Skip to main content
SpringerLink
Log in

Elucidation of cyclic fatty acid monomer structures. Cyclic and bicyclic ring sizes and double bond position and configuration

  • Published:
Journal of the American Oil Chemists’ Society

Abstract

Gas chromatography (GC)-electron ionization mass spectrometry of 2-alkenyl-4,4-dimethyl-oxazoline derivatives was used to confirm the identities of a complex mixture of C18 diunsaturated cyclic fatty acid monomers (CFAMs) that were isolated from heated flaxseed (linseed) oil. The positions of double bonds and 1,2-disubstituted unsaturated 5- and 6-membered rings along the fatty acid hydrocarbon chains were established by this method. The oxazoline spectra exhibited a homologous ion series with a pattern of peaks that were 14 u (u=atomic mass unit) apart but interrupted when a double bond (12-u mass interval) or a ring was present along the fatty acid chain. The identity and location of a ring were indicated by a large interval of 68, 82, 66, 80, 78, or 120 u for a saturated 5- or 6-membered ring, monounsaturated 5- or 6-membered ring, diunsaturated 6-membered ring, or monounsaturated bicyclic ring system (fused 5- and 6-membered rings), respectively. The double bond configuration for the methyl ester derivatives of these CFAMs was established by GC-matrix isolation-Fourier transform infrared spectroscopy. The elucidated alkenyl structures at C2 in diunsaturated 2-[alkenyl]-4,4-dimethyloxazolines were 8-(2-but-trans-1-enyl-cyclopentenyl)octyl, 9-(2-propyl-cyclopentenyl)non-rans-8-enyl, 9-(2-propyl-cyclopentenyl)non-cis-7-enyl, 8-(2-but-cis-1-enyl-cyclopentenyl)ocytl, 9-(2-propylcyclopentenyl)non-cis-8-enyl, 8-(2-propyl-cyclohex-cis-4-enyl)oct-trans-7-enyl, 8-(prop-trans-1-enyl-cyclohex-cis-4-enyl)ocytl, and 8-(2-propylcyclohexa-cis,cis-3,5-dienyl)octyl.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Sebedio, J.L., and A. Grandgirard,Prog. Lipid Res. 28:303 (1989).

    Article  CAS  Google Scholar 

  2. Hutchison, R.B., and J.C. Alexander,J. Org. Chem. 28:2522 (1963).

    Article  CAS  Google Scholar 

  3. Friedrich, J.P.,J. Am. Oil Chem. Soc. 44:244 (1967).

    Article  CAS  Google Scholar 

  4. Graille, J., A. Bonfand, P. Perfetti and M. Naudet,Chem. Phys. Lipids 27:23 (1980).

    Article  CAS  Google Scholar 

  5. Awl, R.A., and E.N. Frankel,Lipids 17:414 (1982).

    Article  CAS  Google Scholar 

  6. Vatele, J.M., J.-L. Sebedio and J.L. Le Quere,Chem. Phys. Lipids 48:119 (1988).

    Article  Google Scholar 

  7. Rojo, J.A., and E.G. Perkins,J. Am. Oil Chem. Soc. 66:1593 (1989).

    CAS  Google Scholar 

  8. Le Quere, J.L., J.-L. Sebedio, R. Henry, F. Couderc, N. Demont and J.C. Prome,J. Chromatogr. 562:659 (1991).

    Article  Google Scholar 

  9. MacDonald, J.A.,J. Am. Oil Chem. Soc. 33:394 (1956).

    Article  CAS  Google Scholar 

  10. McInnes, A.G., F.P. Cooper and J.A. MacDonald,Can. J. Chem. 39:1906 (1961).

    Article  CAS  Google Scholar 

  11. Gast, L.E., W.J. Schneider, C.A. Forest and J.C. Cowan,J. Am. Oil Chem. Soc. 40:287 (1963).

    CAS  Google Scholar 

  12. Saito, M., and T. Kaneda,Yukagaku 25:79 (1976).

    CAS  Google Scholar 

  13. Potteau, B., P. Dubois and J. Rigaud,Ann. Technol. Agric. 27:655 (1978).

    CAS  Google Scholar 

  14. Sebedio, J.L., J. Prevost and A. Grandgirard,J. Am. Oil Chem. Soc. 64:1026 (1987).

    Article  CAS  Google Scholar 

  15. Rojo, J.A., and E.G. Perkins, Ibid.:414 (1987).

    Article  CAS  Google Scholar 

  16. Christie, W.W., E.Y. Brechany, J.-L. Sebedio and J.L. Le Quere,Chem. Phys. Lipids 66:143 (1993).

    Article  CAS  Google Scholar 

  17. Christie, W.W., E.Y. Brechany and V.K.S. Shukla,Lipids 24:116 (1989).

    Article  CAS  Google Scholar 

  18. Sebedio, J.-L., J. Prevost, E. Ribot and A. Grandgirard,J. Chromatogr. A659:101 (1994).

    Article  Google Scholar 

  19. Sebedio, J.-L., J.L. Le Quere, O. Morin, J.M. Vatele and A. Grandgirard,J. Am. Oil Chem. Soc. 66:704 (1989).

    CAS  Google Scholar 

  20. Zhang, J.Y., Q.T. Yu, B.N. Liu and Z.H. Huang,Biomed. Environ. Mass Spectrom. 15:33 (1988).

    Article  CAS  Google Scholar 

  21. Yu, Q.T., B.N. Liu, J.Y. Zhang and Z.H. Huang,Lipids 24:804 (1989).

    Google Scholar 

  22. Zhang, J.Y., N.Y. Wang, Q.T. Yu, X.J. Yu, B.N. Liu and Z.H. Huang,J. Am. Oil Chem. Soc. 66:242 (1989).

    Article  CAS  Google Scholar 

  23. Mossoba, M.M., M.P. Yurawecz, H.S. Lin, J.A.G. Roach, R.E. McDonald, B.D. Flickinger and E.G. Perkins,INFORM 4:514 (1993).

    Google Scholar 

  24. Mossoba, M.M., M.P. Yurawecz, J.A.G. Roach, H.S. Lin, R.E. McDonald, B.D. Flickinger and E.G. Perkins,Lipids 29:893 (1994).

    Article  CAS  Google Scholar 

  25. Bourne, S., G. Reedy, P. Coffey and D. Mattson,Am. Lab. (Fairfield, Conn.) 160:90 (1984).

    Google Scholar 

  26. Reedy, G.T., D.C. Ettinger, J.F. Schneider and S. Bourne,Anal. Chem. 57:1602 (1985).

    Article  CAS  Google Scholar 

  27. Mossoba, M.M., R.A. Niemann and J.-Y.T. Chen, Ibid.:1678 (1989).

    Article  CAS  Google Scholar 

  28. Fay, L., and U. Richly,J. Chromatogr. 541:89 (1991).

    Article  CAS  Google Scholar 

  29. Sebedio, J.-L., J.L. Le Quere, E. Semon, O. Morin, J. Prevost and A. Grandgirard,J. Am. Oil Chem. Soc. 64:1324 (1987).

    Article  CAS  Google Scholar 

  30. Rojo, J.A., and E.G. Perkins,Lipids 24:467 (1989).

    Article  CAS  Google Scholar 

  31. Mossoba, M.M., R.E. McDonald, J.-Y.T. Chen, D.J. Armstrong and S.W. Page,J. Agric. Food Chem. 38:86 (1990).

    Article  CAS  Google Scholar 

  32. Pouchert, C.J. (ed.),Aldrich Library of Infrared Spectra, 3rd edn., Aldrich Chemical Company, Milwaukee, 1981.

    Google Scholar 

  33. Andersson, B.A., and R.T. Holman,Lipids 9:185 (1974).

    Article  CAS  Google Scholar 

  34. Mikusch, J.D., and A.N. Sagredos,Fette Seifen Anstrichm. 73:384 (1971).

    Article  Google Scholar 

  35. Hase, A., S. Kaltia, J. Matikainen, M. Ala-Peijari and T. Hase,J. Am. Oil Chem. Soc. 69:1027 (1992).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. FDA, National Center for Food Safety and Technology, 60501, Summit-Argo, Illinois

    Richard E. McDonald

  2. University of Illinois, 61801, Urbana, Illinois

    Brent D. Flickinger & Edward G. Perkins

  3. Food and Drug Administration (HFS-717), Center for Food Safety and Applied Nutrition, 20204, Washington, DC

    Magdi M. Mossoba, Martin P. Yurawecz, John A. G. Roach & Hubert S. Lin

Authors
  1. Magdi M. Mossoba
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Martin P. Yurawecz
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. John A. G. Roach
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hubert S. Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Richard E. McDonald
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Brent D. Flickinger
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Edward G. Perkins
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Physical science aide, 1991–1992; currently a medical student at the University of Maryland, Baltimore, MD.

About this article

Cite this article

Mossoba, M.M., Yurawecz, M.P., Roach, J.A.G. et al. Elucidation of cyclic fatty acid monomer structures. Cyclic and bicyclic ring sizes and double bond position and configuration. J Am Oil Chem Soc 72, 721–727 (1995). https://doi.org/10.1007/BF02635662

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02635662

Key words

Search

Navigation