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The metabolic pathway of butylated hydroxytoluene (BHT) to the ring-oxygenated metabolites 2,6-di-tert-butylhydroquinone (BHQ) and 2,6-di-tert-butyl-p-benzoquinone (BBQ) was examined in rats. After intraperitoneal administration of 3,5-di-tert-butyl-4-hydroxybenzoic acid (BHT-acid), which had been regarded as one of the major metabolic end-products of BHT, 2,6-di-tert-butylphenol (DBP) and BBQ were identified in the feces by gas chromatography and gas chromatography-mass spectrometry (GC-MS). The biliary excretion of BBQ, BHQ glucuronide and BHT-acid glucuronide was also confirmed by GC-MS and high-performance liquid chromatography methods. The excretion rate of BHQ glucuronide for 24h after dosing with BHT-acid was about 9-fold higher than that after dosing with BHT. In addition, the formation of BBQ was confirmed in the urine after dosing with DBP. These results suggest that BHT is metabolized to BHQ and BBQ through DBP formed by decarboxylation of BHT-acid.
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