Abstract
Koelreuteria paniculata Laxm. (Sapindaceae) seed oil is a mixture of cyanolipids (42%) and ordinary triglycerides. The cyanolipid portion contains two classes of components. One of these (25% of the oil) is a mixture of diesters composed of two fatty acid moieties (predominantly C18 and C20 monoenoic) esterified with an unsaturated five-carbon dihydroxynitrile (1-cyano-2-hydroxymethylprop-1-ene-3-ol). The other class (17% of the oil) consists of cyanolipids having one fatty acid moiety (predominantly C20 monoenoic) esterified with 1-cyano-2-methylprop-1-ene-3-ol. Monoesters based on this same hydroxynitrile were previously isolated fromStocksia brahuica seed oil and characterized. Hydrogenation of the diesters was accompanied by varying degrees of hydrogenolysis of the ester groups. The hydrogenated diester was reduced with lithium borohydride and the dihydroxynitrile portion was isolated. Acetolysis of the hydrogenated diester in glacial acetic acid with sulfuric acid catalyst yielded an acetylated γ-lactone. The double bond of the dihydroxynitrile moiety in the diester does not react with bromine in carbon tetrachloride.
Similar content being viewed by others
References
Rosenthaler, L., Schweiz. Apoth. Ztg. 58:17–20 (1920); Chem. Abstr. 14:556 (1920).
Sen-Gupta, N.N., J. Soc. Chem. Ind. 39:88–91T (1920); Chem. Abstr. 14:2011 (1920).
Kundu, M.K., and C. Bandyopadhyay, JAOCS 46:23–27 (1969).
Kasbeker, M.G., and N.V. Bringi, Ibid. 46:183 (1969).
Mikolajczak, K.L., D.S. Seigler, C.R. Smith, I.A. Wolff and R.B. Bates, Lipids 4:617–618 (1969).
Seigler, D.S., K.L. Mikolajczak, C.R. Smith, I.A. Wolff and R.B. Bates, Chem. Phys. Lipids 4:147–161 (1970).
Mikolajczak, K.L., C.R. Smith and L.W. Tjarks, Biochim. Biophys. Acta 210:306–314 (1970).
Miwa, T.K., K.L. Mikolajczak, F.R. Earle and I.A. Wolff, Anal. Chem. 32:1739–1742 (1960).
Official Methods of Analysis of the Association of Official Agricultural Chemists, 9th Edition, 1960, p. 293.
Cannon, G.W., A.A. Santilli and P. Shenian, J. Amer. Chem. Soc. 81:1660–1666 (1959).
Kitson, R.E., and N.E. Griffith, Anal. Chem. 24:334–337 (1952).
Bellamy, L.J., “The Infrared Spectra of Complex Molecules,” John Wiley & Sons, Inc., New York, 1956, p. 212.
Nystrom, R.F., S.W. Chaikin and W.G. Brown, J. Amer. Chem. Soc. 71:3245–3246 (1949).
Brown, H.C., “Hydroboration,” W.A. Benjamin, Inc., New York, 1962, p. 253.
Williams, D.M., and T.C. James, J. Chem. Soc. 1928:343–347.
Robertson, P.W., N.T. Clare, K.J. McNaught and G.W. Paul, Ibid. J. Chem. Soc., 1937:335–343.
Nozaki, K., and R.A. Ogg, Jr., J. Amer. Chem. Soc. 64:697–704 (1942).
Hopkins, C.Y., D.F. Ewing and M.J. Chisholm, Phytochemistry 7:619–624 (1968).
Hopkins, C.Y., and R. Swingle, Lipids 2:258–260 (1967).
Author information
Authors and Affiliations
Additional information
No. Utiliz. Res. Dev. Div., ARS, USDA.
About this article
Cite this article
Mikolajczak, K.L., Smith, C.R. & Tjarks, L.W. Cyanolipids ofKoelreuteria paniculata Laxm. seed oil. Lipids 5, 672–677 (1970). https://doi.org/10.1007/BF02531433
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02531433