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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 #404959
Research Project: Development of New Value-Added Processes and Products from Advancing Oilseed Crops

Location: Bio-oils Research

Title: Novel bisphosphonates via castor oil

Author
item FAYER, EFFRAT - Knox College
item ROSEN, EMILY - Knox College
item CERMAK, DIANA - Knox College
item Cermak, Steven - Steve

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/26/2023
Publication Date: 7/16/2023
Citation: Fayer, E.L., Rosen, E., Cermak, D.M., Cermak, S.C. 2023. Novel bisphosphonates via castor oil. Journal of the American Oil Chemists' Society. 100(10):803-813. https://doi.org/10.1002/aocs.12723.
DOI: https://doi.org/10.1002/aocs.12723

Interpretive Summary: In this research, we discovered that the main constituent of castor oil, ricinoleic acid, could be synthetically converted to a family of bisphosphonates, a chemical functionality that is present in many osteoporosis drugs. Bisphosphonates are most commonly used to bind calcium, which have been most commonly used for basic water purification and pharmaceutical applications. We have made a new bisphosphonate family series from the principal component of castor oil, thus expanding the functionalization and size of bisphosphonates available to the chemical community. It was found that two different types of castor oil-based bisphosphonates could be chemically synthesized in high purity in five to six steps in respective yields. These findings have the potential to widen the scope of castor oil's utility and application in industrial processes, most specifically in the pharmaceutical industry.

Technical Abstract: Hydroxy fatty acids (HFAs) have long been a staple component of feedstock oils with uses ranging from motor oils to food to pharmaceuticals. Castor oil, which contains the HFA ricinoleic acid as its principal component, is the most widely used source of HFA in the world. In addition, bisphosphonates are a functional moiety that has been shown to display a variety of industrial applications, ranging from use in water softeners to osteoporosis drugs, primarily due to their affinity for the calcium ion. We have long been interested in the modification of ricinoleic acid from castor oil to phosphorus derivatives, including a-hydroxy phosphonates and phosphonic acids, and have now accomplished the synthesis of a family of ricinoleic-derived bisphosphonates: one that retains the cis alkene found in ricinoleic acid and one where the alkene has undergone hydrogenation. These compounds have been produced in high yields and high purity and the synthesis of these compounds is reported.