Submitted to: Lipid Technology
Publication Type: Review Article
Publication Acceptance Date: November 1, 1997
Publication Date: N/A
Technical Abstract: The delta 5 unsaturation of meadowfoam lends itself to the synthesis of a wide variety of novel fatty acid derivatives. The most significant synthetic manipulation thus far has been the discovery of the cyclization of triglyceride to delta-lactone and the subsequent chemistry of this fatty acid synthon. The delta-lactone easily undergoes substitution by nucleophiles, presumably in most cases by a carboxylate stabilized carbocation. This stabilization has resulted in the synthesis of 5-hydroxy substituted esters and amides and the novel 5-alkoxy substituted esters. The delta-lactones facile conversion to 5-hydroxyeicosanoic acid, in situ, from meadowfoam oil is a previously undemonstrated reaction of unsaturated oils to hydroxy fatty acids. Lastly, novel chlorinated fatty acids derivatives such as chloroethers and 6-chloro-delta-lactones can be made inexpensively from common reagents and simple reaction conditions.