Route of decomposition of thiomersal (thimerosal)

The route of formation and identification of the principal degradation products of thimerosal (thiomersal) has been undertaken. The initial oxidation to dithiosalicylic acid is followed by cleavage of the disulphide bond of the dithiosalicylic acid by the ethylmercuric ion to reform 1.5 mol of thimerosal with concurrent oxidation to form 0.5 mol of 2-sulfinobenzoic acid for each mole of dithiosalicylic acid. In the presence of copper ions 2-sulfobenzoic acid was also formed. A mechanism has been proposed which accounts for the stoichiometry of the cleavage reaction observed and the significance of the reaction is discussed.