ARS | Publication request: MODIFICATION OF SIMMONDSIN AND ITS ANALOGUES

Submitted to: Industrial Crops and Products International Conference Proceedings
Publication Type: Abstract Only
Publication Acceptance Date: October 21, 1999
Publication Date: N/A

Technical Abstract: Simmondsin and its analogues, demethyl-, didemethylsimmondsins and the 2'- and 3'-simmondsin ferulates are components isolable from Jojoba (Simmondsia chinensis) seed meal. While the parent compound, simmondsin, is reported to exhibit anorexic properties, all its analogues not only lack this behavior, except the ferulates, but also have no identifiable market value. For a new industrial crop to be profitable, it is important that most of its components have unique marketable properties. Thus, the goal of this research project was to chemically functionalize demethyl- and didemethyl simmondsins, thereby imbuing them with characteristics for economic potential. A two pronged approach was carried out for converting these materials to useful compounds. The first was a selective remethylation of the 4- or 4,5-positions, respectively, of the demethylated isolates in order to regenerate simmondsin. And secondly, to modify the cyano function either reductively to generate the amine derivative of simmondsin or by an analogous pathway to the amides. In this vein, simmondsin and the demethyl analogues have been partially and exhaustively methylated, as well as acetylated to give the respective intermediates. Because of the sensitivity of the parent compound to both acidic and alkaline environments, the permethylated ether was converted to the imidates via the cyano function. The imidates were then condensed with fatty amines as substrates in the formation of simmondsin amides.