Skip to main content
SpringerLink
Log in

Identification of novel octadecadienoic fatty acids in the seaweedCladophora rupestris through oxidative ozonolysis of the alcohols prepared from the acids

  • Published:
Lipids

Abstract

The BF3−MeOH reagent for ozonolysis of ethylenic unsaturation does not oxidize alcohols. It is therefore feasible to determine the position of ethylenic unsaturation in long chain fatty alcohols of synthetic or natural origin by recovering the methyl ester products intact and silylating the alcohol function of half-ester, half-alcohol, products prior to gas liquid chromatographic analysis. The C3 fragment from methylene-interrupted alkyl chains is not recovered, but, by first reducing carboxyl ester groups to alcohols, the terminal difunctional products can be identified in nonmethylene-interrupted dienoic fatty acids. The seaweedCladophora rupestris is shown to contain Δ5,Δ11-,Δ8,Δ11-, and Δ11, Δ14- as well as Δ9,Δ12-octadecadienoic acid.

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. Sargent, J.R., R.R. Gatten, and R. McIntosh, Mar. Chem. 5:573 (1977).

    Article  CAS  Google Scholar 

  2. Ackman, R.G., B.A. Linke, and J. Hingley, J. Fish. Res. Board Can. 31:1812 (1974).

    CAS  Google Scholar 

  3. Pascal, J.-C. and R.G. Ackman, Chem. Phys. Lipids 16:219 (1976).

    Article  CAS  Google Scholar 

  4. Ratnayake, W.N., M. Sc. Thesis, Dalhousie University, 1977.

  5. Ackman, R.G., Lipids 12:293 (1977).

    Article  CAS  Google Scholar 

  6. Sebedio, J-L., and R.G. Ackman, Can. J. Chem. 56:2480 (1978).

    Article  CAS  Google Scholar 

  7. Ackman, R.G., S.N. Hooper, and D.L. Hooper, J. Am. Oil Chem. Soc. 51:42 (1974).

    CAS  Google Scholar 

  8. Sebedio, J-L., and R.G. Ackman, J. Am. Oil. Chem. Soc. 56:15 (1979).

    CAS  Google Scholar 

  9. Kleiman, R., G.F. Spencer, F.R. Earle, and I.A. Wolff, Lipids 4:135 (1969).

    Article  CAS  Google Scholar 

  10. Johnston, A.E., H.J. Dutton, C.R. Scholfield, and R.O. Butterfield, J. Am. Oil Chem. Soc. 55486 (1978).

    CAS  Google Scholar 

  11. Christie, W.W., J. Chromatogr. 34:405 (1968).

    Article  CAS  Google Scholar 

  12. Gunstone, F.D., I.A. Ismail, and M. Lie Ken Jie, Chem. Phys. Lipids 1:376 (1967).

    Article  CAS  Google Scholar 

  13. Gunstone, F.D., and M. Lie Ken Jie, Chem. Phys. Lipids 4:131 (1970).

    Article  CAS  Google Scholar 

  14. Lie Ken Jie, M.S.F., and C.H. Lam, J. Chromatogr. 124:147 (1976).

    Article  CAS  Google Scholar 

  15. Ackman, R.G., J. Chromatogr. 47:534 (1970).

    Article  Google Scholar 

  16. Ackman, R.G., and J-L. Sebedio, J. Chromatogr. Sci. 16:204 (1978).

    CAS  Google Scholar 

  17. Christie, W.W., J. Chromatogr. 37:27 (1968).

    Article  CAS  Google Scholar 

  18. Ackman, R.G., A. Manzer and J. Joseph, Chromatographia 7:107 (1974).

    Article  CAS  Google Scholar 

  19. Ackman, R.G., and S.N. Hooper, J. Chromatogr. 86:73 (1973).

    Article  CAS  Google Scholar 

  20. Ackman, R.G., P.M. Jangaard, R.J. Hoyle, and H. Brockerhoff, J. Fish. Res. Board Can. 21:74 (1963).

    Google Scholar 

  21. Jamieson, G.R., and E.H. Reid, Phytochemistry 11:1423 (1973).

    Article  Google Scholar 

  22. Ackman, R.G., and j. McLachlan, Proc. N.S. Inst. Sci. 28:47 (1977).

    CAS  Google Scholar 

  23. Hitchcock, C., in “Recent Advances in the Chemistry and Biochemistry of Plant Lipids,” Edited by T. Galliard and E.I. Mercer, Academic Press, London, 1975, p. 1.

    Google Scholar 

  24. Ackman, R.G., C.A. Eaton, and B.A. Linke, Fishery Bull. 73:838 (1975).

    CAS  Google Scholar 

  25. Pearce, R.E., and L.W. Stillway, Lipids 12:544 (1977).

    Article  PubMed  CAS  Google Scholar 

  26. Spencer, G., R.D. Plattner, and T. Miwa, J. Am. Oil Chem. Soc. 54:187 (1977).

    CAS  Google Scholar 

  27. Strocchi, A., and G. Bonaga, Riv. Ital. Sost. Grasse 60:450 (1974).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, Dalhousie University, B3H 4J3, Halifax, N.S., Canada

    W. N. Ratnayake

  2. Fisheries and Oceans Canada, Fisheries and Marine Service, PO Box 550, B3J 2S7, Halifax, N.S., Canada

    R. G. Ackman

Authors
  1. W. N. Ratnayake
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. G. Ackman
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Ratnayake, W.N., Ackman, R.G. Identification of novel octadecadienoic fatty acids in the seaweedCladophora rupestris through oxidative ozonolysis of the alcohols prepared from the acids. Lipids 14, 580–584 (1979). https://doi.org/10.1007/BF02533536

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02533536

Keywords

Search

Navigation