Strain A81 of
Nocardia corallina
hydroxylates or demethylates
p
-anisic acid to
p
-hydroxybenzoic acid and isovanillic acid. It demethylates veratric acid to a mixture of vanillic and isovanillic acids. These are both demethylated to protocatechuic acid, which undergoes ring cleavage to afford β-carboxy-
cis-cis
-muconic acid. The intermediacy of protocatechuic acid in the catabolic pathway of veratric acid was confirmed by blocking ring cleavage with an additional substituent in the ring: 5-chlorovanillic acid was demethylated to 5-chloro-protocatechuic acid, which accumulated. Chloro substituents in the ring of other methoxylated benzoic acids also arrested their normal metabolism by the
Nocardia
: an
ortho
-chloro substituent thwarted both demethylation and ring-opening.
ortho
-Hydroxylation of
p
-methoxybenzoic acid to isovanillic acid was unaffected by a chlorine
ortho
to the methoxyl group. Washed whole cells of veratric acid-grown
N. corallina
A81 produced no detected structural changes in an isolated lignin. The implications of this observation are discussed.