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 GlossaryTermGC
. 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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
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
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)
R. Rienacker, G. Ohloff: Optisch aktives β-citronellol aus (\(+\))- oder (-)- Pinan, Angew. Chem. 73, 240 (1961)
E. Brenna, C. Fuganti, S. Serra: Enantioselective perception of chiral odorants, Tetrahedron. Asymmetry 14, 1–42 (2003)
E. Gil-Av: Present status of enantiomeric analysis by gas chromatography, J. Mol. Evol. 6, 131–144 (1975)
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)
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)
Z. Juvancz, P. Petersson: Enantioselective gas chromatography, J. Microcolumn Sep. 8, 99–114 (1996)
W.A. Konig: Enantioselective gas-chromatography, Trends Anal. Chem. 12, 130–137 (1993)
P. Schreier, A. Bernreuther, M. Huffer: Analysis of Chiral Organic Molecules (Walter de Gruyter, Berlin 1995)
E. Bayer: Chirale Erkennung von Naturstoffen an optisch aktiven Polysiloxanen, Z. Naturforsch. 38b, 1281–1291 (1983)
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)
H. Frank, G.J. Nicholson, E. Bayer: Chiral polysiloxanes for resolution of optical antipodes, Angew. Chem. Int. Ed. Engl. 17, 363–365 (1978)
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)
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)
V. Schurig, W. Burkle: Extending the scope of enantiomer resolution by complexation gas chromatography, J. Am. Chem. Soc. 104, 7573–7580 (1982)
V. Schurig, H.P. Nowotny: Separation of enantiomers on diluted permethylated β-Cyclodextrin by high-resolution gas chromatography, J. Chromatogr. 441, 155–163 (1988)
V. Schurig: Enantiomer separation by gas-chromatography on chiral stationary phases, J. Chromatogr. A 666, 111–129 (1994)
V. Schurig: Separation of enantiomers by gas chromatography, J. Chromatogr. A 906, 275–299 (2001)
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)
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)
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)
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)
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)
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)
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)
V. Schurig: Chirodichroism of different enantiomeric compositions of a planar d\({}^{8}\)-metal complex, Angew. Chem. Int. Ed. Engl. 20, 807–808 (1981)
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)
P. Schreier: Bioflavour ’87 (Walter de Gruiter, Berlin 1988)
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)
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)
A. Villiers: Sur la fermentation de la fécule par l’action du ferment butyrique, C. R. Acad. Sci. 112, 536 (1891)
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)
H. Pringsheim: Chemistry of the Saccarides (McGraw-Hill, New York 1932)
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)
D. French: The Schardinger dextrins, Adv. Carbohydr. Chem. 12, 189–260 (1957)
F. Cramer: Einschlussverbindungen (Inclusion Compounds) (Springer-Verlag, Berlin 1954)
J. Szejtli: Introduction and general overview of cyclodextrin chemistry, Chem. Rev. 98, 1743–1753 (1998)
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)
Z. Juvancz, G. Alexander, J. Szejtli: Permethylated β-Cyclodextrin as stationary phase in capillary gas chromatography, J. High Resolut. Chromatogr. 10, 105–107 (1987)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
A. Venema, H. Henderiks, R. Vongeest: The enantioselectivity of modified cyclodextrins – studies on interaction mechanisms, J. High Resolut. Chromatogr. 14, 676–680 (1991)
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)
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)
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)
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)
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)
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)
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)
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)
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)
E. Gil-Av, J. Herling: Determination of the stability constants of complexes by gas chromatography, J. Phys. Chem. 66, 1208–1209 (1962)
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)
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)
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)
V. Schurig: Terms for the quantitation of a mixture of stereoisomers, Enantiomer 1, 139–143 (1996)
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)
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)
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)
W.A. Konig: Enantioselective capillary gas chromatography in the investigation of stereochemical correlations of terpenoids, Chirality 10, 499–504 (1998)
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)
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)
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)
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)
E. Kovats: Gas-chromarographische Charakteriserung organischer Verbindungen. Retention-indices aliphatischer Halogenide, alkohole, aldehyde und ketone, Helv. Chim. Acta 41, 1915–1932 (1958)
H. Van den Dool: Standardisation of gas chromatographic analysis of essential oils, Ph.D. Thesis (University of Groeningen, Groeningen 1974)
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)
L.M. Blumberg, M.S. Klee: Method translation and retention time locking in partition GC, Anal. Chem. 70, 3828–3839 (1998)
V. Giarrocco, B. Quimby, M. Klee: Retention Time Locking: Concepts and Application Gas Chromatography Application Note (Agilent Technologies, Wilmington 1997)
D.R. Deans: A new technique for heart-cutting in gas chromatography, Chromatographia 1, 18–21 (1968)
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)
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)
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)
R. Shellie, P.J. Marriott: Comprehensive two-dimensional gas chromatography with fast enantioseparation, Anal. Chem. 74, 5426–5430 (2002)
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)
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)
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)
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.)
NIST: NIST/EPA/NIH Mass Spectral Library (National Institute of Standards and Technology, Gaithersburg, MD 2005)
FFNSC 2.0: Flavors and fragrances of natural and synthetic compounds – Mass spectral database (Chromaleont, Messina 2007)
R.P. Adams: Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry (Allured, Carol Stream Illinois 2007)
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)
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)
A.V. Asten: The importance of GC and GC-MS in perfume analysis, Trends Anal. Chem. 21, 698–708 (2002)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
H. Grosenick, V. Schurig, J. Costante, A. Collet: Gas-chromatographic enantiomer separation of bromochlorofluoromethane, Tetrahedron Asymmetry 6, 87–88 (1995)
M. Lindstrom: Improved enantiomer separation using very short capillary columns coated with permethylated beta-cyclodextrin, J. High Resolut. Chromatogr. 14, 765–767 (1991)
V. Schurig, H. Czesla: Miniaturization of enantioselective gas chromatography, Enantiomer 6, 107–128 (2001)
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)
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)
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)
P. Kreiss, A. Mosandl: Chiral compounds of essential oils. Part XI. Simultaneous stereoanalysis of Lavandula oil costituents, Flavour Fragr. J. 7, 187–193 (1992)
L.M. Blumberg: Theory of fast capillary gas chromatography part 2: Speed of analysis, J. High Resolut. Chromatogr. 20, 679–687 (1997)
L.M. Blumberg: Theory of fast capillary gas chromatography. 1. Column efficiency, J. High Resolut. Chromatogr. 20, 597–604 (1997)
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)
L.M. Blumberg, M.S. Klee: Optimal heating rate in gas chromatography, J. Microcolumn Sep. 12, 508–514 (2000)
M.S. Klee, L.M. Blumberg: Theoretical and practical aspects of fast gas chromatography and method translation, J. Chromatogr. Sci. 40, 234–247 (2002)
GC Method Translation Software: www.chem.agilent.com (accessed June 2016)
P.S. Dittrich, K. Tachikawa, A. Manz: Micro total analysis systems. Latest advancements and trends, Anal. Chem. 78, 3887–3907 (2006)
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)
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)
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)
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)
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)
E. Baltussen, C.A. Cramers, P.J.F. Sandra: Sorptive sample preparation a review, Anal. Bioanal. Chem. 373, 3–22 (2002)
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
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
Download citation
DOI: https://doi.org/10.1007/978-3-319-26932-0_19
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-26930-6
Online ISBN: 978-3-319-26932-0
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)