Journal of the American Oil Chemists’ Society

, Volume 73, Issue 12, pp 1729–1731 | Cite as

Separation and identification of ximenynic acid isomers in the seed oil ofSantalum spicatum R.Br. as their 4,4-dimethyloxazoline derivatives

  • Yandi D. Liu
  • Robert B. Longmore
  • John E. D. Fox
Short Communication


The seed oil ofSantalum spicatum contains a significant amount of ximenynic acid,trans-11-octadecen-9-ynoic acid, a long-chain acetylenic fatty acid, as a major component (34%). The identity oftrans-ximenynic acid was confirmed after isolation by ultraviolet, infrared, and nuclear magnetic resonance (NMR) (1H- and13C-) spectroscopy and by gas chromatography/mass spectrometry (GC/MS). Thecis isomer of ximenynic acid was also found (<1%) in some samples. Thecis andtrans isomers were characterized by GC/MS comparison of their methyl esters and 4,4-dimethyloxazoline derivatives.

Key Words

4,4-Dimethyloxazoline fatty acid methyl ester gas chromatography isomers sandalwood (Santalum spicatumximenynic acid 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Hatt, H.A., and R. Schoenfeld, Some Seed Fats of theSantalaceae Family,J. Sci. Food. Agric. 7: 130–133 (1956).CrossRefGoogle Scholar
  2. 2.
    Miller, R.W., D. Weisleder, R.D. Plattner, and C.R. Smith,cis-Enediyne Chromophore of Isano Oil,Lipids 12: 669–675 (1977).Google Scholar
  3. 3.
    Spitzer, V., F. Marx, J.G.S. Maia, and K. Pfeilsticker,Curupira tefeesis II. Occurrence of Acetylenic Fatty Acids,Fat Sci. Technol. 5: 169–174 (1991).Google Scholar
  4. 4.
    Zhang, J.Y., Q.T. Yu, B.N. Liu, and Z.H. Hung, Chemical Modification in Mass Spectrometry IV. 2-Alkenyl-4,4-Dimethyloxazolines as Derivatives for the Double-Bond Location of Long-Chain Olefinic Acids,Biomed. Environ. Mass Spectrom. 15: 33–44 (1988).CrossRefGoogle Scholar
  5. 5.
    Zhang, J.Y., X.J. Yu, H.Y. Wang, B.N. Liu, Q.T. Yu, and Z.H. Hung, Location of Triple Bonds in the Fatty Acids from the Kernel Oil ofPyrularia edulis by GC-MS of their 4,4-Dimethyloxazolines Derivatives,J. Am. Oil Chem. Soc. 61: 256–259 (1989).Google Scholar
  6. 6.
    Liebich, H.M., N. Schmieder, H.G. Wahl, and J. Woll, Separation and Identification of Unsaturated Fatty Acid Isomers in Blood Serum and Therapeutic Oil Preparation in the Form of Their Oxazoline Derivatives by GC-MS,J. High Resolut. Chromatogr. 17: 519–521 (1994).CrossRefGoogle Scholar
  7. 7.
    Christie, W.W.,Gas Chromatography and Lipids, The Oily Press, Ayr, 1989, pp. 64–84.Google Scholar
  8. 8.
    Hatt, H.H., and A.Z. Szumer, The Presence of an Acetylenic Acid in the Seed Fat of Plants of the Santalaceae Family,Chem. Ind. 31: 962–963 (1954).Google Scholar
  9. 9.
    Gunstone, F.D., and W.C. Russell, Fatty Acids. Part III. The Constitution and Properties of Santalbic Acid,J. Chem. Soc. 3782–3787 (1955).Google Scholar
  10. 10.
    Kleiman, R., M.B. Bohannon, F.D. Gunstone, and J.A. Barve, Mass Spectra of Acetylenic Fatty Acid Methyl Esters and Derivatives,Lipids 11: 599–603 (1976).Google Scholar
  11. 11.
    Murphy, R.C.,Handbook of Lipid Research 7: Mass Spectrometry of Lipids, Plenum, New York, 1993, pp. 71–130.Google Scholar
  12. 12.
    Vickery, J.R., F.B. Whitfield, G.L. Ford, and B.H. Kennett, Ximenynic Acid inSantalum obtusifolium Seed Oil,J. Am. Oil Chem. Soc. 61: 890–891 (1984).Google Scholar
  13. 13.
    Nakanishi, K., and P.H. Solomon,Infrared Absorption Spectroscopy, 2nd edn, Holden-Day, Inc, Oakland, 1977, pp. 1–23.Google Scholar
  14. 14.
    Jackman, L.M., and S. Sternhell, inApplications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, edited by D.H.R. Barton and W. Doering, Pergamon Press, London, 1969, pp. 184–187.Google Scholar
  15. 15.
    Levy, G.C., and G.L. Nelson,Carbon 13 Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience, New York, 1972, pp. 59–60, 71–75.Google Scholar

Copyright information

© AOCS Press 1996

Authors and Affiliations

  • Yandi D. Liu
    • 2
  • Robert B. Longmore
    • 2
  • John E. D. Fox
    • 1
  1. 1.School of Environmental BiologyCurtin University of TechnologyPerthAustralia
  2. 2.School of PharmacyCurtin University of TechnologyPerth

Personalised recommendations