Large-scale preparation of linoleic acid-d2-enriched triglycerides fromCrepis alpina seed oil

  • Richard O. Adlof
  • Edward A. Emken
Short Communication

Abstract

Catalytic deuteration ofCrepis alpina seed oil provided a convenient one-step method for the direct synthesis of large quantities of triglycerides enriched with deuteriumlabelled linoleic acid.Crepis alpina seed (19 kg) was crushed, and the oil [74% crepenynic acid (cis-9-octadecen-12-ynoic acid)] was extracted with hexane. After purification by column chromatography (silica gel), > 170-g batches of oil were deuterated with Lindlar catalyst and deuterium (D2) gas. Purification (silica gel) resulted in > 150-g samples of triglyceride containing 74%cis-9,cis-12-octadecadienoic acid-12,13-d2 (18:2-d2) and 14% unlabelled linoleic acid. Pure (> 99%) tricrepenynin was recovered by further fractionation of theCrepis alpina triglycerides on silica gel. Deuteration of this sample produced deuteriumlabelled trilinolein containing linoleic acid-d2 of > 98% isotopic purity.

Key words

Acetylenic fatty acids and esters C18 fatty acids and derivatives crepis oil seeds and crepenynic acid deuterium and deuteration linoleic acid and esters 

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References

  1. 1.
    Emken, E.A., W.K. Rohwedder, R.O. Adlof, W.J. DeJarlais and R.M. Gulley,Lipids 21:589 (1986).CrossRefGoogle Scholar
  2. 2.
    Hachey, D.L., M.R. Thomas, E.A. Emken, C. Garza, L. Brown-Booth, R.O. Adlof and P.D. Klein,J. Lipid Res. 28:1185 (1987).Google Scholar
  3. 3.
    Emken, E.A., R.O. Adlof, D.L. Hachey, C. Garza, M.R. Thomas and L. Brown-Booth,J. Lipid Res. 30:395 (1989).Google Scholar
  4. 4.
    Emken, E.A., R.O. Adlof, H. Rakoff and W.K. Rohwedder, inSynthesis and Appliction of Isotopically Labelled Compounds, proceedings from symposium held July 17–21, 1988, Innsbruck, Austria, edited by T.A. Baille and J.R. Jones, Elsevier Science Publishers, 1989, p. 713.Google Scholar
  5. 5.
    Emken, E.A., R.O. Adlof, H. Rakoff, W.K. Rohwedder and R.M. Gulley,Biochem. Soc. Trans. 18:766 (1990).Google Scholar
  6. 6.
    Emken, E.A., R.O. Adlof, H. Rakoff, W.K. Rohwedder and R.M. Gulley,Nutrition 8:213 (1992).Google Scholar
  7. 7.
    Rohwedder, W.K., E.A. Emken and D.J. Wolf,Lipids 20:303 (1985).CrossRefGoogle Scholar
  8. 8.
    Tucker, W.P., S.B. Tove and C.R. Kepler,J. Label. Comp. Radiopharm. 7:11 (1971).CrossRefGoogle Scholar
  9. 9.
    Adlof, R.O., and E.A. Emken,Chem. Phys. Lipids 29:3 (1981).CrossRefGoogle Scholar
  10. 10.
    Rakoff, H., and E.A. Emken,J. Am. Oil Chem. Soc. 60:546 (1983).Google Scholar
  11. 11.
    Adlof, R.O., H. Rakoff and E.A. Emken, Ibid.:303 (1991).Google Scholar
  12. 12.
    Rohwedder, W.K.,Rev. Sci. Instr. 37:1734 (1966).CrossRefGoogle Scholar
  13. 13.
    Lanser, A.C., and E.A. Emken,J. Am. Oil Chem. Soc. 65:1483 (1988).Google Scholar
  14. 14.
    Gunstone, F.D.,The Lipid Handbook, edited by F.D. Gunstone, J.L. Harwood and F.B. Padley, Chapman and Hall, London, 1986, p. 4.Google Scholar
  15. 15.
    Neff, W.E., R.O. Adlof, H. Konishi and D. Weisleder,J. Am. Oil Chem. Soc. 70:449 (1993).Google Scholar

Copyright information

© American Oil Chemists’ Society 1993

Authors and Affiliations

  • Richard O. Adlof
    • 2
  • Edward A. Emken
    • 2
  1. 1.USDA, ARS, NCAURPeoria
  2. 2.USDA, ARS, Food Quality and Safety Research UnitPeoria

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