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Details

Stereochemistry ACHIRAL
Molecular Formula C6H5ClO
Molecular Weight 128.556
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-Chlorophenol

SMILES

OC1=CC=C(Cl)C=C1

InChI

InChIKey=WXNZTHHGJRFXKQ-UHFFFAOYSA-N
InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H

HIDE SMILES / InChI
Molecular Formula C6H5ClO
Molecular Weight 128.556
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://drugs-about.com/drugs-e/endotine.html and http://www.ncbi.nlm.nih.gov/pubmed/1337555

Parachlorophenol is a disinfectant effective against most gram-negative organisms, it is currently used in endodontic therapy in a 35 per cent concentration as camphorated parachlorophenol for the disinfection of root canals. It is marketed under the brand name Endotine in France.

Originator

Walkoff, O.
2
Curator's Comment: Was introduced into dentistry as root canal antiseptic by Walkoff in 1891

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Enterococcus faecalis growth
2
Target ID: Enterococcus faecalis growth
Inhibitor
8504
Porphyromonus gingivalis growth
2
Target ID: Porphyromonus gingivalis growth
Inhibitor
8504
Fusobacterium nucleatum growth
2
Target ID: Fusobacterium nucleatum growth
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
511
Unknown

Approved Use

Unknown
Curative
Approved
8583
Endotine

Approved Use

Root canal antiseptic
PubMed

PubMed

TitleDatePubMed
Hard coal as a potential low-cost adsorbent for removal of 4-chlorophenol from water.
2016
Simulation of bioremediation of chlorophenols in a sandy aquifer.
2003-01
Effects of parachlorophenol and camphorated parachlorophenol on the phagocytic activities of a murine macrophage cell line (RAW264.7).
2002-12
Separation and determination of phenolic compounds by capillary electrophoresis with chemiluminescence detection.
2002-11-29
Identification of 2,4-dichlorophenol in females of the American dog tick, Dermacentor variabilis (Acari: Ixodidae), and its possible role as a component of the attractant sex pheromone.
2002-11
The role of hydrogen bonding on the h-atom-donating abilities of catechols and naphthalene diols and on a previously overlooked aspect of their infrared spectra.
2002-10-30
Development of supercritical fluid extraction with a solid-phase trapping for fast estimation of toxic load of polychlorinated dibenzo-p-dioxins-dibenzofurans in sawmill soil.
2002-10-25
Concentration of chlorophenols in water with sodium dodecylsulfate-gamma-alumina admicelles for high-performance liquid chromatographic analysis.
2002-10-04
Thermodynamic study of adsorption of phenolic compounds onto Amberlite XAD-4 polymeric adsorbents and its acetylized derivative MX-4.
2002-10
Cis/trans isomerisation of unsaturated fatty acids in a cardiolipin synthase knock-out mutant of Pseudomonas putida P8.
2002-10
Retroviral vectors for establishing tetracycline-regulated gene expression in an otherwise recalcitrant cell line.
2002-09-03
Detoxification of phenolic solutions with horseradish peroxidase and hydrogen peroxide.
2002-09
Expression of beta-galactosidase by recombinant respiratory syncytial viruses for microneutralization assay.
2002-09
Degradation of 4-chlorophenol by the white rot fungus Phanerochaete chrysosporium in free and immobilized cultures.
2002-09
COX-2 selective inhibition reverses the trophic properties of gastrin in colorectal cancer.
2002-08-27
Increased activity of in situ catalysts for alkyne metathesis.
2002-08-22
Evaluation of interactive toxicity of chlorophenols in water and soil using lux-marked biosensors.
2002-08
Photochemical behaviour of dichlorprop [(+/-)-2-(2,4-dichlorophenoxy)propanoic acid] in aqueous solution.
2002-08
Lethal body residue of chlorophenols and mixtures of chlorophenols in benthic organisms.
2002-08
Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.
2002-07-15
Reversed flow injection spectrophotometric determination of low residuals of chlorine dioxide in water using chlorophenol red.
2002-07
Electrochemical removal of p-nonylphenol from dilute solutions using a carbon fiber anode.
2002-07
Effects of 2,4-dichlorophenol on activated sludge.
2002-07
Spatial distibution and temporal accumulation of polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls in the Gulf of Finland.
2002-06-15
Impact of protein binding on the availability and cytotoxic potency of organochlorine pesticides and chlorophenols in vitro.
2002-06-14
Porous polysilsesquioxanes for the adsorption of phenols.
2002-06-01
Acute toxicity of crude and dispersed oil to Octopus pallidus (Hoyle, 1885) hatchlings.
2002-06
Adsorption of phenolic compounds from aqueous solutions by a water-compatible hypercrosslinked polymeric adsorbent.
2002-06
Kinetic modeling of fenton oxidation of phenol and monochlorophenols.
2002-06
Acute lethal toxicity of environmental pollutants to aquatic organisms.
2002-06
Substrate-dependent autoaggregation of Pseudomonas putida CP1 during the degradation of mono-chlorophenols and phenol.
2002-06
Solar photocatalysis: a clean process for water detoxification.
2002-05-27
Dimethyl sulfoxide blocks herpes simplex virus-1 productive infection in vitro acting at different stages with positive cooperativity. Application of micro-array analysis.
2002-05-24
Case-control study evaluating the homogeneity and heterogeneity of risk factors between sinonasal and nasopharyngeal cancers.
2002-05-01
A portable toxicity biosensor using freeze-dried recombinant bioluminescent bacteria.
2002-05
Detection of insulin-regulated GLUT4-translocation by the insertion of a protein C epitope in L6 myoblasts.
2002-04-18
Adsorption of p-chlorophenol from aqueous solutions on bentonite and perlite.
2002-03-29
Photocatalytic degradation of aqueous 4-chlorophenol by silica-immobilized polyoxometalates.
2002-03-15
[Degradation of 4-chlorophenol in aqueous solution by high-voltage pulsed discharge-ozone technology].
2002-03
Radical/radical vs radical/molecule reactions in the formation of PCDD/Fs from (chloro)phenols in incinerators.
2002-03
Kinetic studies on UV-photodegradation of some chlorophenols using TiO2 catalyst.
2002-03
Electrochemical oxidation of chlorophenols at a boron-doped diamond electrode and their determination by high-performance liquid chromatography with amperometric detection.
2002-02-15
Kinetics of phenol and chlorophenol utilization by Acinetobacter species.
2002-02
Adsorption of phenol and m-chlorophenol on organobentonites and repeated thermal regeneration.
2002
[Prophylactic efficiency of tietasol and oxymethyluracyl against chlorphenols exposure in experimental and real conditions].
2002
4-chlorophenol degradation by chloroperoxidase from Caldariomyces fumago: formation of insoluble products.
2002
Adsorption of phenols by papermill sludges.
2002
Sonochemical degradation of aromatic organic pollutants.
2002
Degradation of 2,3,4,6-tetrachlorophenol at low temperature and low dioxygen concentrations by phylogenetically different groundwater and bioreactor bacteria.
2001
Urinary excretion of chlorinated phenols in saw-mill workers.
1991
Patents

Patents

03947394
2
04094900
2
04242493
2
04621095
3
04751312
2
JP1022925A
2
JP2000171398A
2
JP2002508316A
4
JP2007518867A
6
JP3587859B2
4
JPH00598575A
2
JPH00864640A
2
JPH01221423A
2
JPH01259032A
2
JPH0220524A
2
JPH0283450A
2
JPH03259097A
2
JPH04149259A
2
JPH04288303A
2
JPH05186590A
2
JPH0598575A
2
JPH08127570A
2
JPH1112929A
2
JPS54134797A
2
JPS5610521A
2
JPS56139415A
2
JPS5635998A
2
JPS5653631A
2
JPS57163497A
4
JPS58187430A
2
JPS58225174A
2
JPS61162523A
2
JPS61207351A
2
JPS62223144A
8
JPS62290752A
2
JPS6341434A
2
JPS638388A
2
JPS6443523A
2
JPS6457613A
2
WO2015173277A1
2

Sample Use Guides

In Vivo Use Guide
Male mice were administered 4-Chlorophenol, 1.5 mmol/kg body weight, i.p.
Route of Administration: Intraperitoneal
In Vitro Use Guide
In fibroblast L929 cells the effective concentration for half-maximal response (EC50 value at 24 h for 4-Chlorophenol is 2.18 mmol/L and the EC50 value at 48 h is 1.18 mmol/L by using 3-(4,5-dimethylthiazd-2-yl)-2,5-diphenyltentrazolium bromide (MTT) reduction assay.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:33:04 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:04 GMT 2025
Record UNII
3DLC36A01X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
p-Chlorophenol
INCI   MI  
INCI  
Preferred Name English
4-Chlorophenol
Systematic Name English
PARACHLOROPHENOL [USP-RS]
Common Name English
PARACHLOROPHENOL [VANDF]
Common Name English
4-Chlorphenol [WHO-DD]
Common Name English
PARACHLOROPHENOL [MART.]
Common Name English
Parachlorophenol
HSDB   JAN   MART.   USP   USP-RS   VANDF  
Systematic Name English
PARACHLOROPHENOL [USP MONOGRAPH]
Common Name English
PARACHLOROPHENOL [HSDB]
Common Name English
P-CHLOROPHENOL [MI]
Common Name English
PARACHLOROPHENOL [JAN]
Common Name English
NSC-2877
Code English
4-CHLORPHENOL
WHO-DD  
Common Name English
PHENOL, 4-CHLORO-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C87268
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
DRUG BANK
DB13154
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
RS_ITEM_NUM
1496802
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-402-6
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
ChEMBL
CHEMBL57053
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
MESH
C029107
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
NSC
2877
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
RXCUI
14982
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID1021871
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PRIMARY
CAS
106-48-9
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
MERCK INDEX
m3427
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY Merck Index
HSDB
1414
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
CHEBI
28078
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
WIKIPEDIA
4-Chlorophenol
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
FDA UNII
3DLC36A01X
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
EVMPD
SUB55726
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
PUBCHEM
4684
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
SMS_ID
100000133835
Created by admin on Mon Mar 31 17:33:04 GMT 2025 , Edited by admin on Mon Mar 31 17:33:04 GMT 2025
PRIMARY
NIH
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