ARS | Publication request: MODIFICATION OF SIMMONDSIN ANALOGUES II

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 16, 2001
Publication Date: N/A

Technical Abstract: Simmondsin [2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl -D-glucopyranoside] and its analogues are components isolatable from defatted jojoba (Simmondsia chinensis) seed meal. Whereas simmondsin and its ferulate isomers exhibit various degrees of food-intake reduction properties and are currently in feeding trials, the three demethyl-4,5-simmondsin analogues (4-demethyl-, 5-demethyl- and 4,5-didemethyl-) have no known use. In a continuing effort to maximize utilization of simmondsins, we have explored epoxidation of the carbon-carbon double bond of the cyclitol side-chain of the demethylated compounds to generate the oxirane intermediates which are amenable to formation of long chain carboxylic esters. Additionally, reduction of the nitrile function of the side-chain to the amine has allowed formation of fatty carboxamides of simmondsin.