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Chemical Compound Review:

CHEMBL663 3-phenoxybenzoic acid

Synonyms: PubChem14424, SureCN128732, ACMC-1CJQX, Enamine_000396, CBDivE_003261, ...

Bast, G.E. et al., Halden, R.U. et al., Leng, G. et al., Haselden, J.N. et al., Sun, H. et al., et al.

Leng, Kühn, Idel,

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Disease relevance of m-Phenoxybenzoic acid

Degradation of 3-phenoxybenzoic acid in soil by Pseudomonas pseudoalcaligenes POB310(pPOB) and two modified Pseudomonas strains [1].

High impact information on m-Phenoxybenzoic acid

Pseudomonas pseudoalcaligenes POB310(pPOB) and Pseudomonas sp. strains B13-D5(pD30.9) and B13-ST1(pPOB) were introduced into soil microcosms containing 3-phenoxybenzoic acid (3-POB) in order to evaluate and compare bacterial survival, degradation of 3-POB, and transfer of plasmids to a recipient bacterium [1].
The results accord with the rapid association of the VLDL-(3PBA)DPG complexes with lipoprotein lipase of the capillary epithelium, followed by hydrolysis to 3PBA, metabolism and elimination but with a proportion being redistributed into adipose tissue, re-esterified and then eliminated relatively slowly [2].
The incorporation of 3-phenoxybenzoic acid and other xenobiotic acids into xenobiotic lipids by enzymes of the monoacylglycerol pathway in microsomes from adult and neonatal tissues [3].
Intestinal contents, homogenates, or microsomal fractions did not metabolize 3-phenoxybenzoic acid [4].
Metabolism of 3-phenoxybenzoic acid in isolated rat hepatocytes and renal tubule fragments [5].

Biological context of m-Phenoxybenzoic acid

The formation rate of 3-phenoxybenzoic acid followed saturation kinetics [6].
We tested three frequently encountered pyrethroids (fenvalerate, cypermethrin, permethrin) and their metabolite 3-phenoxybenzoic acid (3-PBA) for antiandrogenic and androgenic activity using a human androgen receptor (AR) mediated luciferase reporter gene assay in CV-1 African green monkey kidney cell [7].
The urine concentration of the metabolite varied from 2.4 to 51.7 micrograms/l. These results show that 3-phenoxybenzoic acid is suitable for biological monitoring for the assessment of exposure to deltamethrin [8].

Associations of m-Phenoxybenzoic acid with other chemical compounds

The direct hydrolysis products, cyclopropanic acid (Cl2CA), 3-phenoxybenzyl alcohol (PBalc), and 3-phenoxybenzoic acid (PBacid), were recovered at small percentages, ranging from 1 to 14% for Cl2CA and from 0.2 to 6% for PBalc and PBacid [9].
Permethrin, 3-phenoxybenzyl alcohol, 3-phenoxybenzaldehyde, and 3-phenoxybenzoic acid were analysed by HPLC [6].
The pyrethroid metabolites cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid, 3-phenoxybenzoic acid and fluorophenoxybenzoic acid were determined in the urine samples (limit of detection: 0.5 micrograms/l) by GC MS and the pyrethroids in plasma (limit of detection: 5 micrograms) GC-ECD [10].
In baker's yeast, the apparent Km of 3-phenoxybenzoic acid formation was several times larger than that for ethanol dehydrogenation [11].
Urine samples were collected for up to 5 days and analysed for the metabolites cis and trans 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (DCVA), 3-phenoxybenzoic acid (3PBA) and 3-(4'-hydroxyphenoxy) benzoic acid (4OH3PBA) following an acid hydrolysis procedure [12].

Gene context of m-Phenoxybenzoic acid

The formation of 3-phenoxybenzoic acid from 3-phenoxybenzyl alcohol was determined in (a) rabbit ears, single-pass perfused with a protein-free buffer, pH 7.4; (b) the microsomal fraction and its supernatant from homogenized rabbit skin; and (c) purified alcohol dehydrogenase from horse liver and baker's yeast [11].

References

Degradation of 3-phenoxybenzoic acid in soil by Pseudomonas pseudoalcaligenes POB310(pPOB) and two modified Pseudomonas strains. Halden, R.U., Tepp, S.M., Halden, B.G., Dwyer, D.F. Appl. Environ. Microbiol. (1999) [Pubmed]
The metabolism of the xenobiotic triacylglycerols, rac-1- and sn-2- (3-phenoxybenzoyl)-dipalmitoylglycerol, following intravenous administration to the rat. Haselden, J.N., Dodds, P.F., Hutson, D.H. Biochem. Pharmacol. (1998) [Pubmed]
The incorporation of 3-phenoxybenzoic acid and other xenobiotic acids into xenobiotic lipids by enzymes of the monoacylglycerol pathway in microsomes from adult and neonatal tissues. Moorhouse, K.G., Logan, C.J., Hutson, D.H., Dodds, P.F. Biochem. Pharmacol. (1990) [Pubmed]
Diphenyl ether cleavage of 3-phenoxybenzoic acid by chicken kidney microsomal preparations. Akhtar, M.H., Mahadevan, S. Drug Metab. Dispos. (1992) [Pubmed]
Metabolism of 3-phenoxybenzoic acid in isolated rat hepatocytes and renal tubule fragments. Huckle, K.R., Hutson, D.H., Millburn, P. Drug Metab. Dispos. (1984) [Pubmed]
Permethrin absorption not detected in single-pass perfused rabbit ear, and absorption with oxidation of 3-phenoxybenzyl alcohol. Bast, G.E., Taeschner, D., Kampffmeyer, H.G. Arch. Toxicol. (1997) [Pubmed]
Antiandrogenic activity of pyrethroid pesticides and their metabolite in reporter gene assay. Sun, H., Xu, X.L., Xu, L.C., Song, L., Hong, X., Chen, J.F., Cui, L.B., Wang, X.R. Chemosphere (2007) [Pubmed]
Biological monitoring of deltamethrin exposure in greenhouses. Tuomainen, A., Kangas, J., Liesivuori, J., Manninen, A. International archives of occupational and environmental health. (1996) [Pubmed]
Enantiomeric differences in permethrin degradation pathways in soil and sediment. Qin, S., Gan, J. J. Agric. Food Chem. (2006) [Pubmed]
Biological monitoring of pyrethroids in blood and pyrethroid metabolites in urine: applications and limitations. Leng, G., Kühn, K.H., Idel, H. Sci. Total Environ. (1997) [Pubmed]
Dehydrogenation of 3-phenoxybenzyl alcohol in isolated perfused rabbit skin, skin homogenate and purified dehydrogenases. Bast, G.E., Kampffmeyer, H.G. Skin Pharmacol. Appl. Skin Physiol. (1998) [Pubmed]
The metabolism of cypermethrin in man: differences in urinary metabolite profiles following oral and dermal administration. Woollen, B.H., Marsh, J.R., Laird, W.J., Lesser, J.E. Xenobiotica (1992) [Pubmed]

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