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2743115 
Journal Article 
Identification And Determination Of Glutathione And Glucuronide Conjugates Formed From Butylated Hydroxytoluene In Rats 
Tajima, K; Yamamoto, K; Mizutani, T 
1983 
Yes 
Chemical and Pharmaceutical Bulletin
ISSN: 0009-2363
EISSN: 1347-5223 
NIOSH/00161101 
31 
10 
3671-3677 
English 
6671228 
WOS:A1983RR94600040 
Glutathione and glucuronide conjugates formed from 3,5-di-tert-butyl-4-hydroxytoluene (128370) (BHT) were studied in rats. Bile was collected for 24 hours from cannulated rats after intraperitoneal injection of 400 milligrams per kilogram BHT. After extraction, three fractions were separated by high performance liquid chromatography; each fraction contained a metabolite, M1, M2, and M3. After identification, the biliary excretion rates of the metabolites were determined. M1 and M2 were identified by gas chromatography/mass spectrometry as 3,5-di-tert-butylhydroquinone-glucuronide (BHQ/glucuronide) and 3,5-di-tert-butyl-4-hydroxybenzoic-acid-glucuronide (BHT/acid-glucuronide), respectively. M3 was identified by radiolabeled carbon nuclear magnetic resonance and field desorption mass spectrometry as S-(3,5-di-tert-butyl-4-hydroxybenzyl)-glutathione (BHT/glutathione). The biliary excretion rates of BHT/glutathione and BHQ/glucuronide in 24 hours were 3.5 and 1.6 percent, respectively, of the administered dose. The authors suggest that the metabolic reaction forming BHT/glutathione involves the reaction of BHT/quinone/methide with glutathione, and may play a significant role in preventing the toxicity of BHT. 
13C-NMR; BHT glutathione conjugate; butylated hydroxytoluene (BHT); field desorption mass spectrometry; GC-MS- rat bile; HPLC