P-CHLOROBENZOIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H5ClO2
Molecular Weight	156.566
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=C(Cl)C=C1

InChI

InChIKey=XRHGYUZYPHTUJZ-UHFFFAOYSA-N

InChI=1S/C7H5ClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)

HIDE SMILES / InChI

Molecular Formula	C7H5ClO2
Molecular Weight	156.566
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6107234 | https://www.ncbi.nlm.nih.gov/pubmed/1154801 | https://www.ncbi.nlm.nih.gov/pubmed/3768082 | https://www.ncbi.nlm.nih.gov/pubmed/3117062 | http://www.drugfuture.com/chemdata/p-Chlorobenzoic-Acid.html

p-Chlorobenzoic acid is a major metabolite of analgesic agent zomepirac sodium in rat (present as conjugates) and mouse and a minor one in monkey and man. It is a metabolite of antidepressant Lofepramine hydrochloride, and anxiolytic and a muscle relaxant Chlormezanone too. Sodium salt of p-Chlorobenzoic acid is used as a preservative. p-Chlorobenzoic acid may prove useful clinically to prevent and reverse the accumulation of toxic levels of acyl- and arylCoA esters. If the hepatic damage in Reye’s Syndrome is due to the dead-end formation of the CoA esters of acyl- and aryl-CoA esters, then p-chlorobenzoic acid may block their formation, thereby relieving the inhibitions of gluconeogenesis and urea synthesis and preventing some of the damage to the liver.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
CoA esters of acyl- and aryl-CoA esters formation 2 Target ID: CoA esters of acyl- and aryl-CoA esters formation Sources: https://www.ncbi.nlm.nih.gov/pubmed/3117062	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Reye syndrome 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3117062	Preventing		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Degradation of chlorinated biphenyls and products of their bioconversion by Rhodococcus sp. B7a strain].	2011-01-26	21261074
Synthesis and antiviral activity of 5‑(4‑chlorophenyl)-1,3,4-thiadiazole sulfonamides.	2010-12-09	21150824
Photoreactivity of carboxylated single-walled carbon nanotubes in sunlight: reactive oxygen species production in water.	2010-09-01	20687543
Evolution of absorbance spectra of ozonated wastewater and its relationship with the degradation of trace-level organic species.	2010-08-15	20704209
Removal of 4-chlorobenzoic acid from spiked hydroponic solution by willow trees (Salix viminalis).	2010-08	20336492
Application of preparative capillary gas chromatography (pcGC), automated structure generation and mutagenicity prediction to improve effect-directed analysis of genotoxicants in a contaminated groundwater.	2010-05	20119663
Wheel-like Mn(II)6 and Ni(II)6 complexes from the use of 2-pyridinealdoxime and carboxylates.	2010-04-21	20354610
Induction of functional cytochrome P450 and its involvement in degradation of benzoic acid by Phanerochaete chrysosporium.	2010-04	19787435
Dissecting the role of critical residues and substrate preference of a Fatty Acyl-CoA Synthetase (FadD13) of Mycobacterium tuberculosis.	2009-12-21	20027301
Synthesis and antimicrobial activity of 3-(1,3,4-Oxadiazol-2-yl)quinazolin-4(3H)-ones.	2009-12-17	21179342
Kinetics and oxidative mechanism for H2O2-enhanced iron-mediated aeration (IMA) treatment of recalcitrant organic compounds in mature landfill leachate.	2009-09-30	19467776
Application of monolithic columns in pharmaceutical analysis. Determination of indomethacin and its degradation products.	2009-08	19603393
Ozonation of metoprolol: elucidation of oxidation pathways and major oxidation products.	2009-07-15	19708384
Toxicity and quantitative structure-activity relationships of benzoic acids to Pseudokirchneriella subcapitata.	2009-06-15	18990494
Analysis of proteins with the 'hot dog' fold: prediction of function and identification of catalytic residues of hypothetical proteins.	2009-05-28	19473548
The mechanism of domain alternation in the acyl-adenylate forming ligase superfamily member 4-chlorobenzoate: coenzyme A ligase.	2009-05-19	19320426
Catalytic ozonation of p-chlorobenzoic acid by activated carbon and nickel supported activated carbon prepared from petroleum coke.	2009-04-15	18667273
Degradation of selected pharmaceuticals in aqueous solution with UV and UV/H(2)O(2).	2009-04	19232423
The effect of electrode material on the generation of oxidants and microbial inactivation in the electrochemical disinfection processes.	2009-03	19084255
Synthesis of alpha-amyrin derivatives and their in vivo antihyperglycemic activity.	2009-03	18947904
Ozonation and advanced oxidation by the peroxone process of ciprofloxacin in water.	2009-01-30	18513860
Degradation of pCBA by catalytic ozonation in natural water.	2009	19342818
Oxidation of p-chlorotoluene and cyclohexene catalysed by polymer-anchored oxovanadium(IV) and copper(II) complexes of amino acid derived tridentate ligands.	2008-08-28	18682861
Mechanism of 4-chlorobenzoate:coenzyme a ligase catalysis.	2008-08-05	18620421
Structural characterization of a 140 degrees domain movement in the two-step reaction catalyzed by 4-chlorobenzoate:CoA ligase.	2008-08-05	18620418
Identification of genes coding for hydrolytic dehalogenation in the metagenome derived from a denitrifying 4-chlorobenzoate degrading consortium.	2008-04	18355280
Epimers of bicyclo[2.2.2]octan-2-ol derivatives with antiprotozoal activity.	2008-04	17698258
(4-Chloro-benzoato)bis(5-methyl-2-pyridylamine)silver(I).	2008-03-29	21202038
Variability of enzyme system of Nocardioform bacteria as a basis of their metabolic activity.	2008-03-28	18368545
trans-Diaqua-bis(ethyl-enediamine-κN,N')copper(II) bis[3-(3-pyrid-yl)propionate] dihydrate.	2008-03-05	21201981
FT-IR, FT-Raman spectra and ab initio HF, DFT vibrational analysis of p-chlorobenzoic acid.	2008-03	17658292
Diaqua-bis(4-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).	2008-02-29	21201885
2-(4-Chloro-benzo-yl)-3,6-dimethoxy-naphthalene.	2008-02-22	21201947
Structure and denaturation of 4-chlorobenzoyl coenzyme A dehalogenase from Arthrobacter sp. strain TM-1.	2008-02	17431803
Benzoyl-methyl 4-chloro-benzoate.	2008-01-23	21201527
Rational redesign of the 4-chlorobenzoate binding site of 4-chlorobenzoate: coenzyme a ligase for expanded substrate range.	2007-12-18	18027984
2-(1H-Benzotriazol-1-yl)-1-(4-bromo-benzo-yl)ethyl 4-methyl-benzoate.	2007-12-06	21200686
Analysis of p-chlorobenzoic acid in water by liquid chromatography-tandem mass spectrometry.	2007-09-14	17689544
Preparation of biotic and abiotic iron oxide nanoparticles (IOnPs) and their properties and applications in heterogeneous catalytic oxidation.	2007-07-01	17695923
Expeditious and convenient synthesis of pregnanes and its glycosides as potential anti-dyslipidemic and anti-oxidant agents.	2007-07-01	17485213
Cloning of the Arthrobacter sp. FG1 dehalogenase genes and construction of hybrid pathways in Pseudomonas putida strains.	2007-07	17384944
2,2-Dimethyl-5-nitroso-1,3-dioxan-5-yl benzoate, 2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl 4-chlorobenzoate and 5-nitroso-1,3-dioxan-5-yl 4-chlorobenzoate.	2007-06	17551206
Organic micropollutants degradation in ozone-loaded system with perfluorinated solvent.	2007-06	17459452
Degradation of octylphenol and nonylphenol by ozone - part II: indirect reaction.	2007-06	17349672
The ROH,UV concept to characterize and the model uv/H202 process in natural waters.	2007-04-01	17438814
Temperature-dependent biotransformation of 2,4'-dichlorobiphenyl by psychrotolerant Hydrogenophaga strain IA3-A: higher temperatures prevent excess accumulation of problematic meta-cleavage products.	2007-04	17397486
Isolation and preliminary characterization of a 3-chlorobenzoate degrading bacteria.	2007	17918596
Advantages of application of UPLC in pharmaceutical analysis.	2006-01-15	18970409
Nitrite reductase genes in halobenzoate degrading denitrifying bacteria.	2003-04-01	19719666
The use of mutants to discern the degradation pathway of 3,4'-dichlorobiphenyl in Pseudomonas acidovorans M3GY.	2002-10-01	19709267

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

p-Chlorobenzoic acids (1 mM) prevented the inhibition of glucose synthesis in hepatocytes incubated with p-octylbenzoic acid, paminobenzoic acid, or valproic acid.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:42:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:42:31 GMT 2025`
Record UNII	IC7888DF4L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

P-CHLOROBENZOIC ACID

Common Name

English

NSC-32738

Preferred Name

English

P-chlorobenzoic acid [WHO-DD]

Common Name

English

P-CHLOROBENZOIC ACID [HSDB]

Common Name

English

INDOMETHACIN RELATED COMPOUND B [USP-RS]

Common Name

English

BENZOIC ACID, P-CHLORO-

Common Name

English

CHLOROBENZOIC ACID, P-

Common Name

English

INDOMETACIN IMPURITY A [EP IMPURITY]

Common Name

English

ACEMETACIN IMPURITY A [EP IMPURITY]

Common Name

English

CHLORODRACYLIC ACID

Common Name

English

BENZOIC ACID, 4-CHLORO-

Systematic Name

English

4-CHLOROBENZOIC ACID

Systematic Name

English

P-CHLOROBENZOIC ACID [MI]

Common Name

English

Code System Code Type Description

CHEBI

30747