Advertisement

Lipids

, Volume 5, Issue 10, pp 812–817 | Cite as

Cyanolipids ofCardiospermum halicacabum L. and other sapindaceous seed oils

  • K. L. Mikolajczak
  • C. R. SmithJr.
  • L. W. Tjarks
Article

Abstract

A number of sapindaceous seed oils have been investigated with respect to their cyanolipid constituents. All but one of the oils have this new class of lipids in amounts ranging from 13% to 55%. These cyanolipids are of four different types, but all consist of long-chain fatty acids esterified with an unsaturated isoprenoid hydroxy- or dihydroxynitrile. The large amounts of C20 acids usually found in these oils indicate an appreciable cyanolipid content because such acids are preferentially incorporated in nitrile-containing fractions.Cardiospermum halicacabum L. seed oil was shown to contain 49% of a diester having two fatty acid moieties esterified with 1-cyano-2-hydroxymethylprop-2-ene-1-ol and 6% of another diester derived from 1-cyano-2-hydroxymethylprop-1-ene-3-ol. Treatment of the latter diester with methanolic hydrogen chloride produces methyl 4,4-dimethoxy-3-(methoxymethyl) butyrate from the dihydroxynitrile moiety.

Keywords

Cyano Diester Preparative Thin Layer Chromatographic Glyceryl Ether Fatty Acid Moiety 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Rosenthaler, L., Schweiz. Apoth.-Ztg. 58:17–20 (1920); Chem. Abstr. 14:556 (1920).Google Scholar
  2. 2.
    Sen-Gupta, N.N., J. Soc. Chem. Ind. 39:88–91T (1920); Chem. Abstr. 14:2011 (1920).Google Scholar
  3. 3.
    Kartha, A.R.S., and R. Narayanan, JAOCS 44:350–353 (1967).Google Scholar
  4. 4.
    Kundu, M.K., and C. Bandyopadhyay, Ibid. 46:23–27 (1969).Google Scholar
  5. 5.
    Kasbeker, M.G., and N.V. Bringi, Ibid. 46:183 (1969).Google Scholar
  6. 6.
    Kundu, M.K., J. Chromatogr. 41:276–278 (1969).CrossRefGoogle Scholar
  7. 7.
    Mikolajczak, K.L., D.S. Seigler, C.R. Smith, Jr., I.A. Wolff and R.B. Bates, Lipids 4:617–619 (1969).PubMedGoogle Scholar
  8. 8.
    Seigler, D.S., K.L. Mikolajczak, C.R. Smith, Jr., I.A. Wolff and R.B. Bates, Chem. Phys. Lipids 4:147–161 (1970).CrossRefGoogle Scholar
  9. 9.
    Mikolajczak, K.L., C.R. Smith, Jr. and L.W. Tjarks, Biochim. Biophys. Acta 210:306–314 (1970).PubMedGoogle Scholar
  10. 10.
    Mikolajczak, K.L., C.R. Smith, Jr. and L.W. Tjarks, Lipids, in press.Google Scholar
  11. 11.
    Seigler, D.S., F. Seaman and T.J. Mabry, Phytochemistry, in press.Google Scholar
  12. 12.
    Hopkins, C.Y., D.F. Ewing and M.J. Chisholm, Ibid. 7:619–624 (1968).CrossRefGoogle Scholar
  13. 13.
    Miwa, T.K., K.L. Mikolajczak, F.R. Earle and I.A. Wolff, Anal. Chem. 32:1739–1742 (1960).CrossRefGoogle Scholar
  14. 14.
    Hopkins, C.Y., and R. Swingle, Lipids 2:258–260 (1967).Google Scholar
  15. 15.
    Kleiman, R., F.R. Earle and I.A. Wolff, Ibid. 4:317–320 (1969).PubMedGoogle Scholar
  16. 16.
    Bellamy, L.J. “The Infrared Spectra of Complex Molecules,” John Wiley & Sons, Inc., New York, 1956, p. 225.Google Scholar
  17. 17.
    Butler, G.W., and B.G. Butler, Nature 187:780–781 (1960).CrossRefGoogle Scholar
  18. 18.
    Butler, G.W., and E.E. Conn, J. Biol. Chem. 239:1674–1679 (1964).PubMedGoogle Scholar

Copyright information

© American Oil Chemists’ Society 1969

Authors and Affiliations

  • K. L. Mikolajczak
    • 1
  • C. R. SmithJr.
    • 1
  • L. W. Tjarks
    • 1
  1. 1.Northern Regional Research LaboratoryPeoria

Personalised recommendations