ARS | Publication request: Synthesis of alpha-hydroxyphosphonic acids from Lesquerella oil

Submitted to: American Chemical Society National Meeting
Publication Type: Abstract Only
Publication Acceptance Date: January 30, 2012
Publication Date: March 25, 2012
Citation: Hart, M., Cermak, D.M., Fayer, E., Cermak, S.C. 2012. Synthesis of alpha-hydroxyphosphonic acids from Lesquerella oil. American Chemical Society National Meeting. CHED 1151.

Technical Abstract: Lesquerella oil has been a substance of growing chemical interest, due to the ease with which it is produced and its similarity in structure to castor oil. The primary fatty acid in Lesquerella oil, lesquerolic acid, is very similar to the principal component of castor oil, ricinoleic acid, and may find use as a US-based source of fatty acid. The carboxyl moiety in lesquerolic acid can easily be chemically modified and will be the location of alpha-hydroxyphosphonic acid formation, a functional group that has been found in antibacterial drugs, enzyme inhibitors, antibiotics, antiviral agents, and anticancer agents. The alkene in the middle of the chain will allow the creation of two different product families: one saturated and one unsaturated. Progress and limitations to the synthesis of the final product, as well as suggested modifications will be presented.