We used a recombinant yeast estrogen assay to assess the activity of 73 phenolic additives that are used as sunscreens, preservatives, disinfectants, antioxidants, flavorings, or for perfumery. Thirty-two of these compounds displayed activity: 22 with potencies relative to 17beta-estradiol, ranging from 1/3,000 to < 1/3,000,000, and 10 compounds with an impaired response that could not be directly compared with 17beta-estradiol. Forty-one compounds were inactive. The major criteria for activity appear to be the presence of an unhindered phenolic OH group in a para position and a molecular weight of 140-250 Da.

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Anodic oxidation of the dye molecules, methylene blue, acid blue 25, reactive blue 2 and reactive blue 15 in chloride solution leads to colour destruction but UV and TOC data show that the oxidation reactions do not lead to complete destruction of the organic molecules. Analysis of the anodic oxidation products of [3,7-bis (dimethylamino) phenothiazinium] chloride (methylene blue) in a chloride solution provides evidence for formation of seven neutral and two charged intermediates. The main intermediate is identi®ed by its X-ray diffraction crystal structure and accurate mass spectrometry as the novel leuco dye 4,6-dichloro-7-dimethylamino-3H-phenothiazin-3-one, C 14 H 10 Cl 2 N 2 OS (I) formed by replacement of one of the dimethylamino groups of methylene blue with oxygen accompanied by regiospeci®c chlorination of the carbocyclic systems. The mass spectra of other intermediates formed are interpreted in terms of the structure of I.