Abstract
Mass spectra of several triglycerides of specific structure or with specific deuterium labeling have been measured with a low resolution mass spectrometer. With saturated triglycerides the abundances of ions characteristic of the component acids, [M-RCO2]+, increase with increasing chain length, and [M-RCO2CH2]+ decrease with increasing chain length. Unsaturation in the acyl moiety causes the abundant formation of [RCO-1]+. Structures have been suggested for a number of the main peaks obtained from saturated triglycerides, and high resolution spectra of one triglyceride agree with the postulated structures. The peaks, [RCO+74]+, [RCO+115]+ and [RCO+128+14n]+, represent structures which contain the glyceryl portion of the triglyceride, since in case of the replacement of its hydrogens with deuteriums, these peaks are shifted accordingly. Evidence which indicates the possibility of determining the location of unsaturation by the interruption of homology of the [RCO+128+14n]+ series, brought about by the addition of deuterium to the unsaturated linkages, is introduced. Further evidence is also presented, which indicates that the [M-RCO2CH2]+ ions arise from the positions 1 and 3 and, in agreement with earlier studies from other laboratories, it is thus possible to identify the acyl groups attached to the 1 and 2 positions of the glyceryl moiety.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Ryhage, R., and E. Stenhagen, J. Lipid Res. 1:382 (1960).
Barber, M., T.O. Merren and W. Kelly, Tetrahedron Letters 1063 (1963).
Dinh-Nguyen, Ng, R. Ryhage, S. Stallberg-Stenhagen and E. Stenhagen, Ark. Kemi 18:393 (1961).
Dinh-Nguyen, Ng, Ibid. 28:289 (1968).
Aasen, A., W.M. Lauer and R.T. Holman, Lipids 5:869–877 (1970).
Rohwedder, W.K., C.R. Scholfield, H. Rakoff, J. Nowakowska and H.J. Dutton, Anal. Chem. 39:820 (1967).
King, A.M., and W.E. Garner, J. Chem. Soc. 1936:1372.
Meyer, J.D., and E.E. Reid, J. Amer. Chem. Soc. 55:1574 (1933).
Clarkson, C.E., and T. Malkin, J. Chem. Soc. 1948:985.
Johnson, C.B., and R.T. Holman, Lipids 1:371 (1966).
Baumann, W.J., J. Seufert, H.W. Hayes and R.T. Holman, J. Lipid Res. 10:703 (1969).
Sprecher, H.W., R. Maier, M. Barber and R.T. Holman, Biochemistry 4:1856 (1965).
Malkin, T., and T.H. Bevan in “Progress of the Chemistry of Fats and Other Lipids,” Vol. 4, Edited by R.T. Holman, Pergamon Press, Oxford and New York, 1957, p. 63–77.
Hallgren, B., R. Ryhage and E. Stenhagen, Acta Chem. Scand. 13:845 (1959).
Christie, W.W., and R.T. Holman, Chem. Phys. Lipids 1:407 (1967).
Mutzenbecher, G.V., Z. Pelah, D.H. Williams, H. Budzikiewicz and C. Djerassi, Steroids 2:475 (1963).
Pelah, Z., D.H. Williams, H. Budzikiewicz and C. Djerassi, J. Amer. Chem. Soc. 86:3722 (1964).
Audier, H., A. Diara, M.J. deDurazo, M. Fetizon, P. Foy and W. Vetter, Bull. Soc. Chim. Fr. 1963:2827.
Morrison, A., M.D. Barratt and R. Aneja, Chem. Phys. Lipids 4:47 (1970).
Kramer, J.K.G., and H.K. Mangold, Chem. Phys. Lipids 4:332 (1970).
Author information
Authors and Affiliations
About this article
Cite this article
Lauer, W.M., Aasen, A.J., Graff, G. et al. Mass spectrometry of triglycerides: I. Structural effects. Lipids 5, 861–868 (1970). https://doi.org/10.1007/BF02531117
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02531117