Determination of the Enantiomeric Composition of Limonene and Limonene-1,2-epoxide in Lemon Peel by Multidimensional Gas Chromatography with Flame-Ionization Detection and Selected Ion Monitoring Mass Spectrometry

Journal of Chromatographic Science

Volumn 36, Issue 1, 1998, Pages 37-43

  Blanch, Gracia P ^a   Nicholson, Graeme J ^b  

^a INSTITUTO DE FERMENTACIONES INDUSTRIALES CSIC   (Spain)

^b UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CITRUS LIMON;

EID: 0041796283     PISSN: 00219665     EISSN: None     Source Type: Journal    
DOI: 10.1093/chromsci/36.1.37     Document Type: Article

References (37)

1. F. Drawert and N. Christoph. Analysis of Volatiles. P. Schreier, Ed. Berlin, Germany, 1984, pp. 269-91.
2. P.E. Shaw. Review of quantitative analyses of citrus essential oils. J. Agric. Food Chem. 27: 246-57 (1979).
3. T.S. Chamblee, B.C. Clark Jr., G.B. Brewster, T. Radford, and G.A. lacobucci. Quantitative analyses of the volatile constituents of lemon peel oil - Effects of silica gel chromatography on the composition of its hydrocarbon and oxygenated tractions. J. Agric. Food Chem. 39: 162-69 (1991).
4. M. Yajaira Combariza, C. Blanco Tirado, E. Stashenko, and T. Shibamoto. Limonene concentration in lemon (Citrus volkameriana) peel oil as a function of ripeness. J. High Res. Chromatogr. 17: 643-46 (1994).
5. C.B. Tirado, E.E. Stashenko, M.Y. Combariza, and J.R. Martiner. Comparative study of Colombian citrus oils by high-resolution gas chromatography and gas chromatography-mass spectrometry. J. Chromatogr. A. 697: 501-13 (1995).
6. R.L. Kanerva, G.M. Ridder, F.R. Lefever, and C.L. Alden. Comparison of short term renal effects due to oral administration of decalin or d-limonene in young adult male fischer-344 rats. Food Chem. Toxicol. 25: 345-54 (1987).
7. P.A. Rodriguez, R. Takigiku, L.D. Lehman-Mckeeman, M.L. Fey, C.L. Eddy, and D. Caudill. Design of a gas chromatograph with parallel radioactivity and mass spectrometric detection - Application to the identification of the major metabolite of d-limonene associated with α2u-globulin. J. Chromatogr. 563: 271-82 (1991).
8. L.D. Lehman-Mckeeman, P.A. Rodriguez, R. Takigiku, D. Caudill, and M.L. Fey. D-Limonene induced male rat specific nephrotoxicity-evaluation of the association between d-limonene and α2u-globulin. Toxicol. Appl. Pharmacol. 99: 250-259 (1989).
9. X.-J. Chen, A. Archelas, and R. Furstoss. Microbiological transformations, XXVII. The first examples for preparative-scale enantioselective or diastereoselective epoxide hydrolyses using microorganisms. An unequivocal access to all four bisabolol stereoisomers. J. Org. Chem. 58: 5528-32 (1993).
10. R. Croteau. Proceedings of the International Conference. P. Schreier and P. Winterhalter, Eds. Würzburg, Germany, 1992, pp. 113-22.
11. W. Bertsch. Methods in high resolution gas chromatography. Two-dimensional techniques. J. High Res. Chromatogr. Chromatogr. Commun. 1: 85-90 (1978).
12. C. Wang, H. Frank, G. Wang, L. Zhou, E. Bayer, and P. Lu. Determination of amino acid enantiomers by two column gas chromatography with valveless column switching. J. Chromatogr. 262: 352-59 (1983).
13. G. Schomburg, H. Husmann, E. Hübinger, and W.A. König. Multidimensional capillary gas-chromatography enantiomeric separations of selected cuts using a chiral second column. J. High Res. Chromatogr. Chromatogr. Commun. 7: 404-10 (1984).
14. C. Bicchi and A. Pisciotta. Use of two-dimensional gas-chromatography in the direct enantiomer separation of chiral essential oil components. J. Chromatogr. 508: 341-48 (1990).
15. A. Mosandl. Capillary gas-chromatography in quality assessment of flavors and fragances. J. Chromatogr. 624: 267-92 (1992).
16. B. Weber. B. Maas, and A. Mosandl. Stereoisomeric flavor compounds. LXXII. Stereoisomeric distribution of some chiral sulfur-containing trace components of yellow passion fruits. J. Agric. Food Chem. 43: 2438-41 (1995).
17. V. Schurig and H.P. Nowotny. Separation of enantiomers on diluted permethylated β-cyclodextrin by high-resolution gas chromatography. J. Chromatogr. 441: 155-63 (1988).
18. W.A. König. Gas Chromatographic Enantiomer Separation with Modified Cyclodextrins. Hüthig, Heidelberg, Germany, 1992.
19. K.A. Krock, N. Ragunathan, and C.L. Wilkins. Parallel cryogenic trapping multidimensional gas-chromatography with direct linked infrared and mass spectral detection. J. Chromatogr. 645: 153-59 (1993).
20. N. Ragunathan, K.A. Krock, and C.L. Wilkins. Multidimensional gas chromatography with parallel cryogenic traps. Anal. Chem. 65: 1012-16 (1993).
21. K.A. Krock and C.L. Wilkins. Quantitative aspects of a valve-based, multistage multidimensional gas chromatography infrared spectroscopy mass spectrometry system. J. Chromatogr. A. 678: 265-77 (1994).
22. O. Nishimura. Identification of the characteristic odorants in fresh rhizomes of Ginger (Zingiber - Officinate Roscoe) using aroma extract dilution analysis and modified multidimensional gas chromatography mass spectroscopy. J. Agric. Food Chem. 43: 2941-45 (1995).
23. B. Maas, A. Dietrich, D. Bartschat, and A. Mosandl. tert-Butyldimethylsilylated cyclodextrins: Versatile chiral stationary phases in capillary gas chromatography. J. Chromatogr. Sci. 33: 223-28 (1995).
24. X. Wang, C. Jia, and H. Wan. The direct chiral separation of some optically active compounds in essential oils by multidimensional gas chromatography. J. Chromatogr. Sci. 33: 22-25 (1995).
25. S.T. Likens and G.B. Nickerson. Detection of certain hop oil constituents in brewing products. Am. Soc. Brew. Chem. Proc. 5-13 (1964).
26. R.A. Flath and R.R. Forrey. Volatile components of papaya (Carica papaya L. Solo Variety). J. Agric. Food Chem. 25: 103-109 (1977).
27. M. Godefroot, P. Sandra, and M. Verzele. New method for quantitative essential oil analysis. J. Chromatogr. 203: 325-35 (1981).
28. G.P. Blanch, J. Tabera, M. Herraiz, and G. Reglero. Preconcentration of volatile components of foods. Optimization of the steam distillation solvent-extraction at normal pressure. J. Chromatogr. 628: 261-68 (1993).
29. V. Seidel and W. Lindner. Universal sample enrichment technique for organochlorine pesticides in environmental and biological samples using a redesigned simultaneous steam distillation solvent extraction apparatus. Anal. Chem. 65: 3677-83 (1993).
30. S. Mayer. Enantiomeranalytik mittels oberflächenfixierten und gelösten Cyclodextrin - Derivaten in der Kapillarelektrophorese. Doctoral thesis, University of Tübingen, Germany, 1993.
31. P. Schieberle and W. Grosch. Identification of potent flavor compounds formed in an aqueous lemon oil/citric acid emulsion. J. Agric. Food Chem. 36: 797-800 (1988).
32. H. Günther. Untersuchungen an Citronenölen mit Hilfe der Gaschromatographie und der Infrarotspektroskopie. Dtsch. Lebensm. Rundsch. 64: 104-11 (1968).
33. W.A. Bonner. Enantiomeric markers in the quantitative gas chromatographic analysis of optical isomers. Application to the estimation of amino acid degradation. J. Chromatogr. Sci. 11: 101-104 (1973).
34. P. Kreis, U. Hener, and A. Mosandl. Chiral compounds of essential oils. V. Enantiomeric distribution of α-pinene, β-pinene and limonene in essential oils and extracts-citrus fruits and citrus containing beverages. Dtsch. Lebens. Rundsch. 87: 8-11 (1991).
35. V. Schurig, M. Schleimer, M. Jung, S. Mayer, and A. Glausch. Proceedings of the International Conference. P. Schreier and P. Winterhalter, Eds. Würzburg, Germany, 1992, pp. 63-75.
36. L. Salles, C. Anbry, F. Rober, G. Chottard, R. Thowenor, H. Ledon, and J.-M. Bregeault. Preparation of various onium tetrakis (oxodiperoxomolybdo) phosphates. III. Structure and reactivity towards olefins under biphasic conditions. New J. Chem. 17: 367-75 (1993).
37. R.M. Carman and K.D. Klika. The four diepoxides of R-(+)-limonene. Aust. J. Chem. 44: 1803-1808 (1991).