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Enantioselective Gas Chromatography with Cyclodextrin in Odorant Analysis

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Springer Handbook of Odor

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Abstract

This chapter concerns enantioselective gas-chromatography (GlossaryTerm

Es-GC

) with cyclodextrin derivatives as chiral stationary phases for chiral recognition of volatile odorants in the flavor and fragrance field. The text is divided into two main parts. The first one is more general and deals with enantiomers and odor and need for chiral recognition, evolution of chiral stationary phases for Es-GC since its beginning, followed by the history of cyclodextrins and their applications to enantioselective GlossaryTerm

GC

. It also includes some theoretical aspects of enantiomer separation with cyclodextrin derivatives and their influence on routine chiral recognition.

The second part concerns the strategy of chiral recognition in routine analysis with cyclodextrin derivatives as chiral stationary phases illustrated by examples with real natural product samples. This part describes enantiomer automatic identification or their excess or ratio determination in complex mixtures by enantioselective GC combined with mass spectrometry; in particular it deals with the potential of multidimensional techniques and of fast GC in chiral recognition and the role played by mass spectrometry. The last paragraph concerns the use of total analysis systems in chiral recognition.

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Abbreviations

CD:

cyclodextrin

ee:

enantiomeric excess

er:

enantiomeric ratio

Es-GC:

enantioselective gas chromatography

FID:

flame ionization detection

GC:

gas chromatography

HCC-HS:

high concentration capacity headspace

HPLC:

high performance liquid chromatography

HS-LPME:

headspace liquid-phase microextraction

HS-SPME:

headspace solid-phase microextraction

HS-STE:

headspace sorptive tape extraction

HS:

headspace

HSSE:

headspace sorptive extraction

IRMS:

isotope ratio mass spectrometry

IT:

ion trap

MS:

mass spectrometry

PDMS:

polydimethylsiloxane

RIA:

retention index allowance

RTL:

retention time locking

S-HS:

static headspace

TOF:

time-of-flight

UV–Vis:

ultraviolet-visible

References

  1. B. Koppenhoefer, R. Behnisch, U. Epperlein, H. Holzschuh, A. Bernreuther, P. Piras, C. Roussel: Enantiomeric odor differences and gas chromatographic properties of flavors and fragrances, Perfume Flavorist 19, 1–14 (1994)

    CAS  Google Scholar 

  2. R. Rienacker, G. Ohloff: Optisch aktives β-citronellol aus (\(+\))- oder (-)- Pinan, Angew. Chem. 73, 240 (1961)

    Article  CAS  Google Scholar 

  3. E. Brenna, C. Fuganti, S. Serra: Enantioselective perception of chiral odorants, Tetrahedron. Asymmetry 14, 1–42 (2003)

    Article  CAS  Google Scholar 

  4. E. Gil-Av: Present status of enantiomeric analysis by gas chromatography, J. Mol. Evol. 6, 131–144 (1975)

    Article  CAS  Google Scholar 

  5. E. Gil-Av, B. Feibush: Resolution of enantiomers by gas-liquid chromatography with an optical active stationary phase: Separation on packed columns, Tetrahedron Lett. 8(35), 3345–3347 (1967)

    Article  Google Scholar 

  6. E. Gil-Av, B. Feibush, R. Charles-Sigler: Separation of enantiomers by gas-liquid chromatography with an optical active stationary phase, Tetrahedron Lett. 7(10), 1009–1015 (1966)

    Article  Google Scholar 

  7. Z. Juvancz, P. Petersson: Enantioselective gas chromatography, J. Microcolumn Sep. 8, 99–114 (1996)

    Article  CAS  Google Scholar 

  8. W.A. Konig: Enantioselective gas-chromatography, Trends Anal. Chem. 12, 130–137 (1993)

    Article  Google Scholar 

  9. P. Schreier, A. Bernreuther, M. Huffer: Analysis of Chiral Organic Molecules (Walter de Gruyter, Berlin 1995)

    Book  Google Scholar 

  10. E. Bayer: Chirale Erkennung von Naturstoffen an optisch aktiven Polysiloxanen, Z. Naturforsch. 38b, 1281–1291 (1983)

    CAS  Google Scholar 

  11. H. Frank, G.J. Nicholson, E. Bayer: Rapid gas chromatographic separation of amino acid enantiomers with a novel chiral stationary phase, J. Chromatogr. Sci. 15, 174–176 (1977)

    Article  CAS  Google Scholar 

  12. H. Frank, G.J. Nicholson, E. Bayer: Chiral polysiloxanes for resolution of optical antipodes, Angew. Chem. Int. Ed. Engl. 17, 363–365 (1978)

    Article  Google Scholar 

  13. V. Schurig: Gas chromatographic separation of enantiomers on optically active metal-complex-free stationary phases. New analytical methods, Angew. Chem. Int. Ed. Engl. 23, 747–765 (1984)

    Article  Google Scholar 

  14. V. Schurig, M. Juza, M. Preschel, G.J. Nicholson, E. Bayer: Gas-chromatographic enantiomer separation of proteinogenic amino acid derivatives: Comparison of Chirasil-val and Chirasil-gamma-dex used as chiral stationary phases, Enantiomer 4, 297–303 (1999)

    CAS  Google Scholar 

  15. V. Schurig, W. Burkle: Extending the scope of enantiomer resolution by complexation gas chromatography, J. Am. Chem. Soc. 104, 7573–7580 (1982)

    Article  CAS  Google Scholar 

  16. V. Schurig, H.P. Nowotny: Separation of enantiomers on diluted permethylated β-Cyclodextrin by high-resolution gas chromatography, J. Chromatogr. 441, 155–163 (1988)

    Article  CAS  Google Scholar 

  17. V. Schurig: Enantiomer separation by gas-chromatography on chiral stationary phases, J. Chromatogr. A 666, 111–129 (1994)

    Article  CAS  Google Scholar 

  18. V. Schurig: Separation of enantiomers by gas chromatography, J. Chromatogr. A 906, 275–299 (2001)

    Article  CAS  Google Scholar 

  19. B. Feibush: Interaction between asymmetric solutes and solvents. N-Lauroyl-L-valyl-t-butylamide as stationary phase in gas liquid partition chromatography, J. Chem. Soc. Chem. Commun. 11, 544–545 (1971)

    Article  Google Scholar 

  20. W.A. Konig, I. Benecke, H. Bretting: Gas chromatographic separation of carbohydrate enantiomers on anew chiral stationary phase, Angew. Chem. Int. Ed. Engl. 20, 693–694 (1981)

    Article  Google Scholar 

  21. B. Koppenhoefer, U. Muhleck, K. Lohmiller: Backbone modification of chirasil-Val – Effect of nonpolar side-chains on enantiomer separation in gas-chromatography, Chromatographia 40, 718–723 (1995)

    Article  CAS  Google Scholar 

  22. B. Koppenhoefer, U. Muhleck, K. Lohmiller: Backbone modification of chirasil-val. 1. Effect of loading on the separation of enantiomers by gas-chromatography, J. Chromatogr. A 699, 215–221 (1995)

    Article  CAS  Google Scholar 

  23. B. Koppenhoefer, U. Muhleck, M. Walser, K. Lohmiller: Backbone modification of chirasil-val. 2. Introduction of a rigid cyclohexyl spacer, J. Chromatogr. Sci. 33, 217–222 (1995)

    Article  CAS  Google Scholar 

  24. J. Pfeiffer, V. Schurig: Enantiomer separation of amino acid derivatives on a new polymeric chiral resorc[4]arene stationary phase by capillary gas chromatography, J. Chromatogr. A 840, 145–150 (1999)

    Article  CAS  Google Scholar 

  25. V. Schurig: Resolution of a chiral olefin by complexation chromatography on an optically active rhodium(I) complex, Angew. Chem. Int. Ed. Engl. 16, 110 (1977)

    Article  Google Scholar 

  26. V. Schurig: Chirodichroism of different enantiomeric compositions of a planar d\({}^{8}\)-metal complex, Angew. Chem. Int. Ed. Engl. 20, 807–808 (1981)

    Article  Google Scholar 

  27. V. Schurig, D. Schmalzing, M. Schleimer: Enantiomer separation on immobilized Chirasil-Metal and Chirasil-Dex by gas-chromatography and supercritical fluid chromatography, Angew. Chem. Int. Ed. Engl. 30, 987–989 (1991)

    Article  Google Scholar 

  28. P. Schreier: Bioflavour ’87 (Walter de Gruiter, Berlin 1988)

    Google Scholar 

  29. C. Bicchi, A. Pisciotta: Use of 2-dimensional gas-chromatography in the direct enantiomer separation of chiral essential oil components, J. Chromatogr. 508, 341–348 (1990)

    Article  CAS  Google Scholar 

  30. D. Wistuba, O. Trager, V. Schurig: Enantio- and regioselectivity in the epoxide-hydrolase-catalyzed ring opening of simple aliphatic oxiranes: Part II: Dialkyl- and trialkylsubstituted oxiranes, Chirality 4, 185 (1992)

    Article  CAS  Google Scholar 

  31. A. Villiers: Sur la fermentation de la fécule par l’action du ferment butyrique, C. R. Acad. Sci. 112, 536 (1891)

    Google Scholar 

  32. F. Schardinger: Über thermophile Bakterien aus verschiedenen Speisen und Milch, sowie über einige Umsetzungsprodukte derselben in kohlenhydrathaltigen Nährlösungen, darunter krystallisierte Polysaccharide (Dextrine) aus Stärke, Z. Unters. Nahr. Genussm. 6, 865–880 (1903)

    Article  CAS  Google Scholar 

  33. H. Pringsheim: Chemistry of the Saccarides (McGraw-Hill, New York 1932)

    Google Scholar 

  34. K. Freudenberg, G. Blomquist, L. Ewald, K. Soff: Hydrolyse und Acetolyse der Stärke und der Schardinger-Dextrine, Ber. Dtsch. Chem. Ges. 69, 1258–1966 (1936)

    Article  Google Scholar 

  35. D. French: The Schardinger dextrins, Adv. Carbohydr. Chem. 12, 189–260 (1957)

    CAS  Google Scholar 

  36. F. Cramer: Einschlussverbindungen (Inclusion Compounds) (Springer-Verlag, Berlin 1954)

    Book  Google Scholar 

  37. J. Szejtli: Introduction and general overview of cyclodextrin chemistry, Chem. Rev. 98, 1743–1753 (1998)

    Article  CAS  Google Scholar 

  38. T. Koscielski, D. Sybilska, J. Jurczak: Separation of α-and β-pinene into enantiomers in gas-liquid chromatography systems via α-cyclodextrin inclusion complexes, J. Chromatogr. 280, 131–134 (1983)

    Article  CAS  Google Scholar 

  39. Z. Juvancz, G. Alexander, J. Szejtli: Permethylated β-Cyclodextrin as stationary phase in capillary gas chromatography, J. High Resolut. Chromatogr. 10, 105–107 (1987)

    Article  CAS  Google Scholar 

  40. G. Alexander, Z. Juvancz, J. Szejtli: Cyclodextrins and their derivatives as stationary phases in GC capillary columns, J. High Resolut. Chromatogr. Chromatogr. Commun. 11, 110–113 (1988)

    Article  CAS  Google Scholar 

  41. A. Venema, P.J.A. Tolsma: Enantiomer separation with capillary gas-chromatography columns coated with cyclodextrins. 1. Separation of enantiomeric 2-substituted propionic-acid esters and some lower alcohols with permethylated beta-cyclodextrin, J. High Resolut. Chromatogr. 12, 32–34 (1989)

    Article  CAS  Google Scholar 

  42. W.A. Konig, R. Krebber, G. Wenz: Enantioselective capillary gas-chromatography on the basis of host-guest interactions with modified cyclodextrins, J. High Resolut. Chromatogr. 12, 641–644 (1989)

    Article  Google Scholar 

  43. W.A. Konig, S. Lutz, P. Mischnickübbecke, B. Brassat, G. Wenz: Cyclodextrins as chiral stationary phases in capillary gas-chromatography. 1. Pentylated alpha-cyclodextrin, J. Chromatogr. 447, 193–197 (1988)

    Article  Google Scholar 

  44. W.A. Konig, S. Lutz, G. Wenz: Modified cyclodextrins – novel, highly enantioselective stationary phases for gas-chromatography, Angew. Chem. Int. Ed. Engl. 27, 979–980 (1988)

    Article  Google Scholar 

  45. W.A. Konig, S. Lutz, G. Wenz, E. Vonderbey: Cyclodextrins as chiral stationary phases in capillary gas-chromatography. 2. Heptakis(3-O-acetyl-2,6-di-O-pentyl)-beta-cyclodextrin, J. High Resolut. Chromatogr. Chromatogr. Commun. 11, 506–509 (1988)

    Article  Google Scholar 

  46. V. Schurig, M. Jung, D. Schmalzing, M. Schleimer, J. Duvekot, J.C. Buyten, J.A. Peene, P. Mussche: CGC enantiomer separation on diluted cyclodextrin derivatives coated on fused-silica columns, J. High Resolut. Chromatogr. 13, 470–474 (1990)

    Article  CAS  Google Scholar 

  47. C. Bicchi, G. Artuffo, A. D’Amato, V. Manzin, A. Galli, M. Galli: Cyclodextrin derivatives in the GC separation of racemic mixtures of volatile compounds Part VI: The influence of the diluting phase on the enantioselectivity of 2,6-di-O-methyl-3-O-pentyl-β-cyclodextrin, J. High Resolut. Chromatogr. 16, 209–214 (1993)

    Article  CAS  Google Scholar 

  48. C. Bicchi, A. D’Amato, V. Manzin, A. Galli, M. Galli: Cyclodextrin derivatives in GC separation of racemic mixtures of volatiles. 9. The influence of the different polysiloxanes as diluting phase for 2,3-di-O-acetyl-6-O-t-butyldimethylsilyl-beta-cyclodextrin on the separation of some racemates, J. Microcolumn Sep. 7, 327–336 (1995)

    Article  CAS  Google Scholar 

  49. W. Blum, R. Aichholz: Gas-Chromatographic enantiomer separation on tert-butyldimethylsilylated beta-cyclodextrin diluted in PS-086 - a simple method to prepare enantioselective glass-capillary columns, J. High Resolut. Chromatogr. 13, 515–518 (1990)

    Article  CAS  Google Scholar 

  50. F. Kobor, K. Angermund, G. Schomburg: Molecular modeling experiments on chiral recognition in GC with specially derivatized cyclodextrins as selectors, J. High Resolut. Chromatogr. 16, 299–311 (1993)

    Article  CAS  Google Scholar 

  51. A. Dietrich, B. Maas, V. Karl, P. Kreis, D. Lehmann, B. Weber, A. Mosandl: Stereoisomeric flavor compounds. 55. Stereodifferentiation of some chiral volatiles on heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin, J. High Resolut. Chromatogr. 15, 176–179 (1992)

    Article  CAS  Google Scholar 

  52. C. Bicchi, C. Cagliero, E. Liberto, B. Sgorbini, K. Martina, G. Cravotto, P. Rubiolo: New asymmetrical per-substituted cyclodextrins (2-O-methyl-3-O-ethyl- and 2-O-ethyl-3-O-methyl-6-O-t-butyldimethylsilyl-beta-derivatives) as chiral selectors for enantioselective gas chromatography in the flavour and fragrance field, J. Chromatogr. A 1217, 1106–1113 (2010)

    Article  CAS  Google Scholar 

  53. M. Bayer, A. Mosandl: Improved gas chromatographic stereodifferentiation of chiral main constituents from different essential oils using a mixture of chiral stationary phases, Flavour Fragr. J. 19, 515–517 (2004)

    Article  CAS  Google Scholar 

  54. M.Y. Nie, L.M. Zhou, Q.H. Wang, D.Q. Zhu: Gas chromatographic enantiomer separation on single and mixed cyclodextrin derivative chiral stationary phases, Chromatographia 51, 736–740 (2000)

    Article  CAS  Google Scholar 

  55. X.Y. Shi, Y.Q. Zhang, R.N. Fu: Synergistic effects of mixed GC stationary phase consisting of two different cyclodextrin derivatives, Anal. Chim. Acta 424, 271–277 (2000)

    Article  CAS  Google Scholar 

  56. S. Tamogami, K. Awano, M. Amaike, Y. Takagi, T. Kitahara: Development of an efficient GLC system with a mixed chiral stationary phase and its application to the separation of optical isomers, Flavour Fragr. J. 16, 349–352 (2001)

    Article  CAS  Google Scholar 

  57. P.A. Levkin, A. Ruderisch, V. Schurig: Combining the enantioselectivity of a cyclodextrin and a diamide selector in a mixed binary gas-chromatographic chiral stationary phase, Chirality 18, 49–63 (2006)

    Article  CAS  Google Scholar 

  58. P.A. Levkin, A. Levkina, V. Schurig: Combining the enantioselectivities of L-valine diamide and permethylated beta-cyclodextrin in one gas chromatographic chiral stationary phase, Anal. Chem. 78, 5143–5148 (2006)

    Article  CAS  Google Scholar 

  59. O. Stephany, F. Dron, S. Tisse, A. Martinez, J.-M. Nuzillard, V. Peulon-Agasse, P. Cardinaël, J.-P. Bouillon: (L)- or (D)-Valine tert-butylamide grafted on permethylated β-cyclodextrin derivatives as new mixed binary chiral selectors: Versatile tools for capillary gas chromatographic enantioseparation, J. Chromatogr. A 1216, 4051–4062 (2009)

    Article  CAS  Google Scholar 

  60. O. Stephany, S. Tisse, G. Coadou, J.P. Bouillon, V. Peulon-Agasse, P. Cardinael: Influence of amino acid moiety accessibility on the chiral recognition of cyclodextrin-amino acid mixed selectors in enantioselective gas chromatography, J. Chromatogr. A 1270, 254–261 (2012)

    Article  CAS  Google Scholar 

  61. V. Schurig, Z. Juvancz, G.J. Nicholson, D. Schmalzing: Separation of enantiomers on immobilized polysiloxane-anchored permethyl-beta-cyclodextrin (chirasil-dex) by supercritical fluid chromatography, J. High Resolut. Chromatogr. 14, 58–62 (1991)

    Article  CAS  Google Scholar 

  62. J. Donnecke, C. Paul, W.A. Konig, L.A. Svensson, O. Gyllenhaal, J. Vessman: Immobilization of heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-beta-cyclodextrin for capillary gas chromatography and supercritical fluid chromatography and micro-liquid chromatography, J. Microcolumn Sep. 8, 495–505 (1996)

    Article  CAS  Google Scholar 

  63. D.W. Armstrong, Y.B. Tang, T. Ward, M. Nichols: Derivatized cyclodextrins immobilized on fused-silica capillaries for enantiomeric separations via capillary electrophoresis, gas-chromatography, or supercritical fluid chromatography, Anal. Chem. 65, 1114–1117 (1993)

    Article  CAS  Google Scholar 

  64. V. Schurig, H.P. Nowotny: Gas-Chromatographic separation of enantiomers on optically-active metal-complex-free stationary phases. 2. Gas-Chromatographic separation of enantiomers on cyclodextrin derivatives, Angew. Chem. Int. Ed. Engl. 29, 939–957 (1990)

    Article  Google Scholar 

  65. A. Venema, H. Henderiks, R. Vongeest: The enantioselectivity of modified cyclodextrins – studies on interaction mechanisms, J. High Resolut. Chromatogr. 14, 676–680 (1991)

    Article  CAS  Google Scholar 

  66. A. Berthod, W.Y. Li, D.W. Armstrong: Multiple enantioselective retention mechanisms on derivatized cyclodextrin gas-chromatographic chiral stationary phases, Anal. Chem. 64, 873–879 (1992)

    Article  CAS  Google Scholar 

  67. K.B. Lipkowitz, B. Coner, M.A. Peterson, A. Morreale: Enantioselective binding in gas chromatography: A computational study of chiral selection by permethyl-beta-cyclodextrin, J. Phys. Org. Chem. 10, 311–322 (1997)

    Article  CAS  Google Scholar 

  68. K.B. Lipkowitz, R. Coner, M.A. Peterson: Locating regions of maximum chiral discrimination: A computational study of enantioselection on a popular chiral stationary phase used in chromatography, J. Am. Chem. Soc. 119, 11269–11276 (1997)

    Article  CAS  Google Scholar 

  69. K.B. Lipkowitz, R. Coner, M.A. Peterson, A. Morreale, J. Shackelford: The principle of maximum chiral discrimination: Chiral recognition in permethyl-beta-cyclodextrin, J. Org. Chem. 63, 732–745 (1998)

    Article  CAS  Google Scholar 

  70. V. Schurig, H.P. Nowotny, M. Schleimer, D. Schmalzing: Gas-chromatographic enantiomer separation on per-N-pentylated amylose, J. High Resolut. Chromatogr. 12, 549–551 (1989)

    Article  CAS  Google Scholar 

  71. G. Sicoli, Z. Jiang, L. Jicsinsky, V. Schurig: Modified linear dextrins (acyclodextrins) as new chiral selectors for the gas-chromatographic separation of enantiomers, Angew. Chem. Int. Ed. Engl. 44, 4092 (2005)

    Article  CAS  Google Scholar 

  72. G. Sicoli, F. Pertici, Z. Jiang, L. Jicsinsky, V. Schurig: Gas-chromatographic approach to probe the absence of molecular inclusion in enantioseparations by carbohydrates. Investigation of linear dextrins (acyclodextrins) as novel chiral stationary phases, Chirality 19, 391–400 (2007)

    Article  CAS  Google Scholar 

  73. A. Mosandl, K. Rettinger, K. Fischer, V. Schubert, H.G. Schmarr, B. Maas: Stereoisomeric flavor compounds-Xli–New applications of permethylated beta-cyclodextrin phase in chiral cgc analysis, J. High Resolut. Chromatogr. 13, 382–385 (1990)

    Article  CAS  Google Scholar 

  74. M. Jung, D. Schmalzing, V. Schurig: Theoretical approach to the gas-chromatographic separation of enantiomers on dissolved cyclodextrin derivatives, J. Chromatogr. 552, 43–57 (1991)

    Article  CAS  Google Scholar 

  75. E. Gil-Av, J. Herling: Determination of the stability constants of complexes by gas chromatography, J. Phys. Chem. 66, 1208–1209 (1962)

    Article  CAS  Google Scholar 

  76. M.A. Muhs, F.T. Weiss: Determination of equilibrium constants of silver-olefin complexes using gas chromatography, J. Am. Chem. Soc. 84, 4697–4705 (1962)

    Article  CAS  Google Scholar 

  77. V. Schurig, R.C. Chang, A. Zlatkis, B. Feibush: Thermodynamics of molecular association by gas-liquid chromatography. s-Donor molecules and dimeric 3-trifluoroacetylcamphorates of Mn(II), Co(II) and Ni(II), J. Chromatogr. 99, 147 (1974)

    Article  CAS  Google Scholar 

  78. U. Beitler, B. Feibush: Interaction between asymmetric solutes and solvents: Diamides derived from l-valine as stationary phases in gas-liquid partition chromatography, J. Chromatogr. 123, 149–176 (1976)

    Article  CAS  Google Scholar 

  79. V. Schurig: Terms for the quantitation of a mixture of stereoisomers, Enantiomer 1, 139–143 (1996)

    CAS  Google Scholar 

  80. L. Mondello, D. Sciarrone, R. Costa, G. Dugo: The chiral compounds of Citrus oils. In: Citrus Oils, Composition, Advanced Analytical Techniques, Contaminants and Biological Activity, ed. by G. Dugo, L. Mondello (CRC Press, Boca Raton 2011)

    Google Scholar 

  81. C. Cagliero, C. Bicchi, C. Cordero, P. Rubiolo, B. Sgorbini, E. Liberto: Fast headspace-enantioselective GC-mass spectrometric-multivariate statistical method for routine authentication of flavoured fruit foods, Food Chem. 132, 1071–1079 (2012)

    Article  CAS  Google Scholar 

  82. M. Heil, F. Podebrad, T. Beck, A. Mosandl, A.C. Sewell, H. Bohles: Enantioselective multidimensional gas chromatography mass spectrometry in the analysis of urinary organic acids, J. Chromatogr. B 714, 119–126 (1998)

    Article  CAS  Google Scholar 

  83. W.A. Konig: Enantioselective capillary gas chromatography in the investigation of stereochemical correlations of terpenoids, Chirality 10, 499–504 (1998)

    Article  CAS  Google Scholar 

  84. M. Heidt, U. Bornscheuer, R.D. Schmid: Studies on the enantioselectivity in the lipase-catalyzed synthesis of monoacylglycerols from isopropylidene glycerol, Biotechnol. Tech. 10, 25–30 (1996)

    Article  CAS  Google Scholar 

  85. W. Vetter, V. Schurig: Enantioselective determination of chiral organochlorine compounds in biota by gas chromatography on modified cyclodextrins, J. Chromatogr. A 774, 143–175 (1997)

    Article  CAS  Google Scholar 

  86. W. Vetter, U. Klobes, K. Hummert, B. Luckas: Gas chromatographic separation of chiral organochlorines on modified cyclodextrin phases and results of marine biota samples, J. High Resolut. Chromatogr. 20, 85–93 (1997)

    Article  CAS  Google Scholar 

  87. M. Schneider, K. Ballschmiter: Alkyl nitrates as achiral and chiral solute probes in gas chromatography - Novel properties of a beta-cyclodextrin derivative and characterization of its enantioselective forces, J. Chromatogr. A 852, 525–534 (1999)

    Article  CAS  Google Scholar 

  88. E. Kovats: Gas-chromarographische Charakteriserung organischer Verbindungen. Retention-indices aliphatischer Halogenide, alkohole, aldehyde und ketone, Helv. Chim. Acta 41, 1915–1932 (1958)

    Article  CAS  Google Scholar 

  89. H. Van den Dool: Standardisation of gas chromatographic analysis of essential oils, Ph.D. Thesis (University of Groeningen, Groeningen 1974)

    Google Scholar 

  90. H. Van den Dool, P.D. Kratz: A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography, J. Chromatogr. A 11, 463–471 (1963)

    Article  Google Scholar 

  91. L.M. Blumberg, M.S. Klee: Method translation and retention time locking in partition GC, Anal. Chem. 70, 3828–3839 (1998)

    Article  CAS  Google Scholar 

  92. V. Giarrocco, B. Quimby, M. Klee: Retention Time Locking: Concepts and Application Gas Chromatography Application Note (Agilent Technologies, Wilmington 1997)

    Google Scholar 

  93. D.R. Deans: A new technique for heart-cutting in gas chromatography, Chromatographia 1, 18–21 (1968)

    Article  Google Scholar 

  94. L. Mondello, M. Catalfamo, C. Dugo, P. Dugo: Multidimensional tandem capillary gas chromatography system for the analysis of real complex samples. Part I: Development of a fully automated tandem gas chromatography system, J. Chromatogr. Sci. 36, 201–209 (1998)

    Article  CAS  Google Scholar 

  95. G. Schomburg, H. Husmanm, E. Hubinger, W.A. Konig: Multidimensional capillary gas chromatography - Enantiomeric separation of selected cuts using a chiral second column, J. High Resolut. Chromatogr. 7, 404–410 (1984)

    Article  CAS  Google Scholar 

  96. Z.Y. Liu, J.B. Phillips: Comprehensive 2-dimensional gas-chromatography using an on-column thermal modulator interface, J. Chromatogr. Sci. 29, 227–231 (1991)

    Article  CAS  Google Scholar 

  97. R. Shellie, P.J. Marriott: Comprehensive two-dimensional gas chromatography with fast enantioseparation, Anal. Chem. 74, 5426–5430 (2002)

    Article  CAS  Google Scholar 

  98. R. Shellie, L. Mondello, G. Dugo, P. Marriott: Enantioselective gas chromatographic analysis of monoterpenes in essential oils of the family Myrtaceae, Flavour Fragr. J. 19, 582–585 (2004)

    Article  CAS  Google Scholar 

  99. B. d’Acampora Zellner, C. Bicchi, P. Dugo, P. Rubiolo, G. Dugo, L. Mondello: Linear retention indices in gas chromatographic analysis: A review, Flavour Fragr. J. 23, 297–314 (2008)

    Google Scholar 

  100. P. Rubiolo, B. Sgorbini, E. Liberto, C. Cordero, C. Bicchi: Analysis of the plant volatile fraction. In: The Chemistry and Biology of Volatiles, ed. by A. Herrmann (Wiley, Chichester 2010)

    Google Scholar 

  101. AMDIS (2007) National Institute of Standards and Technology AMDIS, http://chemdata.nist.gov/dokuwik/doku.php?id=chemdata:amdis, Version 2.65. (last accessed March 2014.)

  102. NIST: NIST/EPA/NIH Mass Spectral Library (National Institute of Standards and Technology, Gaithersburg, MD 2005)

    Google Scholar 

  103. FFNSC 2.0: Flavors and fragrances of natural and synthetic compounds – Mass spectral database (Chromaleont, Messina 2007)

    Google Scholar 

  104. R.P. Adams: Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry (Allured, Carol Stream Illinois 2007)

    Google Scholar 

  105. L. Mondello, P. Dugo, A. Basile, G. Dugo, K.D. Bartle: Interactive use of Linear Retention Indices, on polar and apolar columns, with a MS-library for reliable identification of complex mixtures, J. Microcolumn Sep. 7, 581–591 (1995)

    Article  CAS  Google Scholar 

  106. R. Shellie, P. Marriott, G. Zappia, L. Mondello, G. Dugo: Interactive use of linear retention indices on polar and apolar columns with an MS-library for reliable characterization of Australian tea tree and other Melaleuca sp oils, J. Essential Oil Res. 15, 305–312 (2003)

    Article  CAS  Google Scholar 

  107. A.V. Asten: The importance of GC and GC-MS in perfume analysis, Trends Anal. Chem. 21, 698–708 (2002)

    Article  Google Scholar 

  108. E. Liberto, C. Cagliero, B. Sgorbini, C. Bicchi, D. Sciarrone: B. d’Acampora Zellner, L. Mondello, P. Rubiolo: Enantiomer identification in the flavour and fragrance fields by ‘‘interactive’’ combination of linear retention indices from enantio selective gas chromatography and mass spectrometry, J. Chromatogr. A 1195, 117–126 (2008)

    Article  CAS  Google Scholar 

  109. R. Costa, M.R. De Fina, M.R. Valentino, P. Dugo, L. Mondello: Reliable identification of terpenoids and related compounds by using linear retention indices interactively with mass spectrometry search, Nat. Product Commun. 2, 413–418 (2007)

    CAS  Google Scholar 

  110. C. Bicchi, G. Artuffo, A. Damato, V. Manzin, A. Galli, M. Galli: Cyclodextrin derivatives in the Gc separation of racemic mixtures of volatile compounds. 5. Heptakis 2,6-dimethyl-3-pentyl-beta-cyclodextrins, J. High Resolut. Chromatogr. 15, 710–714 (1992)

    Article  CAS  Google Scholar 

  111. W.A. Konig, B. Gehrcke, D. Icheln, P. Evers, J. Donnecke, W.C. Wang: New, selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils, J. High Resolut. Chromatogr. 15, 367–372 (1992)

    Article  Google Scholar 

  112. B. Maas, A. Dietrich, D. Bartschat, A. Mosandl: Tert-butyldimethylsilylated cyclodextrins – versatile chiral stationary phases in capillary gas-chromatography, J. Chromatogr. Sci. 33, 223–228 (1995)

    Article  CAS  Google Scholar 

  113. C. Bicchi, A. DAmato, V. Manzin, A. Galli, M. Galli: Cyclodextrin derivatives in the gas chromatographic separation of racemic mixtures of volatile compounds. 10. 2,3-di-O-ethyl-6-O-tert-butyldimethylsilyl-beta- and -gamma-cyclodextrins, J. Chromatogr. A 742, 161–173 (1996)

    Article  CAS  Google Scholar 

  114. A. Mosandl: Enantioselective capillary gas chromatography and stable isotope ratio mass spectrometry in the authenticity control of flavrs and essential oils, Food Rev. Int. 11, 597–664 (1995)

    Article  CAS  Google Scholar 

  115. P. Rubiolo, E. Liberto, B. Sgorbini, R. Russo, J.L. Veuthey, C. Bicchi: Fast-GC-conventional quadrupole mass spectrometry in essential oil analysis, J. Sep. Sci. 31, 1074–1084 (2008)

    Article  CAS  Google Scholar 

  116. I. Hardt, W.A. Konig: Diluted versus undiluted cyclodextrin derivatives in capillary gas-chromatography and the effect of linear carrier gas velocity, column temperature, and length on enantiomer separation, J. Microcolumn Sep. 5, 35–40 (1993)

    Article  CAS  Google Scholar 

  117. C. Bicchi, G. Artuffo, A. Damato, A. Galli, M. Galli: Cyclodextrin derivatives in Gc separation of racemic mixtures of volatiles. 3, Chirality 4, 125–131 (1992)

    Article  CAS  Google Scholar 

  118. H. Grosenick, V. Schurig, J. Costante, A. Collet: Gas-chromatographic enantiomer separation of bromochlorofluoromethane, Tetrahedron Asymmetry 6, 87–88 (1995)

    Article  CAS  Google Scholar 

  119. M. Lindstrom: Improved enantiomer separation using very short capillary columns coated with permethylated beta-cyclodextrin, J. High Resolut. Chromatogr. 14, 765–767 (1991)

    Article  CAS  Google Scholar 

  120. V. Schurig, H. Czesla: Miniaturization of enantioselective gas chromatography, Enantiomer 6, 107–128 (2001)

    CAS  Google Scholar 

  121. C. Bicchi, L. Blumberg, C. Cagliero, C. Cordero, P. Rubiolo, E. Liberto: Development of fast enantioselective gas-chromatographic analysis using gas-chromatographic method-translation software in routine essential oil analysis (lavender essential oil), J. Chromatogr. A 1217, 1530–1536 (2010)

    Article  CAS  Google Scholar 

  122. C. Bicchi, E. Liberto, C. Cagliero, C. Cordero, B. Sgorbini, P. Rubiolo: Conventional and narrow bore short capillary columns with cyclodextrin derivatives as chiral selectors to speed-up enantioselective gas chromatography and enantioselective gas chromatography-mass spectrometry analyses, J. Chromatogr. A 1212, 114–123 (2008)

    Article  CAS  Google Scholar 

  123. C. Bicchi, V. Manzin, A. D’Amato, P. Rubiolo: Cyclodextrin derivatives in GC separation of enantiomers of essential oil, aroma and flavour compounds, Flavour Fragr. J. 10, 127–137 (1995)

    Article  CAS  Google Scholar 

  124. P. Kreiss, A. Mosandl: Chiral compounds of essential oils. Part XI. Simultaneous stereoanalysis of Lavandula oil costituents, Flavour Fragr. J. 7, 187–193 (1992)

    Article  Google Scholar 

  125. L.M. Blumberg: Theory of fast capillary gas chromatography part 2: Speed of analysis, J. High Resolut. Chromatogr. 20, 679–687 (1997)

    Article  CAS  Google Scholar 

  126. L.M. Blumberg: Theory of fast capillary gas chromatography. 1. Column efficiency, J. High Resolut. Chromatogr. 20, 597–604 (1997)

    Article  CAS  Google Scholar 

  127. L.M. Blumberg: Theory of fast capillary gas chromatography - Part 3: Column performance vs. gas flow rate, J. High Resolut. Chromatogr. 22, 403–413 (1999)

    Article  CAS  Google Scholar 

  128. L.M. Blumberg, M.S. Klee: Optimal heating rate in gas chromatography, J. Microcolumn Sep. 12, 508–514 (2000)

    Article  CAS  Google Scholar 

  129. M.S. Klee, L.M. Blumberg: Theoretical and practical aspects of fast gas chromatography and method translation, J. Chromatogr. Sci. 40, 234–247 (2002)

    Article  CAS  Google Scholar 

  130. GC Method Translation Software: www.chem.agilent.com (accessed June 2016)

  131. P.S. Dittrich, K. Tachikawa, A. Manz: Micro total analysis systems. Latest advancements and trends, Anal. Chem. 78, 3887–3907 (2006)

    Article  CAS  Google Scholar 

  132. A. Manz, N. Graber, H.M. Widmer: Miniaturized total chemical-analysis systems – A novel concept for chemical sensing, Sens. Actuators B-Chem. 1, 244–248 (1990)

    Article  CAS  Google Scholar 

  133. C. Cagliero, B. Sgorbini, C. Cordero, E. Liberto, C. Bicchi, P. Rubiolo: Analytical strategies for multipurpose studies of a plant volatile fraction. In: Handbook of Chemical and Biological Plant Analytical Methods, ed. by K. Hostettmann, H. Stuppner, A. Marston, S. Chen (Wiley, Chichester 2014)

    Google Scholar 

  134. C. Bicchi, C. Cordero, E. Liberto, B. Sgorbini, P. Rubiolo: Headspace sampling in flavor and fragrance field. In: Comprehensive Sampling and Sample Preparation, ed. by J. Pawliszyn (Elsevier, Oxford 2012)

    Google Scholar 

  135. B. Sgorbini, C. Bicchi, C. Cagliero, C. Cordero, E. Liberto, P. Rubiolo: Headspace sampling and gas chromatography: A successful combination to study the composition of a plant volatile fraction. In: Handbook of Chemical and Biological Plant Analytical Methods, ed. by K. Hostettmann, H. Stuppner, A. Marston, S. Chen (Wiley, Chichester 2014)

    Google Scholar 

  136. C. Bicchi, C. Cordero, P. Rubiolo: A survey on high-concentration-capability headspace sampling techniques in the analysis of flavors and fragrances, J. Chromatogr. Sci. 42, 402–409 (2004)

    Article  CAS  Google Scholar 

  137. E. Baltussen, C.A. Cramers, P.J.F. Sandra: Sorptive sample preparation a review, Anal. Bioanal. Chem. 373, 3–22 (2002)

    Article  CAS  Google Scholar 

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Cagliero, C., Sgorbini, B., Cordero, C., Liberto, E., Rubiolo, P., Bicchi, C. (2017). Enantioselective Gas Chromatography with Cyclodextrin in Odorant Analysis. In: Buettner, A. (eds) Springer Handbook of Odor. Springer Handbooks. Springer, Cham. https://doi.org/10.1007/978-3-319-26932-0_19

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