Abstract
In this paper, an alternative base-catalyzed methodology for the facile derivatization in mild conditions of lipid TAG prior to FA analysis is proposed. Reagents were prepared by proton exchange between potassium tert-butoxide and either ethanol, n-propanol, n-butanol, or 2-methoxyethanol and used for the synthesis, at 40°C for 15 min, of the corresponding derivatives, which were directly analyzed by GC. This methodology can be used on a routine basis and has been applied to standard and complex natural lipid samples. Tripalmitin was used to determine optimal reaction conditions; and bovine milk fat, containing C4 to C22 acids, and celery (Apium graveolens) seed oil, characterized by a high level of petroselinic acid, were comparatively analyzed as their ethyl, n-propyl, n-butyl, and 2-methoxyethyl esters.
Similar content being viewed by others
References
Christie, W.W. (1990) Preparation of Methyl Esters—Part 1, Lipid Technol. 2, 48–49.
Christie, W.W. (1990) Preparation of Methyl Esters—Part 2, Lipid Technol. 2, 79–80.
Metcalfe, L.D., and Schmitz, A.A. (1961) The Rapid Preparation of Fatty Acid Esters for Gas Chromatography Analysis, Anal. Chem. 33, 363–364.
Morrison, W.R., and Smith, L.M. (1964) Preparation of Fatty Acid Methyl Esters and Dimethyl Acetals from Lipids with Boron Fluoride-Methanol, J. Lipid Res. 5, 600–608.
Wolff, R.L., and Castera-Rossignol, A.M.F. (1987) Mise au Point et Évaluation d’une Méthode d’Extraction de la Matière Grasse de Fromage de Type Emmenthal, Rev. Fr. Corps Gras 34, 123–132.
Wolff, R.L., and Fabien, R.J. (1989) Utilisation de l’Isopropanol pour l’Extraction de la Matière Grasse de Produits Laitiers et Pour l’Estérification Subséquente des Acides Gras, Lait 69, 33–46.
Wolff, R.L., Bayard, C.C., and Fabien, R.J. (1995) Evaluation of Sequential Methods for the Determination of Butterfat Fatty Acid Composition with Emphasis on trans-18∶1 Acids. Application to the Study of Seasonal Variations in French Butters, J. Am. Oil Chem. Soc. 72, 1471–1483.
Wolff, R.L. (1995) Content and Distribution of trans-18∶1 Acids in Ruminant Milk and Meat Fats. Their Importance in European Diets and Their Effect on Human Milk, J. Am. Oil Chem. Soc. 72, 259–272.
Wolff, R.L., and Vandamme, F.F. (1992) Separation of Petroselinic (cis-6 18∶1) and Oleic (cis-9 18∶1) Acids by Gas-Liquid Chromatography of Their Isopropyl Esters, J. Am. Oil Chem. Soc. 69, 1228–1231.
Wolff, R.L. (1998) Comments on the Methodology for the Separation and Quantification of cis-6 (Petroselinic) and cis-9 (Oleic) Acids, J. Am. Oil Chem. Soc. 75, 893–894.
Wolff, R.L. (1995) Recent Applications of Capillary Gas-Liquid Chromatography to Some Difficult Separations of Positional or Geometrical Isomers of Unsaturated Fatty Acids, in New Trends in Lipid and Lipoprotein Analysis (Sébédio, J.L., and Perkins, R.G., eds.), pp. 147–180, AOCS Press, Champaign.
Wolff, R.L. (1992) Resolution of Linolenic Acid Geometrical Isomers by Gas-Liquid Chromatography of a Capillary Column Coated with a 100% Cyanopropyl Polysiloxane Film (CP Sil 88), J. Chromatogr. Sci. 30, 17–22.
Wolff, R.L. (1992) Applications Récentes de la Colonne Capillaire CP Sil 88 à la Séparation par CPG d’Isomères Positionnels on Géométriques d’Acides Gras Polyrnsaturés d’Origine Biologique ou Alimentaire, Spectra 2000, 165, 41–46.
Wolff, R.L. (1993) Further Studies on Artificial Geometrical Isomers of α-Linolenic Acid in Edible Linolenic Acid-Containing Oils, J. Am. Oil Chem. Soc. 70, 219–224.
Wolff, R.L. (1993) Heat-Induced Geometrical Isomerization of α-Linolenic Acid: Effect of Temperature and Heating Time on the Appearance of Individual Isomers, J. Am. Oil Chem. Soc. 70, 425–430.
Lavillonière, F., Martin, J.C., Bougnoux, P., and Sébédio, J.L. (1998) Analysis of Conjugated Linoleic Acid Isomers and Content in French Cheeses, J. Am. Oil Chem. Soc. 75, 343–352.
Iverson, J.L., and Sheppard, A.J. (1977) Butyl Ester Preparation for Gas-Liquid Chromatographic Determination of Fatty Acid in Butter, J. Assoc. Off. Anal. Chem. 60, 248–258.
Ackman, R.G., and Macpherson, E.J. (1994) Coincidence of cis- and trans-Monoethylenic Fatty Acids Simplifies the Open-Tubular Gas-Liquid Chromatography of Butyl Esters of Butter Fatty Acids, Food Chem. 50, 45–52.
Thies, W. (1995) Determination of the Petroselinic Acid in Seeds of Coriandrum sativum by Gas-Liquid Chromatography as n-Butyl Esters, Fat Sci. Technol. 97, 411–413.
Liu, L., and Hammond, E.G. (1995) Phenylethyl Esters of Fatty Acids for the Analytical Resolution of Petroselinate and Oleate, J. Am. Oil Chem. Soc. 72, 749–751.
Christie, W.W. (1994) Why I Dislike Boron Trifluoride-Methanol, Lipid Technol. 6, 66–68.
Christopherson, S.W., and Glass, R.L. (1969) Preparation of Milkfat Methyl Esters by Alcoholysis in an Essentially Nonalcoholic Solution, J. Dairy Sci. 52, 1289–1290.
Ulberth, F., Gabernig, R.G., and Schrammel, F. (1995) Flame-Ionization Detector Response to Methyl, Ethyl, Propyl, and Butyl Esters of Fatty Acids, J. Am. Oil Chem. Soc. 76, 263–266.
Kramer, J.K.G., Fellner, V., Dugan, M.E.R., Sauer, F.D., Mossoba, M.M., and Yurawecz, M.P. (1997) Evaluating Acid and Base Catalysts in the Methylation of Milk and Rumen Fatty Acids with Special Emphasis on Conjugated Dienes and Total trans Fatty Acids, Lipids 32, 1219–1228.
Precht, D., and Molkentin, J. (1996) Rapid Analysis of the Isomers of trans-Octadecenoic Acid in Milk Fat, Int. Dairy J. 6, 791–809.
Destaillats, F., Arul, J., Simon, J.E., Wolff, R.L., and Angers, P. (2002) Dibutyrate Derivatization of Monoacylglycerols for the Resolution of Regioisomers of Oleic, Petroselinic, and cis-Vaccenic Acids, Lipids 37, 111–116.
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Destaillats, F., Angers, P. Base-catalyzed derivatization methodology for FA analysis. Application to milk fat and celery seed lipid TAG. Lipids 37, 527–532 (2002). https://doi.org/10.1007/s11745-002-0928-9
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11745-002-0928-9