Abstract
Transformations of hydroxy to keto fatty esters have been monitored successfully by converting the hydroxy compounds to their trifluoroacetyl (TFA) or trimethylsilyl (TMS) derivatives followed by gas-liquid chromatography (GLC). The TFA derivatives have shorter retention times, are better separated from the keto esters, and permit more complete resolution of saturated and unsaturated hydroxy fatty esters than the TMS derivatives. Improved methods for derivative preparation which are rapid and convenient are described. Methyl dimorphecolate (methyl 9-hydroxy-trans,trans,10,12-octadecadienoate), which is thermally unstable and cannot be chromatographed as the trifluoroacetate or free hydroxy compound, was chromatographed satisfactorily as the trimethylsilyl ether.
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References
O’Brien, J. S., and G. Rouser, Anal. Biochem.7, 288–296 (1964).
Kishimoto, Y., and N. S. Radin, J. Lipid Res.4, 130–138 (1963).
Tulloch, A. P., JAOCS41, 833–836 (1964).
Morris, L. J., R. T. Holman and K. Fontell, J. Lipid Res.1, 412–420 (1960).
Kishimoto, Y., and N. S. Radin, Ibid. 72–78 (1959).
Wood, R. D., P. K. Raju and R. Reiser, JAOCS42, 81–85 (1965).
Radin, N. S., Ibid. 569–580 (1965).
Morrissette, R. A., and W. E. Link, J. Gas Chrom.3, 67–68 (1965).
Wood, R. D., E. L. Bever and F. Snyder. Presented at AOCS meeting, Los Angeles, April, 1966.
Wood, R. D., P. K. Raju and R. Reiser, JAOCS42, 161–165 (1965).
Swern, D., and E. F. Jordan, Jr., Biochem. Prep.2, 104–105 (1952).
Freedman, B., and T. H. Applewhite, JAOCS43, 125–127 (1966).
Freedman, B., and T. H. Applewhite, Ibid. 342–344 (1966).
Diamond, M. J., R. E. Knowles, R. G. Binder and L. A. Goldblatt, Ibid. 430–433 (1964).
Freedman, B., R. G. Binder and T. H. Applewhite, Ibid. 458–460 (1966).
Sweeley, C. C., R. Bentley, M. Makita and W. W. Wells, J. Am. Chem. Soc.85, 2497–2507 (1963).
Freedman, B., J. S. Nelson, R. G. Binder and T. H. Applewhite, JAOCS42, 340–344 (1965).
Smith, C. R., Jr., T. L. Wilson, E. H. Melvin and I. A. Wolff, J. Am. Chem. Soc.82, 1417–1421 (1960).
Hopkins, C. Y., and M. J. Chisholm, Can. J. Chem.43, 3160–3164 (1965).
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W. Utiliz. Res. Dev. Div., ARS, USDA.
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Freedman, B. Gas-liquid chromatography of hydroxy fatty esters: Comparison of trifluoroacetyl and trimethylsilyl derivatives. J Am Oil Chem Soc 44, 113–116 (1967). https://doi.org/10.1007/BF02558166
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DOI: https://doi.org/10.1007/BF02558166