Synthesis and Evaluation in Vitro of 4-Acetamidophenyl Phosphate

Abstract

4-Acetamidophenyl phosphate was synthesized by a phosphorylation procedure with polyphosphoric acid to examine its properties as a prodrug of acetaminophen. Separation of the ester from the phosphorylation mixture was carried out by precipitation with organic solvents. 4-Acetamidophenyl phosphate was soluble in water, was practically tasteless, and was quickly hydrolyzed to acetaminophen by alkaline phosphatase at 37°. The ester was stable in aqueous solution at neutral and acidic pH at 37°.