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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 #277956

Title: Synthesis of alpha-hydroxyphosphonic acids from Lesquerella oil

item HART, MARGARET - Knox College
item CERMAK, DIANA - Knox College
item FAYER, EFFRAT - Knox College
item Cermak, Steven - Steve

Submitted to: American Chemical Society National Meeting
Publication Type: Abstract Only
Publication Acceptance Date: 1/30/2012
Publication Date: 3/25/2012
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.

Interpretive Summary:

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.