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Novel α-hydroxy phosphonic acids via castor oil
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Hydroxy fatty acids (HFAs) have found a number of uses in today's market, with uses ranging from materials to pharmaceuticals. Castor oil has served as a source of a versatile HFA; its principle component, ricinoleic acid, can be isolated from castor oil and has been modified extensively for a number of applications. Additionally, α-hydroxy phosphonates and their corresponding phosphonic acids are a functional moiety that have been shown to display a wide variety of biological activities, as enzyme inhibitors, pesticides, antibiotics and anti-cancer therapeutics. We were interested in combining these two functionalities, HFAs modified to produce α-hydroxy phosphonates and phosphonic acids, as potentially biologically active molecules. We have accomplished the synthesis of two families of α-hydroxy phosphonic acids based on ricinoleic acid: a family that retains the cis alkene found in ricinoleic acid to produce an unsaturated α-hydroxy phosphonic acid and one where the alkene has undergone hydrogenation to produce a saturated α-hydroxy phosphonic acid. These compounds have been produced in high yields and high purity, and the synthesis of these compounds is reported in this manuscript.
Cermak, Diana M.
Cermak, Steven C.
Deppe, Amy B.
Durham, Amber L.
Industrial crops and products 2012 May, v. 37, no. 1
Journal Articles, USDA Authors, Peer-Reviewed
Works produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted.
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