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Localization of fatty acid double bonds by gas chromatography of intermediate aldehydes as 1,3-dioxane

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Lipids

Abstract

A semi-micro quantitative method has been developed for the determination of double bond positions in unsaturated fatty acid methyl esters differing in position, number of double bonds and chain length. This method involves ozonolysis in methylene chloride in the presence of 1,3-propanediol, reduction of the hydroperoxides with dimethyl sulfide and conversion of aldehyde and aldester fragments to stable dioxanes, followed by gas chromatographic analysis under programmed temperature. Propanediol acts as a proton donor for the generation of hydroperoxides as well as a reactant for the formation of dioxanes. All the steps are carried out in a culture tube without any transfers. The absence of unoxidized ester and unreduced hydroperoxide or ozonide has been shown by thin layer chromatography. The method has been tested with pure esters and their binary mixtures. Experimental values for mole percentage composition in the mixtures agreed with the actual values. This method enabled us to isolate and estimate malondialdehyde for the first time as a stable bis-dioxane derivative.

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References

  1. Privett, O.S. (1966)Prog. Chem. Fats Lipids 9, 91–117.

    Article  CAS  Google Scholar 

  2. Minnikin, D.E. (1978)Chem. Phys. Lipids 21, 313–347.

    Article  CAS  Google Scholar 

  3. Ucciani, E., and Pelloquin, A. (1973)Rev. Fr. Corps Gras 20, 397–404.

    CAS  Google Scholar 

  4. Stein, R.A. (1965)J. Am. Oil Chem. Soc. 42, 326–329.

    CAS  Google Scholar 

  5. Wolfrom, M.L., and Bobbit, J.M. (1956)J. Am. Chem. Soc. 78, 2489–2493.

    Article  CAS  Google Scholar 

  6. Stein, R.A., and Nicolaides, N. (1962)J. Lipid Res. 3, 476–478.

    CAS  Google Scholar 

  7. Privett, O.S., and Nickell, E.C. (1966)Lipids 1, 98–103.

    Article  CAS  Google Scholar 

  8. Pappas, J.J., Keaveney, W.P., Gancher, E., and Berger, M. (1966)Tetrahedron Lett. 36, 4273–4278.

    Article  Google Scholar 

  9. Ramachandran, S., Rao, P.V., and Cornwell D.G. (1968)J. Lipid Res. 9, 137–139.

    PubMed  CAS  Google Scholar 

  10. Johnston, A.E., Dutton, H.J., Scholfield, C.R., and Butterfield, R.O. (1978)J. Am. Oil Chem. Soc. 55, 486–490.

    CAS  Google Scholar 

  11. Gray, G.M. (1960)J. Chromatog. 4, 52–59.

    Article  CAS  Google Scholar 

  12. Rao, P.V., Ramachandran, S., and Cornwell, D.G. (1967)J. Lipid Res. 8, 380–390.

    PubMed  CAS  Google Scholar 

  13. Klenk, E., and Debuch, H. (1963)Prog. Chem. Fats Lipids 6, 1–29.

    Article  CAS  Google Scholar 

  14. Perkins, G. Jr., Rouayheb, G.M., Lively, L.D., and Hamilton, W.C. (1962) inGas Chromatography (Brenner, N., Callen, J.E., and Weiss, M.D., eds.) pp. 269–285, Academic Press, New York.

    Google Scholar 

  15. Lakshminarayana, G., Rao, K.V.S.A., Devi, K.S., and Kaimal, T.N.B. (1981)J. Am. Oil Chem. Soc. 58, 838–839.

    CAS  Google Scholar 

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Author notes

  1. Gollamudi Lakshminarayana

    Present address: Department of Physiological Chemistry Regional Research Laboratory, (CSIR), 500007, Hyderabad, India

Authors and Affiliations

  1. 260 Meiling Hall, College of Medicine, Ohio State University, 370 W. 9th Ave., 43210, Columbus, OH

    Gollamudi Lakshminarayana & David G. Cornwell

Authors
  1. Gollamudi Lakshminarayana
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  2. David G. Cornwell
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Lakshminarayana, G., Cornwell, D.G. Localization of fatty acid double bonds by gas chromatography of intermediate aldehydes as 1,3-dioxane. Lipids 21, 175–177 (1986). https://doi.org/10.1007/BF02534442

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  • DOI: https://doi.org/10.1007/BF02534442

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