Oxidative Ring-Cleavage of Catechol in meta-Position by Superoxide

Rudolf Müller, Franz Lingens
1989 Zeitschrift für Naturforschung C - A Journal of Biosciences  
Superoxide reacts with catechol in dimethylsulfoxide to form a yellow product. The structure of this product was established by different methods. UV-spectra of the yellow compound corresponded under all circumstances to those of enzymatically produced 2-hydroxymuconic acid semialdehyde. In the presence of ammonia the product was converted to picolinic acid. The UV - spectra, the retention times in GC and HPLC and the mass spectra after methylation corresponded to those of authentic picolinic
more » ... id. Thus, the yellow reaction product was unequivocally identified as 2-hydroxymuconic acid semialdehyde. The formation of the me/a-cleavage product was only observed at low catechol concentrations (<2 mM) , at higher concentrations the product was not formed. The reaction was complete within 10 min at room temperature. Spectroscopic data suggest a first intermediate in the reaction with λmax = 804 nm, 772 nm and 660 nm.
doi:10.1515/znc-1989-3-406 fatcat:4zkrc6mp5zd6nbe56t6qra3gjq