Benecke , I. and Sievers , S. 1981 . New results in the gaschromatographic separation of enantiomers of hydroxy acids and carbohydrates . J. Chromatogr. , 217 : 71 – 79 .
  • Schurig , V. and Bürkle , W. 1982 . Extending the scope of enantiomer resolution by complexation gas chromatography . J. Am. Chem. Soc. , 104 : 7573 – 7580 .
  • Juvancz , Z. , Alexander , G. and Szejtli , J. 1987 . Permethylated β‐cyclodextrin as stationary phase in capillary gas chromatography . J. High Resolut. Chromatogr. Chromatogr. Commun. , 10 : 105 – 107 .
  • Armstrong , D. W. , Chang , C.‐D. and Li , W. Y. 1990 . Relevance of enantiomeric separations in food and beverage analyses . J. Agric. Food Chem. , 38 : 1674 – 1677 .
  • Schurig , V. and Nowotny , H.‐P. 1988 . Separation of enantiomers on diluted permethylated ß‐cyclodextrin by high resolution gas chromatography . J. Chromatogr. , 441 : 155 – 163 .
  • Nowotny , H.‐P. , Schmalzing , D. , Wistuba , D. and Schurig , V. 1989 . Extending the scope of enantiomer separation on diluted methylated β‐cyclodextrin derivatives by high resolution gas chromatography . J. High Resolut. Chromatogr. , 12 : 383 – 393 .
  • Schurig , V. and Nowotny , H.‐P. 1990 . Gaschromatographische Enantiomerentrennung an Cyclo‐dextrinderivaten . Angew. Chem. , 102 : 969 – 986 .
  • Bruche , G. , Schmarr , H.‐G. , Bauer , A. , Mosandl , A. , Rapp , A. and Engel , L. 1991 . Stereoisomere Aromastoffe. LI: Stereodifferenzierung chiraler Furanone—Möglichkeiten und Grenzen der herkunftsspezifischen Aromastoff‐Analyse . Z. Lebensm. Unters. Forsch. , 193 : 115 – 118 .
  • Schmarr , H.‐G. , Mosandl , A. and Kaunzinger , A. 1991 . Influence of derivatization on the chiral selectivity of cyclodextrins: Alkylated/acylated cyclodextrins and γ/δ‐lactones as an example . J. Microcol. Sep. , 3 : 395 – 492 .
  • Schmarr , H.‐G. , Mosandl , A. , Neukom , H.‐P. and Grob , K. 1991 . Modified cyclodextrins as stationary phases for capillary GC; consequences of dilution in polysiloxanes . J. High Resolut. Chromatogr. , 14 : 207 – 210 .
  • Dietrich , A. , Maas , B. , Karl , V. , Kreis , P. , Lehmann , D. , Weber , B. and Mosandl , A. 1992 . Stereo‐siomeric flavor compounds, Part LV: Stereodifferentiation of some chiral volatiles on hep‐takis (2,3‐di‐O‐acetyl‐6‐O‐tert‐butyl‐dimethylsilyl)‐β‐cyclodextrin . J. High Resolut. Chromatogr. , 15 : 176 – 179 .
  • Cabrera , K. and Schwinn , G. 1989 . Cyclodextrine als chirale Selektoren für die Enantiomerentrennung in der HPLC (Teil 1): Dynamische Belegung von RP‐Phasen . Kontakte (Darmstadt) , : 3 – 8 .
  • Dietrich , A. , Maas , B. , Brand , G. , Karl , V. , Kaunzinger , A. and Mosandl , A. 1992 . Stereoisomeric flavor compounds, Part LX. Diluted modified cyclodextrins as chiral stationary phases‐the influence of the polysiloxane solvent . J. High Resolut. Chromatogr. , 75 : 769 – 772 .
  • Dietrich , A. , Maas , B. , Messer , W. , Bruche , G. , Karl , V. , Kaunzinger , A. and Mosandl , A. 1992 . Stereoisomeric flavor compounds, Part LVIII: The use of heptakis (2,3‐di‐O‐methyl‐6‐O‐tert‐butyldimethylsiIyl)‐β‐cycIodextrin as a chiral stationary phase in flavor analysis . J. High Resolut. Chromatogr. , 15 : 590 – 593 .
  • Maas , B. , Dietrich , A. , Bartschat , B. and Mosandl , A. 1995 . tert‐butyl‐Dimethylsilylated cyclodextrins—versatile chiral stationary phases in capillary gas chromatography . J. Chromatogr. Sci. , 33 : 223 – 228 .
  • Dietrich , A. , Maas , B. and Mosandl , A. 1994 . Diluted modified cyclodextrins as chiral cGC phases, the influence of the polysiloxane solvents to the enantioselectivity and column efficiency . J. Microcol. Sep. , 6 : 33 – 42 .
  • Werkhoff , P. , Brennecke , S. and Bretschneider , W. 1991 . Fortschritte bei der chirospezifischen Analyse natürlicher Riech‐ und Aromastoffe . Chem. Mikrobiol. Technol. Lebensm. , 13 : 129 – 152 .
  • Güntert , M. , Emberger , R. , Hopp , R. , Köpsel , M. , Silberzahn , W. and Werkhoff , P. 1991 . Chiro‐specific analysis in flavor and essential oil chemistry Part A. Filbertone—the character impact compound of hazel‐nuts . Z. Lebensm. Unters. Forsch. , 192 : 108 – 110 .
  • Werkhoff , P. , Bretschneider , W. , Güntert , M. , Hopp , R. and Surburg , H. 1991 . Chirospecific analysis in flavor and essential oil chemistry. Part B. Direct enantiomer resolution of trans‐a‐ionone and trans‐α‐damascone by inclusion gas chromatography . Z. Lebensm. Unters. Forsch. , 192 : 111 – 115 .
  • Winter , M. , Furrer , A. , Willhalm , B. and Thommen , W. 1976 . Identification and synthesis of two new organic sulfur compounds from the yellow passion fruit (Passiflora edulis f. flavi‐carpa) . Helv. Chim. Acta , 59 : 1613 – 1620 .
  • Singer , G. , Heusinger , G. , Fröhlich , O. , Schreier , P. and Mosandl , A. 1986 . Chirality evaluation of 2‐methyl‐4‐propyl‐l,3‐oxathiane from the yellow passion fruit . J. Agric. Food Chem. , 34 : 1029 – 1033 .
  • Weber , B. , Maas , B. and Mosandl , A. in press . Stereoisomeric flavor compounds. LXXII: Stereo‐isomeric distribution of some chiral sulfur containing trace components of yellow passion fruits . J. Agric. Food Chem. ,
  • Demole , E. , Enggist , P. and Ohloff , G. 1982 . l‐p‐Menthene‐8‐thiol: A powerful flavor impact constituent of grapefruit juice (Citrus paradisi Macfayden) . Helv. Chim. Acta , 65 : 1785 – 1794 .
  • Lehmann , D. , Dietrich , A. , Hener , U. and Mosandl , A. in press . Stereoisomeric flavour compounds. LXX. l‐p‐Menthene‐8‐thiol: Separation and sensory evaluation of the enantiomers by enan‐tioselective gas chromatography/olfactometry . Phytochem. Anal. ,
  • Maga , J. A. 1976 . Lactones in Foods . Crit. Rev. Food Sci. Nutrit. , 8 : 1 – 56 .
  • Albrecht , W. and Tressl , R. 1990 . Studies on the biosynthesis of ‐γ‐decalactone in Sporobolomyces odorus . Z. Naturforsch. , 45c : 207 – 216 .
  • Guichard , E. and Souty , M. 1988 . Comparison of the relative quantities of aroma compounds found in fresh apricot (Prunus armeniaca) from six different varieties . Z. Lebensm. Unters. Forsch. , 186 : 301 – 307 .
  • Grosch , W. 1990 . Analyse von Aromastoffen . Chem. Unserer Zeit , 24 : 82 – 89 .
  • Blank , I. and Grosch , W. 1991 . Evaluation of potent odorants in dill seed and dill herb (Anethum graveolens L.) by aroma extract dilution analysis . J. Food Sci. , 56 : 63 – 67 .
  • Siek , T. J. , Albin , J. A. , Sather , L. A. and Lindsay , R. C. 1971 . Comparison of flavor thresholds of aliphatic lactones with those of fatty acids, esters, aldehydes, alcohols and ketones . J. Dairy Sci. , 54 : 1 – 4 .
  • Leffingwell , J. G. and Leffingwell , D. 1991 . GRAS flavor chemicals—detection threshold . Per‐fum. Flavourist , 16 : 1 – 19 .
  • Fischer , N. and Hammerschmidt , F. J. 1992 . A contribution to the analysis of fresh strawberry flavour . Chem. Mikrobiol. Technol. Lebensm. , 14 : 141 – 148 .
  • Nitz , S. , Kollmannsberger , H. , Weinreich , B. and Drawert , F. 1991 . Enantiomeric distribution and 13C/12C isotope ratio determination of γ‐lactones: Appropriate methods for the differentiation between natural and non‐natural flavours? . J. Chromatogr. , 557 : 187 – 197 .
  • Eberhardt , R. , Woidich , H. and Pfannhauser , H. 1981 . “ Analysis of natural and artificial coconut flavouring in beverages ” . In “Flavour ‘81” , Edited by: Schreier , P. 377 – 383 . Berlin : de Gruyter .
  • König , W. A. , Krebber , R. and Mischnick , P. 1989 . Cyclodextrins as chiral stationary phases in capillary gas chromatography. Part V: Octakis (3‐O‐butyryl‐2,6‐di‐O‐pentyl)‐γ‐cyclodex‐trin . J. High Resolut. Chromatogr. , 12 : 732 – 738 .
  • Lehmann , D. , Dietrich , A. , Schmidt , S. , Dietrich , H. and Mosandl , A. 1993 . Stereodifferenzie‐rung von γ(δ) Lactonen and (E)‐α‐lonon verschiedener Früchte und ihrer Verarbeitungsprodukte . Z. Lebensm. Unters. Forsch. , 196 : 207 – 213 .
  • Nitz , S. and Kollmannsberger , H. 1993 . Changes in flavor composition during the thermal concentration of apricot puree . Z. Lebensm. Unters. Forsch. , 197 : 541 – 545 .
  • Maas , B. , Dietrich , A. , Karl , V. , Kaunzinger , A. , Lehmann , D. , Köpke , T. and Mosandl , A. 1993 . tert‐Butyldimethylsilyl‐substituted cyclodextrin derivatives as versatile chiral stationary phases in capillary GC . J. Microcol. Sep. , 5 : 421 – 427 .
  • Lehmann , D. , Maas , B. and Mosandl , A. 1995 . Stereoisomeric flavour compounds. LXIX: Ster‐eodifferentiation of the δ(γ)‐lactones C8‐C18 in dairy products, margarine, and coconut . Z. Lebensm. Unters. Forsch. , 201 : 55 – 61 .
  • Rettinger , K. , Burschka , C. , Scheeben , P. , Fuchs , H. and Mosandl , A. 1991 . Chiral 2‐alkyl‐branched acids, esters and alcohols. Preparation and stereospecific flavour evaluation . Tetrahedron Asymm. , 2 : 965 – 968 .
  • Karl , V. , Dietrich , A. and Mosandl , A. 1993 . Stereoisomeric flavour compounds. LXIV: The chirospecific analysis of 2‐alkyl‐branched flavour compounds from headspace extracts and their sensory evaluation . Phytochem. Anal. , 4 : 158 – 164 .
  • Karl , V. 1994 . Chirale Aromastoffe—Alkylverzweigte Säuren, Ester und Alkohole; Analyse und Reindarstellung der Enantiomeren , University of Frankfurt/M. . Dissertation
  • Marner , O. A. , Tjoa , S.S. , Sriver , Ch. R. and Klassen , G. A. 1976 . Demonstration of a new mammalian isoleucine catabolic pathway yielding an (R)‐series of metabolites . Biochem. J. , 160 : 417 – 426 . and literature cited therein
  • Rettinger , K. , Weber , B. and Mosandl , A. 1990 . Stereoisomere Aromastoffe. XLII: 2‐Methyl‐buttersäure‐Enantiomerenverteilung in Äpfeln und apfelhaltigen Lebensmitteln . Z. Lebensm. Unters. Forsch. , 191 : 265 – 268 .
  • Bicchi , C. and Pisciotta , A. 1990 . Use of two‐dimensional gas chromatography in the direct enan‐tiomer separation of chiral essential oil components . J. Chromatogr. , 508 : 341 – 348 .
  • Askari , C. , Kreis , P. , Mosandl , A. and Schmarr , H.‐G. 1992 . Chiral compounds of essential oils. VII: Quality evaluation of Mentha oils, using enantioselective CGC analysis of monoter‐penoid constituents . Arch. Pharm. , 325 : 35 – 39 .
  • Faber , B. , Dietrich , A. and Mosandl , A. 1994 . Chiral compounds of essential oils. Part XV. Ster‐eodifferentiation of characteristic compounds of Mentha species by multi‐dimensional gas chromatography . J. Chromatogr. , 666 : 161 – 165 .
  • Kreis , P. , Dietrich , A. , Juchelka , D. and Mosandl , A. 1993 . Methodenvergleich zur Stereodifferenzierung von Linalool und Linalylacetat in ätherischen Ölen von Lavandula angusti‐folia Miller . Pharm. Ztg. Wiss. , 138 : 149 – 155 .
  • Cotroneo , A. , Stagno d'AIcontres , I. and Trozzi , A. 1992 . On the genuineness of citrus essential oils. Part XXXIV. Detection of added reconstituted bergamot oil in genuine bergamot essential oil by high resolution gaschromatography with chiral capillary columns . Flavour Fragr. J. , 7 : 15 – 17 .
  • Dugo , G. , Stagno d'AIcontres , I. , Cotroneo , A. and Dugo , P. On the genuineness of citrus essential oils. Part XXXV. Detection of added reconstituted mandarin oil in genuine cold‐pressed mandarin essential oil by high resolution gas chromatography with chiral capillary columns . J. Essent. Oil Res. , 4 589 – 594 . (1992) Part XXXVI
  • 1993 . Detection of added reconstituted lemon oil in genuine cold‐pressed lemon essential oil by high resolution gas chromatography with chiral capillary columns . J. Essent. Oil Res. , 5 : 21 – 26 .
  • Kreis , P. , Braunsdorf , R. , Dietrich , A. , Hener , U. , Maas , B. and Mosandl , A. 1993 . “ Enantioselective analysis of linalol—scope and limitations ” . In “Progress in Flavour Precursor Studies, Analysis, Generation, Biotechnology” , Edited by: Schreier , P. and Winterhalter , P. 77 – 82 . Allured Publ. Corp. .
  • Derbesy , M. and Uzio , R. 1993 . Application of chiral phase chromatography to coriander essential oil control . Ann. Falsif. Expert. Chim. Toxicol. , 56 (923) : 369 – 378 .
  • Sundt , E. , Willhalm , B. , Chappaz , R. and Ohloff , G. 1971 . Das organoleptische Prinzip von Cassis‐Flavor im Buchublätteröl . Helv. Chim. Acta , 54 : 1801 – 1805 .
  • Lamparsky , D. and Schudel , P. 1971 . p‐Menthane‐8‐thiol‐3‐one, a new component of Buchu leaf oil . Tetrahedron Lett. , 36 : 3323 – 3326 .
  • Köpke , T. and Mosandl , A. 1992 . Stereoisomere Aromastoffe. LIV. 8‐Mercapto‐p‐menthan‐3‐on, Reindarstellung und chirospezifische Analyse der Stereoisomeren . Z. Lebensm. Unters. Forsch. , 194 : 372 – 376 .
  • Köpke , T. , Dietrich , A. and Mosandl , A. 1994 . Chiral compounds of essential oils. XIV: Simultaneous stereoanalysis of Buchu leaf oil compounds . Phytochem. Anal. , 5 : 61 – 67 .
  • Mosandl , A. , Köpke , T. and Bensch , W. 1993 . Stereoisomeric Flavour compounds. LXII. Structure elucidation of 8‐mercapto‐p‐menthan‐3‐one isomers . Tetrahedron Asymm. , 4 : 651 – 654 .
  • Mosandl , A. , Bruche , G. , Askari , C. and Schmarr , H.‐G. 1990 . Stereoisomeric flavor compounds. XLIV: Enantioselective analysis of some important flavor molecules . J. High Resolut. Chromatogr. , 13 : 660 – 662 .
  • Barrie , A. , Bricout , J. and Koziet , J. 1984 . Gas chromatography —Stable isotope ratio analysis at natural abundance levels . Biomed. Mass Spectrom. , 11 : 583 – 588 .
  • Rautenschlein , M. , Habfast , K. and Brand , W. 1990 . “ High‐precision measurement of 13C/12C ratios by on‐line combustion of GC eluates and isotope ratio mass spectrometry ” . In “Stable Isotopes in Paediatric, Nutritional and Metabolic Research” , Edited by: Chapman , T. E. , Berger , R. , Reyngoud , D. J. and Okken , A. 133 – 148 . Hampshire, , U.K. : Intercept, Andover .
  • Mosandl , A. , Braunsdorf , R. , Bruche , G. , Dietrich , A. , Hener , U. , Karl , V. , Köpke , T. , Kreis , P. , Lehmann , D. and Maas , B. 1995 . New methods to assess authenticity of natural flavors and essential oils . ACS Symp. Ser. , 596 : 94 – 112 .
  • Hener , U. , Braunsdorf , R. , Kreis , P. , Dietrich , A. , Maas , B. , Euler , E. , Schlag , B. and Mosandl , A. 1992 . Chiral compounds of essential oils. X: The role of linalool in the origin evaluation of essential oils . Chem. Mikrobiol. Technol. Lebensm. , 14 : 129 – 133 .
  • Braunsdorf , R. , Hener , U. , Lehmann , D. and Mosandl , A. 1991 . Analytische Differenzierung zwischen natürlich gewachsenen, fermentativ erzeugten und synthetischen (naturidentischen) Aromastoffen. I: Herkunftsspezifische Analyse des (E)‐α(β)‐Ionons . Dtsch. Lebensm. Rundsch. , 87 : 277 – 280 .
  • Maas , B. , Dietrich , A. and Mosandl , A. 1993 . Enantioselective capillary gaschromatography‐olfactometry in essential oil analysis . Naturwiss. , 80 : 470 – 472 .
  • Weber , B. , Dietrich , A. , Maas , B. , Marx , A. , Olk , J. and Mosandl , A. 1994 . Stereoisomeric flavour compounds. LXVI: Enantiomeric distribution of the chiral sulfur‐containing alcohols in yellow and purple passion fruits . Z. Lebensm. Unters. Forsch. , 199 : 48 – 50 .
  • Kreis , P. and Mosandl , A. 1992 . Chiral compounds of essential oils. XI: Simultaneous stereo‐analysis of Lavandula oil constituents . Flavour Fragr. J. , 7 : 187 – 193 .
  • Braunsdorf , R. , Hener , U. , Przibilla , G. , Piecha , S. and Mosandl , A. 1993 . Analytische und technologische Einflüsse auf das 13C/12C‐Isotopenverhältnis von Orangenöl‐Komponenten . Z. Lebensm. Unters. Forsch. , 197 : 24 – 28 .
  • Braunsdorf , R. , Hener , U. , Stein , S. and Mosandl , A. 1993 . Comprehensive cGC‐IRMS analysis in the authenticity control of flavours and essential oils. Part I: Lemon Oil . Z. Lebensm. Unters. Forsch. , 197 : 137 – 141 .
  • Braunsdorf , R. 1994 . Herkunftsspezifische Aromastoffanalytik mittels Isotopenmassenspektro‐metrie , Universität Frankfurt/M. . Dissertation
  • Lehmann , D. 1994 . Neue Ergebnisse zur herkunftsspezifischen Aromastoffanalyse , Universität Frankfurt/M. . Dissertation
  • Werkhoff , P. , Brennecke , S. , Bretschneider , W. , Güntert , M. , Hopp , R. and Surburg , H. 1993 . Chirospecific analysis in essential oil, fragrance and flavor research . Z. Lebensm. Unters. Forsch. , 196 : 307 – 328 .
  • Aeree , T. E. , Nishida , R. and Fukami , H. 1985 . Odor thresholds of the stereoisomers of methyl jasmonate . J. Agric. Food Chem. , 33 : 425 – 427 .
  • Guichard , E. , Hollnagel , A. , Mosandl , A. and Schmarr , H.‐G. 1990 . Stereoisomeric flavor compounds. Part XL: Stereodifferentiation of some chiral volatiles on a permethylated ß‐cyclodextrin phase . J. High Resolut. Chromatogr. , 13 : 299 – 301 .
  • Full , G. , Winterhalter , P. , Schmidt , G. , Herion , P. and Schreier , P. 1993 . MDGG‐MS: A powerful tool for enantioselective flavor analysis . J. High Resolut. Chromatogr. , 16 : 642 – 644 .
  • Herion , P. , Full , G. , Winterhalter , P. and Schreier , P. 1993 . Enaritiodifferentiation of isomeric vitispiranes . Phytochem. Anal. , 4 : 235 – 239 .
  • Bartschat , D. , Lehmann , D. , Dietrich , A. , Mosandl , A. and Kaiser , R. 1995 . Chiral compounds of essential oils. XIX: 4‐Methyl‐5‐decanolide: Chirospecific analysis, structure and properties of the stereoisomers . Phytochem. Anal. , 6 : 130 – 134 .
  • Nitz , S. , Weinreich , B. and Drawert , F. 1992 . Multidimensional gas chromatography‐isotope ratio mass spectrometry (MDGC‐IRMS). Part Á: System description and technical requirements . J. High Resolut. Chromatogr. , 15 : 387 – 391 .
  • Braunsdorf , R. , Hener , U. and Mosandl , A. 1992 . Analytische Differenzierung zwischen natürlich gewachsenen, fermentativ erzeugten und synthetischen (naturidentischen) Aromastoffen: Mitt. II: GC‐C‐IRMS Analyse aromarelevanter Aldehyde—Grundlagen und Anwendungsbeispiele . Z. Lebensm. Unters. Forsch. , 194 : 426 – 430 .
  • Hener , U. , Faulhaber , S. , Kreis , P. and Mosandl , A. 1995 . On the authenticity evaluation of balm oil (Melissa officinals L.) . Pharmazie , 50 : 60 – 62 .
  • Karl , V. , Gutser , J. , Dietrich , A. , Maas , B. and Mosandl , A. 1994 . Stereoisomeric flavour compounds. LXVIII. 2‐, 3‐, and 4‐Alkyl‐branched acids, Part 2: Chirospecific analysis and sensory evaluation . Chirality , 6 : 427 – 434 .
  • Kreis , P. and Mosandl , A. 1992 . Chiral compounds of essential oils. XII: Authenticity control of rose oils, using enantioselective multidimensional gas chromatography . Flavour Fragr J. , 7 : 199 – 203 .
  • Kreis , P. , Dietrich , A. and Mosandl , A. 1994 . Chiral compounds of essential oils. XVIII: On the authenticity assessment of essential oil of Rosmarinus officinalis L. . Pharmazie , 49 : 761 – 765 .
  • Kreis , P. and Mosandl , A. 1994 . Chiral compounds of essential oils. XVI: Enantioselective multidimensional gas chromatography in authenticity control of balm oil . Flavour Fragr. J. , 9 : 249 – 256 .
  • Kreis , P. and Mosandl , A. 1994 . Chiral compounds of essential oils. XVII: Simultaneous stereo‐analysis of Cymbopogon oil constituents . Flavour Fragr. J. , 9 : 257 – 260 .
  • Schumacher , K. , Turgeon , H. and Mosandl , A. 1995 . Sample preparation for gas chromatography‐isotope ratio mass spectrometry, an investigation with volatile components from strawberries . Phytochem. Anal. , 6 in press
  • Faber , B. , Krause , B. , Dietrich , A. and Mosandl , A. 1995 . Gas chromatography‐isotope ratio mass spectrometry in the analysis of peppermint oil and its importance in the authenticity control . J. Essent. Oil Res. , 7 : 123 – 131 .
  • Karl , V. , Dietrich , A. and Mosandl , A. 1994 . Gas chromatography‐isotope ratio mass spectrometry measurements of some carboxylic esters from different apple varieties . Phytochem. Anal., J. , : 32 – 37 .
  • Bruche , G. , Dietrich , A. and Mosandl , A. 1995 . Stereoisomeric flavour compounds. LXXI: Determination of the origin of aroma‐active dihydrofuranones . Z. Lebensm. Unters. Forsch. , 201 : 249 – 252 .

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