The Osage orange, discovered by Lewis and Clark in 1804, has been used in folk medicine and attracts interest of organic chemistry students. Two isoflavones, osajin and pomiferin, comprise ~7 % of the mass of the dried fruit and differ by the presence of a single oxygen atom present in pomiferin, giving pomiferin much higher anti-oxidant properties. The compounds were separated using a column chromatography cartridge containing basic alumina. About 100 mg of each compound were recovered from the solvent extract of the fruit. The >98% purity of the osajin and pomiferin fractions was assessed by NMR. The extraction, separation and purity confirmation was achieved in a single laboratory period. Laboratory exercises to demonstrate the anti-oxidant activity of osajin and pomiferin can be performed in a separate laboratory session. The protocol was tested in the classroom. The complete exercise was used for community college students in an transformative learning experience.

Rapid chromatographic separation of osajin and pomiferin in the organic chemistry laboratory course

243rd National Meeting (2012)

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