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Chemical Compound Review:

VERATRIC ACID 3,4-dimethoxybenzoic acid

Synonyms: PubChem13788, SPECTRUM212140, CHEMBL118903, SureCN114848, NSC-7721, ...

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Disease relevance of NSC 7721

The aim of this study was to investigate the correlation between veratrate degradation, veratric acid concentration and cell density in Rhodococcus erythropolis cultures [1].
Substrate-induction of veratric acid O-demethylase in Nocardia sp [2].
Expression of the vanAB genes in Streptomyces lividans 1326 resulted in in vivo demethylation of veratric acid to vanillic acid [3].

High impact information on NSC 7721

The major product of the LMC oxidation was 1-(3,4-dimethoxyphenyl)-1-oxo-2-(2-methoxyphenoxy)-3-hydroxypropane; in addition, small amounts of 3,4-dimethoxybenzaldehyde (veratraldehyde) and 3,4-dimethoxybenzoic (veratric) acid were detected [4].
In this work, veratric acid (3,4-dimethoxybenzoic acid), which has fluorescence characteristics (lambda ex = 290 nm, lambda em = 350 nm) around the wavelength of native fluorescence of melatonin (lambda ex = 285 nm, lambda em = 345 nm), was used as an internal standard [5].
In two fatalities involving possible therapeutic use, no mebeverine was detected, but mebeverine-alcohol (6.9 and 5.4 mg/L) and veratric acid (13.7 and 41.8 mg/L) were found by gas chromatography-mass spectrometry and high-performance liquid chromatography-diode-array detection (HPLC-DAD) and measured by HPLC-DAD [6].
Mebeverine, mebeverine-alcohol, and veratric acid concentrations should be measured in the blood/serum to assist interpretation; however, because of rapid metabolism/instability, mebeverine itself is rarely detected [6].
MB is metabolized via ester hydrolysis to MB alcohol (MB-OH) and veratric acid [7].

Chemical compound and disease context of NSC 7721

Nocardia sp. demethylates veratric acid to vanillic and isovanillic acids, and subsequently to protocatechuic acid [2].

Biological context of NSC 7721

Relationship of demethylation processes to veratric acid concentration and cell density in cultures of Rhodococcus erythropolis [1].

Associations of NSC 7721 with other chemical compounds

Pyridostigmine pretreatment mediated a significantly higher peak concentration of veratric acid, the acid moiety resulting from hydrolysis of mebeverine [8].

References

Relationship of demethylation processes to veratric acid concentration and cell density in cultures of Rhodococcus erythropolis. Paździoch-Czochra, M., Malarczyk, E., Sielewiesiuk, J. Cell Biol. Int. (2003) [Pubmed]
Substrate-induction of veratric acid O-demethylase in Nocardia sp. Malarczyk, E. Acta Biochim. Pol. (1984) [Pubmed]
Molecular cloning of streptomyces genes encoding vanillate demethylase. Nishimura, M., Ishiyama, D., Davies, J. Biosci. Biotechnol. Biochem. (2006) [Pubmed]
Involvement of lipid peroxidation in the degradation of a non-phenolic lignin model compound by manganese peroxidase of the litter-decomposing fungus Stropharia coronilla. Kapich, A.N., Steffen, K.T., Hofrichter, M., Hatakka, A. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
Variation of melatonin and serotonin content in rat pineal gland with sex and oestrous phase difference determined by high-performance liquid chromatography with fluorimetric detection. Wakabayashi, H., Shimada, K., Aizawa, Y. J. Chromatogr. (1986) [Pubmed]
Investigative implications of the instability and metabolism of mebeverine. Elliott, S., Burgess, V. Journal of analytical toxicology. (2006) [Pubmed]
The antispasmodic drug mebeverine leads to positive amphetamine results by fluorescence polarization immunoassay (FPIA)--studies on the toxicological analysis of urine by FPIA and GC-MS. Kraemer, T., Wennig, R., Maurer, H.H. Journal of analytical toxicology. (2001) [Pubmed]
Lack of bioavailability of mebeverine even after pretreatment with pyridostigmine. Sommers, D.K., Snyman, J.R., van Wyk, M., Eloff, J.N. Eur. J. Clin. Pharmacol. (1997) [Pubmed]

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