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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 #316442

Title: Progress towards the synthesis of lesquerella- and castor-based bisphosphonates

item CERMAK, DIANA - Knox College
item HENRY, SHANNON - Knox College
item FAYER, EFFRAT - Knox College
item COLEY, CHELSEA - Knox College
item Cermak, Steven - Steve

Submitted to: Pacifichem Symposium
Publication Type: Abstract Only
Publication Acceptance Date: 5/27/2015
Publication Date: 12/15/2015
Citation: Cermak, D.M., Henry, S., Fayer, E.L., Coley, C.L., Cermak, S.C. 2015. Progress towards the synthesis of lesquerella- and castor-based bisphosphonates [abstract]. Pacifichem 2015 - The International Chemical Congress of Pacific Basin Societies, December 15-20, 2015, Honolulu, HI. ORGN 533.

Interpretive Summary:

Technical Abstract: Lesquerella (Lesquerella fendleri) is a crop grown in the southwestern U.S. and has proven to be a useful U.S.-based source of hydroxy fatty acid (HFA). The lesquerella seed is high in oil content (~30%), of which the principal component of lesquerella oil is lesquerolic acid (55%), a C20 HFA. Lesquerolic acid is a potential domestic alternative to castor oil’s ricinoleic acid, a C18 HFA, which is not produced in the U.S. due to toxic properties of the castor bean. It has also been shown that phosphonates and their corresponding phosphonic acids are functional moieties that display a wide variety of biological and synthetic applications. In particular, bisphosphonates have found wide use as osteoporosis therapeutics as they bind Ca2+ and are known to increase bone density. We are interested in combining these two characteristics—naturally-occurring HFAs modified to produce bisphosphonates and their corresponding phosphonic acids—to produce a novel family of phosphorus-containing lesquerolic and ricinoleic acid derivatives. The results of these syntheses will be presented.