Cyanolipids of Cardiospermum halicacabum L. and other sapindaceous seed oils

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. © 1969 American Oil Chemists' Society.