The metabolism of the clinically utilized, anticoagulant warfarin [4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one] by rat liver microsomes has been investigated. The structure of a new warfarin metabolite [4-hydroxy-3-(3-oxo-1-phenyl-1-butenyl)-2H-1-benzopyran-2-one] (dehydrowarfarin) has been determined by mass spectral comparison with the chemically synthesized compound. The formation of dehydrowarfarin is catalyzed by cytochrome P-450 and is unusual in that the final product is effectively dehydrogenated warfarin.

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Three hydantoins, namely, hydantoin, 5,5-dimethylhydantoin and 5-carboxymethylidine hydantoin are released on acid-hydrolysis of HCN oligomers. These hydantoins correspond to the major amino acids released on acid-hydrolysis of HCN oligomers. Carbamyl groups present in the HCN oligomers are probably the principal precursors of these hydantoins. 5-Carboxymethylidine hydantoin is formed by the acid-catalyzed eyclization of the dicarbamyl derivative of diaminosuccinic acid. The facile rearrangement of 5-carboxymethylidine hydantoin to orotic acid in base suggests the possibility of a direct route to pyrimidines from HCN.

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