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Mass spectra of acetylenic fatty acid methyl esters and derivatives

  • Published:
Lipids

Abstract

A series of isomeric methyl octadecynoates was analyzed by mass spectrometry; each isomer gave a unique spectrum. The characteristic ions were those resulting from a McLafferty rearrangement of the allenic sites or of the already-rearranged allenic sites. The acetylenic esters were also subjected to oxymercuration whereupon a carbonyl group was formed at either of the original actylenic carbon atoms providing two oxostearates. Further reaction with NaBH4 formed hydroxy esters which, after silylation, gave diagnostic mass spectra indicative of the triple bond location. Applied to esters with both double and triple bonds, this procedure permitted differentiation between the two types of unsaturation. Methoxyl groups marked the original double bond locations and hydroxyls did so for triple bonds.

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References

  1. Bohlmann, F., D. Schumann, H. Bethke, and C. Zdero, Chem. Ber. 100:3706 (1967).

    CAS  Google Scholar 

  2. Groff, T.M., H. Rakoff, and R.T. Holman, Ark. Kemi 29:179 (1968).

    CAS  Google Scholar 

  3. Sun, K.K. and R.T. Holman, JAOCS 45:810 (1968).

    CAS  Google Scholar 

  4. Odham, G., and E. Stenhagen, “Biochemical Applications of Mass Spectrometry,” Edited by George R. Waller, Wiley-Interscience, New York, NY, 1972, p. 223.

    Google Scholar 

  5. Abley, P., F.J. McQuillin, D.E. Minnikin, K. Kusamran, K. Maskena, and N. Polgar, Chem. Commun. 1970:348.

  6. Barve, J.A., and F.D. Gunstone, Chem. Phys. Lipids 7:311 (1971).

    Article  CAS  Google Scholar 

  7. Spencer, G.F., R. Kleiman, F.R. Earle, and I.A. Wolff, Anal. Chem. 41:1874 (1969).

    Article  CAS  Google Scholar 

  8. Kleiman, R., and G.F. Spencer, JAOCS 50:31 (1973).

    CAS  Google Scholar 

  9. Myddleton, W.W., R.G. Berchem, and A.W. Barrett, J. Am. Chem. Soc. 49:2264 (1927).

    Article  CAS  Google Scholar 

  10. Ryhage, R., and E. Stenhagen, Ark. Kemi 15:545 (1960).

    CAS  Google Scholar 

  11. Eglinton, G., D.H. Hunneman, and A. McCormick, Org. Mass Spectrom. 1:593 (1968).

    Article  CAS  Google Scholar 

  12. Richter, W.J., and A.L. Burlingame, Chem. Commun. 1968:1158.

  13. Gunstone, F.D., and R.P. Inglis, Chem. Phys. Lipids 10:73 (1973).

    Article  CAS  Google Scholar 

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Author notes

  1. F. D. Gunstone & J. A. Barve

    Present address: Chemistry Department, the University of St. Andrews, Scotland

Authors and Affiliations

  1. Northern Regional Research Center, ARS, USDA, 61604, Peoria, Illinois

    R. Kleiman, M. B. Bohannon, F. D. Gunstone & J. A. Barve

Authors
  1. R. Kleiman
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  2. M. B. Bohannon
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  3. F. D. Gunstone
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  4. J. A. Barve
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Kleiman, R., Bohannon, M.B., Gunstone, F.D. et al. Mass spectra of acetylenic fatty acid methyl esters and derivatives. Lipids 11, 599–603 (1976). https://doi.org/10.1007/BF02532872

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  • DOI: https://doi.org/10.1007/BF02532872

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