ARS | Publication request: Synthesis of novel castor oil phosphonates

Submitted to: American Chemical Society National Meeting
Publication Type: Abstract Only
Publication Acceptance Date: December 16, 2011
Publication Date: March 25, 2012
Citation: Cermak, S.C., Cermak, D.M., Fayer, E.L., Hart, M.M., Coley, C.L., Deppe, A.B., Durham, A.L. 2012. Synthesis of novel castor oil phosphonates. American Chemical Society National Meeting. AGFD 170.

Technical Abstract: Castor oil has served as a versatile hydroxy fatty acid (HFA); its principle component, ricinoleic acid, can be isolated from castor oil and has been modified extensively for a number of applications. Additionally, phosphonates and their corresponding phosphonic acids are a functional moiety that has been shown to display a wide variety of biological and synthetic applications: alpha-hydroxy phosphonates as enzyme inhibitors, pesticides, antibiotics, and anti-cancer theraputics; bisphosphonates as osteoporosis therapeutics; and vinyl phosphonates as a versatile synthetic building block. We are interested in combining these two functionalities—HFAs modified to produce phosphonates and their corresponding phosphonic acids—to produce a novel family of phosphorus-containing ricinoleic acid derivatives. We have accomplished the synthesis of two series of phosphonates based on ricinoleic acid. The results of these syntheses will be presented.