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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #274855

Title: Novel alpha-hydroxy phosphonic acids via castor oil

Author
item Cermak, Diana - Knox College
item Cermak, Steven - Steve
item Deppe, Amy
item Durham, Amber

Submitted to: Industrial Crops and Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 12/15/2011
Publication Date: 1/27/2012
Publication URL: http://handle.nal.usda.gov/10113/54033
Citation: Cermak, D.M., Cermak, S.C., Deppe, A.B., Durham, A.L. 2012. Novel alpha-hydroxy phosphonic acids via castor oil. Industrial Crops and Products. 37:394-400.

Interpretive Summary: We have investigated the synthesis of a series of potentially biologically-active molecules, alpha-hydroxy phosphonic acids, based on ricinoleic acid. These compounds have been produced in high yields and high purity, and the complete synthesis of these compounds is reported. Hydroxy fatty acids (HFAs) have found a number of uses in today’s market, with uses ranging from materials to pharmaceuticals. Castor oil, Ricinus communis, has served as a versatile HFA; its principle component, ricinoleic acid, can be isolated from castor oil and has been modified extensively for a number of applications. Alpha-hydroxy phosphonates and their corresponding phosphonic acids are a functional moiety that has been shown to display a wide variety of biological activities, as enzyme inhibitors, pesticides, antibiotics, and anti-cancer theraputics.

Technical 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 versatile HFA; its principle component, ricinoleic acid, can be isolated from castor oil and has been modified extensively for a number of applications. Additionally, alpha-hydroxy phosphonates and their corresponding phosphonic acids are a functional moiety that has been shown to display a wide variety of biological activities, as enzyme inhibitors, pesticides, antibiotics, and anti-cancer theraputics. We were interested in combining these two functionalities, HFAs modified to produce alpha-hydroxy phosphonates and phosphonic acids, as potentially biologically-active molecules. We have accomplished the synthesis of two families of alpha-hydroxy phosphonic acids based on ricinoleic acid: a family that retains the cis alkene found in ricinoleic acid to produce an unsaturated alpha-hydroxy phosphonic acid and one where the alkene has undergone hydrogenation to produce a saturated alpha-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.