Skip to main content
SpringerLink
Log in

Separation and spectral data of the six isomeric ozonides from methyl oleate

  • Article
  • Published:
Lipids

Abstract

The structures of the products obtained on ozonation of methyl oleate have been re-examined. The assignments for the six isomeric ozonides of methyl oleate have been made by1H and13C nuclear magnetic resonance (NMR), which were consistent with the retention times observed in high-performance liquid chromatography; the assignments were confirmed by mass and infrared spectroscopy. Two triplets for the ozonide ring protons of thecis andtrans isomers in the normal (MOO1) and the two cross ozonides (MOO1 and MOO3) can be resolved by 400 MHz NMR. For MOO1 and MOO3, where the two ring carbons are equivalent, two peaks for the ring carbons of each cross ozonides are resolved in the13C NMR spectra, one for thecis and one for thetrans isomer. For MOO2, four peaks for the ring carbons are resolved in the13C NMR spectra, two for thecis and two for thetrans isomer.

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

Abbreviations

CI:

chemical ionization

FT-IR:

Fourier transform infrared

HPLC:

high-performance liquid chromatography

IR:

infrared

MOO1:

one of the cross ozonides from methyl oleate (3,5-dioctyl-1,2,4-trioxolane)

MOO2:

the normal ozonide from methyl oberte (methyl 5-octyl-1,2,4-trioxolane-3-(8′ octanoate))

MOO3:

the second cross ezonide from methyl oleate (dimethyl 1,2,4-trioxolane-3,5-(8′,8′-dioctanoate))

MOO1:

MOO2, and MOO3 refer to bothcis andtrans isomers (see Scheme 1 for structures of the six isomeric ozenides)

NMR:

nuclear magnetic resonance

TLC:

thin-layer chromatography

References

  1. Bailey, P.S. (1978)Ozonation in Organic Chemistry, Vol. I, Academic Press, New York.

    Google Scholar 

  2. Riezebos, G., Grimmelikhuysen, J.C., and Van Dorp, D.A. (1963)Rec. Trav. Chim. 82, 1234–1244.

    Article  CAS  Google Scholar 

  3. Privett, O.S., and Nickell, E.C. (1963)J. Lipid Res. 4, 208–211.

    PubMed  CAS  Google Scholar 

  4. Privett, O.S., and Nickell, E.C. (1964)J. Am. Oil Chem. Soc. 41, 72–77.

    CAS  Google Scholar 

  5. Lorenz, O., and Parks, C.R. (1965)J. Org. Chem. 30, 1976–1981.

    Article  CAS  Google Scholar 

  6. Loan, L.D., Murray, R.W., and Story, P.R. (1965)J. Am. Chem. Soc. 87, 737–741.

    Article  CAS  Google Scholar 

  7. Greenwood, F.L. (1966)J. Am. Chem. Soc. 88, 3146–3147.

    Article  CAS  Google Scholar 

  8. Murray, R.W. (1968)Acc. Chem. Res. 1, 313–320.

    Article  CAS  Google Scholar 

  9. Fliszar, S., and Carles, J. (1969)Can. J. Chem. 47, 3921–3929.

    Article  CAS  Google Scholar 

  10. Bailey, P.S., Ferrell, T.M., Rustaiyan, A., Seyhan, S., and Unruh, L.E. (1978)J. Am. Chem. Soc. 100, 894–898.

    Article  CAS  Google Scholar 

  11. Keul, H., and Kuczkowski, R.L. (1985)J. Org. Chem. 50, 3371–3376.

    Article  CAS  Google Scholar 

  12. Cortesi, R., and Privett, O.S. (1972)Lipids, 7, 715–720.

    Article  PubMed  CAS  Google Scholar 

  13. Takatori, T., and Privett, O.S. (1974)Lipids 9, 1018–1023.

    Article  PubMed  CAS  Google Scholar 

  14. Menzel, D.B., Slaughter, R.J., Bryant, A.M., and Jauregui, H.O. (1975)Arch. Environ. Health 30, 296–301.

    PubMed  CAS  Google Scholar 

  15. Menzel, D.B., Slaughter, R.J., Bryant, A.M., and Jauregui, H.O. (1975)Arch. Environ. Health 30, 234–236.

    PubMed  CAS  Google Scholar 

  16. Calabrese, E.J., Williams, P.S., and Moore, G.S. (1983)Ecotoxicol. Environ. Saf. 7, 416–422.

    Article  PubMed  CAS  Google Scholar 

  17. Calabrese, E.J., Moore, G.S., and Williams, P. (1982)Bull. Environ. Contam. Toxicol. 29, 498–504.

    Article  PubMed  CAS  Google Scholar 

  18. Vos, R.M.E., Rietjens, I.M.C.M., Stevens, L.H., and Van Bladeren, P.J. (1989)Chem. Biol. Interact. 69, 269–278.

    Article  PubMed  CAS  Google Scholar 

  19. Rietjens, I.M.C.M., Lemmink, H.H., Alink, G.M., and Van Bladeren, P.J. (1987)Chem. Biol. Interact. 62, 3–14.

    Article  PubMed  CAS  Google Scholar 

  20. Ewing, J.C., Cosgrove, J.P., Giamalva, D.H., Church, D.F., and Pryor, W.A. (1989)Lipids 24, 609–615.

    PubMed  CAS  Google Scholar 

  21. Wu, M. (1991) Ph.D. Dissertation, Louisiana State University.

  22. Pryor, W.A. (1991)Am. J. Clin. Nutr. 53, 702–722.

    PubMed  CAS  Google Scholar 

  23. Pryor, W.A., and Church, D.F. (1991)Free Radical Biol. Med. 11, 41–46.

    Article  CAS  Google Scholar 

  24. Pryor, W.A., Miki, M., Das, B., and Church, D.F. (1991)Chem. Biol. Interact. 79, 41–52.

    Article  PubMed  CAS  Google Scholar 

  25. Pryor, W.A., Church, D.F., and Das, B. (1991)Chem. Res. Toxicol. 4, 341–348.

    Article  PubMed  CAS  Google Scholar 

  26. Menzel, D.B. (1984)J. Toxicol. Environ. Health 13, 183–204.

    Article  PubMed  CAS  Google Scholar 

  27. Mudd, J.B., and Freeman, B.A. (1977) inBiochemical Effects of Environmental Pollutants (Lee, S.D., ed.), pp. 97–133, Ann Arbor Science Publishers, Ann Arbor, MI.

    Google Scholar 

  28. Evans, L.S., and Ting, I.P. (1973)Am. J. Bot. 60, 155–162.

    Article  CAS  Google Scholar 

  29. Perchorowicz, J.T., and Ting, I.P. (1974)Am. J. Bot. 61, 787–793.

    Article  CAS  Google Scholar 

  30. Sanders, R.L. (1982) inLung Development: Biological and Clinical Perspectives (Farrell, P.M., ed.) Vol. I, p. 198, Academic Press, New York.

    Google Scholar 

  31. Tanford, C. (1980)The Hydrophobic Effect: Formation of Micelles and Biological Membranes, 2nd edn., Chapter 11, John Wiley & Sons, New York.

    Google Scholar 

  32. Criegee, R., Bath, S.S., and Von Bornhaupt, B. (1960)Chem. Ber. 93, 2891–2897.

    CAS  Google Scholar 

  33. Criegee, R., and Korber, H. (1971)Chem. Ber. 104, 1807–1811.

    CAS  Google Scholar 

  34. Kolsaker P. (1965)Acta Chem. Scand. 19, 223–228.

    Article  CAS  Google Scholar 

  35. Roehm, J.N., Hadley, J.G., and Menzel, D.B. (1971)Arch. Environ. Health 23, 142–148.

    PubMed  CAS  Google Scholar 

  36. Loan, L.D., Murray, R.W., and Story, P.R. (1965)J. Am. Chem. Soc. 87, 737–741.

    Article  CAS  Google Scholar 

  37. Bishop, C.E., Denson, D.D., and Story, P.R. (1968)Tetrahedron Lett., 5739–5742.

  38. Miura, M., Nagase, S., Nojima, M., and Kusabayashi S. (1983)J. Org. Chem. 48, 2366–2370.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. The Chemistry Department, Louisiana State University, 70803-1800, Baton Rouge, Louisiana

    Mingdan Wu, Daniel F. Church & William A. Pryor

  2. Biodynamics Institute, Louisiana State University, 711 Choppin, 70803-1800, Baton Rouge, LA

    Mingdan Wu, Daniel F. Church & William A. Pryor

  3. The Department of Physiology, Pharmacology, and Toxicology, School of Veterinary Medicine Louisiana State University, 70803-8420, Baton Rouge, Louisiana

    Thomas J. Mahier & Steven A. Barker

Authors
  1. Mingdan Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Daniel F. Church
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Thomas J. Mahier
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Steven A. Barker
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. William A. Pryor
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Wu, M., Church, D.F., Mahier, T.J. et al. Separation and spectral data of the six isomeric ozonides from methyl oleate. Lipids 27, 129–135 (1992). https://doi.org/10.1007/BF02535812

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02535812

Keywords

Search

Navigation