Nonylphenol (NP) and the 9-mole ethoxylate of nonylphenol (NPE9) were synthesized with a uniform radioactive (14)C label in the aromatic ring. The [(14)C]NP isomer distribution and [(14)C]NPE9 oligomer distribution closely matched that of commercial NPE9. Biodegradation of [(14)C]NPE9 was examined under conditions simulating a river water environment, and changes in the oligomer distribution and mineralization to (14)CO(2) were monitored for 128 days. Over 40% of the [(14)C]NPE aromatic ring carbon was converted to (14)CO(2) and another 21% was incorporated into the biomass. Primary degradation of NPE (conversion to metabolites other than NP, NPE ethoxylates, and NPE carboxylates) was estimated to be 87-97%. NP was a minor metabolite, accounting for less than 0.4% of the initial NPE. These studies demonstrate that the phenolic ring of NPE is opened, metabolized, and mineralized in the aquatic environment.