Mina S. Dasari, Kristy M. Richards, Mikaela L. Alt, Clark F. P. Crawford, Amanda Schleiden, Jai Ingram, Abdel Aziz Amadou Hamidou, Angela Williams, and Patricia A. Chernovitz
Chemistry Department, Park University, Parkville, MO 64152
Rensheng Luo
Department of Chemistry and Biochemistry, University of Missouri–St. Louis, MO 63121
Grace Y. Sun
Biochemistry Department, University of Missouri, Columbia, MO 65212
Ron Luchtefeld
Total Diet and Pesticide Research Center, U. S. Food and Drug Administration, Lenexa, KS 66214
Robert E. Smith
Chemistry Department, Park University, and Total Diet and Pesticide Research Center, U. S. Food and Drug Administration, Lenexa, KS 66214
Diapocynin (5,5′-dehydrodiacetovanillone) was synthesized by oxidative coupling of apocynin (acetovanillone, or 4-hydroxy-3-methoxyacetophenone). Diapocynin is a metabolite of apocynin, which has anti-inflammatory and anti-oxidative properties. The oxidizing agent was an in situ generated sulfate radical, produced by adding iron(II) sulfate and sodium peoxydisulfate to apocynin in boiling water. The diapocynin product was analyzed by FTIR, 1H NMR, and negative ion atmospheric pressure chemical ionization (APCI) LCMS. To minimize the quantity of triapocynin impurity, the reaction was stopped after five minutes. The product was re-dissolved in aqueous ammonia and re-precipitated with aqueous HCl. Small quantities of unreacted apocynin were removed by washing the product three times with boiling water. The FTIR spectrum was similar to that of apocynin, except in the fingerprint region. The 1H NMR indicated that one hydrogen was lost from each molecule of apocynin that reacted. The LC–MS indicated the presence of a [M-H-] ion with m/z = 329.2 amu, consistent with a molar mass of 330.2 for diapocynin.
Supplement
Additional experimental details; MS and UV spectra of diapocynin; Structures of diapocynin and apocynin generated by Spartan
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