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Additional info for Biochemistry of Glucuronic Acid
Following administration of salicylates, patients suf fering from rheumatic fever excreted conjugated glucuronic acid in amounts within the range observed for normal subjects, although the output of salicyluric was less and that of gentisic acid much larger than normal (194). Quick (351) found that m-hydroxybenzoic acid is excreted by man largely in combination with glycine, but a small amount is conjugated with glu curonic acid. The amount of glucuronoside formed from p-hydroxybenzoic acid was extremely small in man.
When fed to rabbits, p-dimethylaminobenzaldehyde not only was oxidized to the corresponding acid, p-dimethylaminobenzoic acid being isolated from the urine as a glucuronoside, but was also partially demethylated. There was evidence that a glucuronic acid conjugate of p-monomethylaminobenzoic acid also was formed (186). Dogs excrete p-hydroxybenzaldehyde (XLVI) as p-glucuronosidobenzoyl glucuronoside, p-hydroxyhippuric acid and possibly free p-hydroxybenzoic acid (67, 351). In the case of rabbits, however, p-glucuronosidobenzaldehyde has been isolated from the urine as the 2,4-dinitrophenylhydrazone and it appeared probable that conjugation of the phenolic hydroxyl with glucuronic acid preceded oxidation of the aldehyde group (147).
The metabolism of 3,4-benzpyrene, a hydrocarbon of extremely high carcinogenic activity which has been isolated from coal tar, is by no means clear. However, one metabolic product has been isolated in crystalline form from bile (52) and identified as 8-hydroxy-3,4-benzpyrene (22) (XXXV). 3,4-Benzpyrene-5,8-quinone (XXXVI) was isolated from the faeces òf rats receiving 3,4-benzpyrene (22). Other hydroxy compounds, some phenolic and others alcoholic in nature, have been suggested as intermediary metabolites of benzpyrene (434).