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Novel α-hydroxy phosphonic acids via castor oil

Permanent URL:
http://handle.nal.usda.gov/10113/54033
File:
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Abstract:
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.
Author(s):
Cermak, Diana M. , Cermak, Steven C. , Deppe, Amy B. , Durham, Amber L.
Subject(s):
antibiotics , antineoplastic agents , bioactive properties , castor oil , enzyme inhibitors , hydrogenation , pesticides , phosphonates , purity , ricinoleic acid , therapeutics
Note:
Includes references
Source:
Industrial crops and products 2012 May, v. 37, no. 1
Language:
English
Year:
2012
Collection:
Journal Articles, USDA Authors, Peer-Reviewed
Rights:
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.