Skip to main content
Log in

Nuclear magnetic resonance spectroscopic analysis of homoallylic andbis homoallylic substituted methyl fatty ester derivatives

  • Article
  • Published:
Lipids

Abstract

Using a combination of selective irradiation1H nuclear magnetic resonance experiments and two-dimensional1H−13C correlation spectroscopy spectral analysis of homoallylic andbis homoallylic substituted (azido, acetoxy, chloro and oxo) fatty ester derivatives, the carbon shifts of the ethylenic carbon atoms were determined. In the case of methyl 12-azido-9Z-octadecenoate (homoallylic), the carbon chemical shifts of the ethylenic C-9 and C-10 carbon nuclei are 133.092 and 124.596 ppm, respectively. In methyl 9-azido-12Z-octadecenoate (bis homoallylic), the carbon chemical shift of the ethylenic C-12 and C-13 carbon nuclei are 128.118 and 131.243 ppm, respectively.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Abbreviations

COSY:

correlation spectroscopy

NMR:

nuclear magnetic resonance

TMS:

tetramethylsilane

References

  1. Wenkert, E., Buckwalter, B.L., Burfitt, I.R., Gasic, M.J., Gottlieb, H.E., Hagaman, E.W., Schell, F.M., and Wovkulich, P.M. (1976) inTopics in Carbon-13 NMR Spectroscopy, vol. 2 (Levy, G.C., ed.) John Wiley & Sons, New York.

    Google Scholar 

  2. Bascetta, E., and Gunstone, F.D. (1985)Chem. Phys. Lipids 36, 253–261.

    Article  CAS  Google Scholar 

  3. Dauzonne, D., Demerseman, P., Egyed, J., Lang, C., Platzer, N., and Royer, R. (1977)Tetrahedron 33, 19–25.

    Article  CAS  Google Scholar 

  4. Radeglia, R., Poleschner, H., and Heydenreich, M. (1991)Magnetic Res. Chem. 29, 1028–1035.

    Article  CAS  Google Scholar 

  5. Bernassau, J.M., and Fetizon, M. (1981)Tetrahedron 37, 2105–2109.

    Article  CAS  Google Scholar 

  6. Pfeffer, P.E., Sonnet, P.E., Schwartz, D.P., Osman, S.F., and Weisleder, D. (1992)Lipids 27, 285–288.

    PubMed  CAS  Google Scholar 

  7. Rakoff, H., Weisleder, D., and Emken, E.A. (1979)Lipids 14, 81–83.

    Article  CAS  Google Scholar 

  8. Carlson, K.D., Chaudhry, A., Peterson, R.E., and Bagby, M.O. (1990)J. Am. Oil Chem. Soc. 67, 495–498.

    CAS  Google Scholar 

  9. Husain, S., Kifayatullah, M., Sastry, G.S.R., and Raju, N.P. (1993)J. Am. Oil Soc. 70, 1251–1254.

    CAS  Google Scholar 

  10. Camps, F., Hospital, S., Rosell, G., Delgado, A., and Guerrero, A. (1992)Chem. Phys. Lipids 61, 157–167.

    Article  PubMed  CAS  Google Scholar 

  11. Barabas, A., Botar, A.A., Gocan, A., Popovici, N., and Hodosan, F. (1978)Tetrahedron 34, 2191–2194.

    Article  CAS  Google Scholar 

  12. Disselnkotter, H., Eiter, K., Karl, W., and Wendisch, D. (1976)Tetrahedron 32, 1591–1595.

    Article  Google Scholar 

  13. Gunstone, F.D., inAdvances in Lipid Methodology—Two (1993) p. 13 (W.W. Christie, ed.) The Oily Press, Dundee.

    Google Scholar 

  14. Lie Ken Jie, M.S.F., and Cheng, K.L. (1993)Nat. Prod. Letters 3, 65–69.

    Google Scholar 

  15. Pfeffer, P.E., Sonnet, P.E., Schwartz, D.P., Osman, S.F., and Weisleder, D. (1994)Lipids 29, 913.

    CAS  Google Scholar 

  16. Lie Ken Jie, M.S.F., and Lam, C.H. (1977)Chem. Phys. Lipids 20, 1–12.

    Article  Google Scholar 

  17. Lie Ken Jie, M.S.F., Chan, H.W.M., Wai, J.S.M., and Sinha, S. (1981)J. Am. Oil Chem. Soc. 58, 705–706.

    CAS  Google Scholar 

  18. Lie Ken Jie, M.S.F., and Ahmad, F. (1983)J. Am. Oil Chem. Soc. 60, 1783–1785.

    Google Scholar 

  19. Lie Ken Jie, M.S.F., and Lao, H.B. (1987)Chem. Phys. Lipids 45, 65–74.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

About this article

Cite this article

Lie Ken Jie, M.S.F., Cheng, K.L. Nuclear magnetic resonance spectroscopic analysis of homoallylic andbis homoallylic substituted methyl fatty ester derivatives. Lipids 30, 115–120 (1995). https://doi.org/10.1007/BF02538263

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02538263

Keywords

Navigation