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Chemical Compound Review:

isovanilin 3-hydroxy-4-methoxy- benzaldehyde

Synonyms: ISOVANILLIN, Isovanilline, iso-Vanillin, PubChem7770, AGN-PC-00KE3V, ...

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High impact information on NSC82996

Incubations were also performed with specific inhibitors of each enzyme (isovanillin for aldehyde oxidase, allopurinol for xanthine oxidase, and disulfiram for aldehyde dehydrogenase) to determine the relative contribution of each enzyme in the oxidation of these aldehydes [1].
In contrast, isovanillin was rapidly catalyzed to isovanillic acid by guinea pig liver aldehyde dehydrogenase activity [2].
Thus the contribution of xanthine oxidase to isovanillin oxidation in guinea pig is very low [2].
This pathway was sensitive to inhibition with isovanillin suggesting that the enzyme responsible was aldehyde oxidase [3].
The reaction of 3,4-dihydroxybenzaldehyde (LH2) and dimethylsulfate (DMS) to form the m- and p-O-methylated products (vanillin and isovanillin, respectively) in aqueous 2-(N-morpholino)ethane sulfonate buffer was studied kinetically [4].

Associations of NSC82996 with other chemical compounds

Under these conditions, vanillin was rapidly oxidized by aldehyde oxidase, isovanillin was predominantly metabolized by aldehyde dehydrogenase activity, and protocatechuic aldehyde was slowly oxidized, possibly by all three enzymes [1].

References

Contribution of aldehyde oxidase, xanthine oxidase, and aldehyde dehydrogenase on the oxidation of aromatic aldehydes. Panoutsopoulos, G.I., Kouretas, D., Beedham, C. Chem. Res. Toxicol. (2004) [Pubmed]
Metabolism of isovanillin by aldehyde oxidase, xanthine oxidase, aldehyde dehydrogenase and liver slices. Panoutsopoulos, G.I., Beedham, C. Pharmacology (2005) [Pubmed]
Pharmacokinetics of the novel, high-affinity and selective dopamine D3 receptor antagonist SB-277011 in rat, dog and monkey: in vitro/in vivo correlation and the role of aldehyde oxidase. Austin, N.E., Baldwin, S.J., Cutler, L., Deeks, N., Kelly, P.J., Nash, M., Shardlow, C.E., Stemp, G., Thewlis, K., Ayrton, A., Jeffrey, P. Xenobiotica (2001) [Pubmed]
A chemical model of catechol-O-methyltransferase. Methylation of 3,4-dihydroxybenzaldehyde in aqueous solution. Sugata, S., Ishihara, S., Watanabe, Y., Nagata, Y., Matsushima, Y. Chem. Pharm. Bull. (1989) [Pubmed]

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