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4-Hydroxy-3-methylbenzoic acid Sale

(Synonyms: 4-羟基-3-甲基苯甲酸) 目录号 : GC33656

4-Hydroxy-3-methylbenzoic acid is a normal organic acid identified in urine specimens from a healthy population.

4-Hydroxy-3-methylbenzoic acid Chemical Structure

Cas No.:499-76-3

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1g
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Sample solution is provided at 25 µL, 10mM.

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产品描述

4-Hydroxy-3-methylbenzoic acid is a normal organic acid identified in urine specimens from a healthy population.

Chemical Properties

Cas No. 499-76-3 SDF
别名 4-羟基-3-甲基苯甲酸
Canonical SMILES OC(=O)c1ccc(c(c1)C)O
分子式 C8H8O3 分子量 152.15
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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溶解性数据

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1 mM 6.5725 mL 32.8623 mL 65.7246 mL
5 mM 1.3145 mL 6.5725 mL 13.1449 mL
10 mM 0.6572 mL 3.2862 mL 6.5725 mL
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Research Update

The bacterial metabolism of 2,4-xylenol

Biochem J 1968 Dec;110(3):491-8.PMID:4387388DOI:10.1042/bj1100491.

1. Measurements of the rates of oxidation of various compounds by a fluorescent Pseudomonas indicated that metabolism of 2,4-xylenol was initiated by oxidation of the methyl group para to the hydroxyl group. 2. 4-Hydroxy-3-methylbenzoic acid was isolated as the product of oxidation of 2,4-xylenol by cells inhibited with alphaalpha'-bipyridyl. 3. 4-Hydroxyisophthalic acid accumulated at low oxygen concentrations when either 2,4-xylenol or 4-Hydroxy-3-methylbenzoic acid was oxidized by cells grown with 2,4-xylenol. 4. When supplemented with NADH, but not with NADPH, cell extracts oxidized 4-Hydroxy-3-methylbenzoic acid readily. 2-Hydroxy-5-methylbenzoic acid was not oxidized. 5. Both 4-hydroxyisophthalic acid and p-hydroxybenzoic acid were oxidized to beta-oxoadipic acid by cell extracts supplemented with either NADH or NADPH. 4,5-Dihydroxyisophthalic acid was not oxidized. 6. From measurements of oxygen consumed and carbon dioxide evolved it was concluded that protocatechuic acid is an intermediate in the conversion of 4-hydroxyisophthalic acid into beta-oxoadipic acid.

Biodegradation of dimethylphenols by bacteria with different ring-cleavage pathways of phenolic compounds

Environ Sci Pollut Res Int 2002;Spec No 1:19-26.PMID:12638744DOI:10.1007/BF02987421.

The biodegradation of 3,4, 2,4, 2,3, 2,6 and 3,5-dimethylphenol in combination with phenol and p-cresol by axenic and mixed cultures of bacteria was investigated. The strains, which degrade phenol and p-cresol through different catabolic pathways, were isolated from river water continuously polluted with phenolic compounds of leachate of oil shale semicoke ash heaps. The proper research of degradation of 2,4 and 3,4-dimethylphenol in multinutrient environments was performed. The degradation of phenolic compounds from mixtures indicated a flux of substrates into different catabolic pathways. Catechol 2,3-dioxygenase activity was induced by dimethylphenols in Pseudomonas mendocina PC1, where meta cleavage pathway was functional during the degradation of p-cresol. In the case of strains PC18 and PC24 of P. fluorescens, the degradation of p-cresol occurred via the protocatechuate ortho pathway and the key enzyme of this pathway, p-cresol methylhydroxylase, was also induced by dimethylphenols. 2,4 and 3,4-dimethylphenols were converted into the dead-end products 4-Hydroxy-3-methylbenzoic acid and 4-hydroxy-2-methylbenzoic acid. In the degradation of 3,4-dimethylphenol, the transient accumulation of 4-hydroxy-2-methylbenzaldehyde repressed the consumption of phenol from substrate mixtures. A mixed culture of strains with different catabolic types made it possible to overcome the incompatibilities at degradation of studied substrate mixtures.

The catabolism of 2,4-xylenol and p-cresol share the enzymes for the oxidation of para-methyl group in Pseudomonas putida NCIMB 9866

Appl Microbiol Biotechnol 2014 Feb;98(3):1349-56.PMID:23736872DOI:10.1007/s00253-013-5001-z.

Pseudomonas putida NCIMB 9866 utilizes p-cresol or 2,4-xylenol as a sole carbon and energy source. Enzymes catalyzing the oxidation of the para-methyl group of p-cresol have been studied in detail. However, those responsible for the oxidation of the para-methyl group in 2,4-xylenol catabolism are still not reported. In this study, real-time quantitative PCR analysis indicated pchC- and pchF-encoded p-cresol methylhydroxylase (PCMH) and pchA-encoded p-hydroxybenzaldehyde dehydrogenase (PHBDD) in p-cresol catabolism were also likely involved in the catabolism of 2,4-xylenol. Enzyme activity assays and intermediate identification indicated that the PCMH and PHBDD catalyzed the oxidations of 2,4-xylenol to 4-hydroxy-3-methylbenzaldehyde and 4-hydroxy-3-methylbenzaldehyde to 4-Hydroxy-3-methylbenzoic acid, respectively. Furthermore, the PCMH-encoding gene pchF was found to be necessary for the catabolism of 2,4-xylenol, whereas the PHBDD-encoding gene pchA was not essential for the catabolism by gene knockout and complementation. Analyses of the maximum specific growth rate (μ m) and specific activity of the gene-knockout strain to different intermediates revealed the presence of other enzyme(s) with PHBDD activity in strain 9866. However, PHBDD played a major role in the catabolism of 2,4-xylenol in contrast to the other enzyme(s).

Carboxylation of o-cresol by an anaerobic consortium under methanogenic conditions

Appl Environ Microbiol 1991 Aug;57(8):2131-4.PMID:1768084DOI:10.1128/aem.57.8.2131-2134.1991.

The metabolism of o-cresol under methanogenic conditions by an anaerobic consortium known to carboxylate phenol to benzoate was investigated. After incubation with the consortium at 29 degrees C for 59 days, o-cresol was transformed to 3-methylbenzoic acid, which was not further metabolized by the consortium. Proteose peptone in the culture medium was essential for the transformation of o-cresol. In addition, a transient compound detected in the culture was identified as 4-Hydroxy-3-methylbenzoic acid. o-Cresol-6d was transformed by the consortium to deuterated hydroxy-methylbenzoic acid and deuterated methylbenzoic acid. These results demonstrate that o-cresol is carboxylated in the para position relative to the phenolic hydroxyl group and dehydroxylated by the anaerobic consortium.

Biodegradation of phenolic compounds and their metabolites in contaminated groundwater using microbial fuel cells

Bioresour Technol 2016 Jan;200:426-34.PMID:26512868DOI:10.1016/j.biortech.2015.09.092.

This is the first study demonstrating the biodegradation of phenolic compounds and their organic metabolites in contaminated groundwater using bioelectrochemical systems (BESs). The phenols were biodegraded anaerobically via 4-hydroxybenzoic acid and 4-Hydroxy-3-methylbenzoic acid, which were retained by electromigration in the anode chamber. Oxygen, nitrate, iron(III), sulfate and the electrode were electron acceptors for biodegradation. Electro-active bacteria attached to the anode, producing electricity (~1.8mW/m(2)), while utilizing acetate as an electron donor. Electricity generation started concurrently with iron reduction; the anode was an electron acceptor as thermodynamically favorable as iron(III). Acetate removal was enhanced by 40% in the presence of the anode. However, enhanced removal of phenols occurred only for a short time. Field-scale application of BESs for in situ bioremediation requires an understanding of the regulation and kinetics of biodegradation pathways of the parent compounds to relevant metabolites, and the syntrophic interactions and carbon flow in the microbial community.