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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6O
Molecular Weight 94.1112
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Phenol

SMILES

OC1=CC=CC=C1

InChI

InChIKey=ISWSIDIOOBJBQZ-UHFFFAOYSA-N
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H

HIDE SMILES / InChI
Molecular Formula C6H6O
Molecular Weight 94.1112
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 https://www.drugbank.ca/drugs/DB03255

Phenol is an industrially important organic compound, produced on a large scale and used as a precursor to many materials and useful compounds. Phenol and its vapors are corrosive to the eyes, the skin, and the respiratory tract. The corrosive effect on skin and mucous membranes is due to a protein-degenerating effect. In medicine, phenol is used as an antiseptic and disinfectant. Phenol is also used as an oral analgesic or anesthetic in products such as Chloraseptic to treat sore throat pain, sore mouth, pain associated with canker sores and minor mouth irritation. Additionally, phenol and its related compounds are used in surgical ingrown toenail treatment, a process termed phenolization.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Oral ingestion or extensive application to skin can cause systemic toxicity, manifested primarily by CNS and cardiovascular effects; death may result.

Originator

Runge, F.F.
3
Sources: Phenol was discovered in 1834 by Friedlieb Ferdinand Runge, who extracted it (in impure form) from coal tar
Curator's Comment: http://babel.hathitrust.org/cgi/pt?id=wu.89048351654;view=1up;seq=81

Approval Year

1921
1467
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
PHENOL 1.4%

Approved Use

Temporarily relieves sore throat pain, sore mouth, pain associated with canker sores, minor mouth irritation.
Curative
Approved
8429
Unknown

Approved Use

Treatment of ingrown nails
PubMed

PubMed

TitleDatePubMed
Phenolization of bladder in treatment of massive intractable hematuria.
1975 Jan
Phenol as an adjuvant for local control in the treatment of giant cell tumour of the bone.
1999 Dec
Decomposition of hazardous organic materials in the solidification/stabilization process using catalytic-activated carbon.
2001
Influence of culture conditions on the DNA-damaging effect of benzene and its metabolites in human peripheral blood mononuclear cells.
2001
Extensive deproteinization of Dictyostelium discoideum RNase P reveals a new catalytic activity.
2001 Apr
Stability analysis of the biodegradation of mixed wastes in a continuous bioreactor with cell recycle.
2001 Apr
Ketene reactions with the aminoxyl radical tempo: preparative, kinetic, and theoretical studies.
2001 Apr 20
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).
2001 Apr 9
Structural determinants for AMPA agonist activity of aryl or heteroaryl substituted AMPA analogues. Synthesis and pharmacology.
2001 Feb
Phenolic ablation of the nail matrix.
2001 Feb
[Pharmacological and clinical properties of beraprost sodium, orally active prostacyclin analogue].
2001 Feb
Treatment of a foul condensate from Kraft pulping with horseradish peroxidase and hydrogen peroxide.
2001 Feb
Optimised sample DNA preparation for detection of Chlamydia trachomatis in synovial tissue by polymerase chain reaction and ligase chain reaction.
2001 Feb
Kinetics and mechanism of the oxidation of a substituted phenol by a superoxochromium(III) ion.
2001 Feb 12
Experimental and computational mapping of the binding surface of a crystalline protein.
2001 Jan
A new surgical therapeutic approach to pincer nail deformity.
2001 Jan
Quantitative and qualitative effects of chemical peeling on photo-aged skin: an experimental study.
2001 Jan
Studies of the chemical selectivity of hapten, reactivity, and skin sensitization potency. 1. Synthesis and studies on the reactivity toward model nucleophiles of the (13)C-labeled skin sensitizers hex-1-ene- and hexane-1,3-sultones.
2001 Jan
Lipid A and O-chain modifications cause Rhizobium lipopolysaccharides to become hydrophobic during bacteroid development.
2001 Jan
Determination of mycophenolic acid and mycophenolate mofetil by high-performance liquid chromatography using postcolumn derivatization.
2001 Jan 1
An enzymic 'latch' on a global carbon store.
2001 Jan 11
Determination of phenols in soil by supercritical fluid extraction-capillary electrochromatography.
2001 Jan 12
Quantification of derivatives of bisphenol A diglycidyl ether (BADGE) and novolac glycidyl ether (NOGE) migrated from can coatings into tuna by HPLC/fluorescence and MS detection.
2001 Jan 2
[Features of extracting phenol and 4-methylphenol from aqueous solutions].
2001 Jan-Feb
QSAR models using a large diverse set of estrogens.
2001 Jan-Feb
Airway responses to a diluent used in the methacholine challenge test.
2001 Mar
Isolation of genomic DNA from feathers.
2001 Mar
Protection against nitrofurantoin-induced oxidative stress by coelenterazine analogues and their oxidation products in rat hepatocytes.
2001 Mar
Optimization of random amplification of polymorphic DNA analysis for molecular subtyping of Escherichia coli O157.
2001 Mar
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Different generation of inhibitors against gallic acid-induced apoptosis produces different sensitivity to gallic acid.
2001 Mar
Relationship between effects of phenolic compounds on the generation of free radicals from lactoperoxidase-catalyzed oxidation of NAD(P)H or GSH and their DPPH scavenging ability.
2001 Mar
Antioxidant activity of resveratrol compared with common food additives.
2001 Mar
Microionization constants: novel approach for the determination of the zwitterionic equilibrium of hydroxyphenylalkylamines by photometric titration.
2001 Mar 14
Density functional study of tetraphenolate and calix[4]arene complexes of early transition metals.
2001 Mar 26
On-line flow sample stacking in a flow injection analysis-capillary electrophoresis system: 2000-fold enhancement of detection sensitivity for priority phenol pollutants.
2001 Mar 30
The effects of phenolic components of tea on the production of pro- and anti-inflammatory cytokines by human leukocytes in vitro.
2001 Mar 7
A new phenoxyacetate-based linker system for the solid-phase synthesis of oligosaccharides.
2001 Mar 8
Fast determination of phenols in contaminated soils.
2001 Mar 9
Photo-Fries rearrangements of phenyl phenylacylates in polyethylene films: comparison of reactivity and selectivity with 1-naphthyl phenylacylates.
2001 Mar 9
Reaction of human myoglobin and H2O2. Electron transfer between tyrosine 103 phenoxyl radical and cysteine 110 yields a protein-thiyl radical.
2001 May 11
Patents

Patents

US3159635
3
US3304225
3

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: The interaction between phenol molecules, both in their undissociated and dissociated states, and cationic dioctadecyl dimethylammonium chloride (DODAC) vesicles were thoroughly investigated using NMR techniques. In particular, diffusion and relaxation measurements, combined with the two sites Kärger model, were used to evaluate the exchange dynamics and the binding of the aromatic molecules to the vesicles. The results reveal that, besides concentration and vesicle preparation method, pH conditions have the biggest impact on the phenol sorption behavior. Although the dissociated form of phenol formed at high pH is more hydrophilic, the results indicated that phenol-DODAC interactions were largely favored in basic conditions as a consequence of the strong electrostatic interaction between the phenolate anions and the cationic surfactant headgroup.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:37 GMT 2023
Edited
by admin
on Fri Dec 15 14:58:37 GMT 2023
Record UNII
339NCG44TV
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
Phenol
EP   FHFI   HSDB   II   INCI   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
PHENOL [USP-RS]
Common Name English
PHENOL [INCI]
Common Name English
SALICYLIC ACID IMPURITY C [EP IMPURITY]
Common Name English
BENZENE, HYDROXY-
Systematic Name English
Phenol [WHO-DD]
Common Name English
PHENIC ACID
Common Name English
PHENOL [II]
Common Name English
SALICYLIC ACID RELATED COMPOUND C [USP IMPURITY]
Common Name English
HEXYLRESORCINOL IMPURITY A [EP IMPURITY]
Common Name English
METHYL SALICYLATE IMPURITY B [EP]
Common Name English
2-ALLPHENOL
Common Name English
PHENOL [EP MONOGRAPH]
Common Name English
ENT-1814
Code English
CARBOLICUM ACIDUM [HPUS]
Common Name English
PHENOL [FHFI]
Common Name English
PHENYL ALCOHOL
Systematic Name English
CARBOLICUM ACIDUM
HPUS  
Common Name English
LIQUEFIED PHENOL
Common Name English
LIQUIFIED PHENOL
Common Name English
PHENOL [MART.]
Common Name English
PHENOL [HSDB]
Common Name English
PHENOL [USP MONOGRAPH]
Common Name English
PHENOL [MI]
Common Name English
MONOHYDROXYBENZENE
Systematic Name English
PHENOL [JAN]
Common Name English
NSC-36808
Code English
PHENOL, LIQUIFIED
Common Name English
PHENOL,LIQUIFIED [VANDF]
Common Name English
CARBOLIC ACID
Common Name English
PHENYLIC ALCOHOL
Common Name English
PHENOL [IARC]
Common Name English
PHENYL HYDROXIDE
Systematic Name English
PHENOL [VANDF]
Common Name English
METACRESOL IMPURITY A [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QC05BB05
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
DSLD 1842 (Number of products:5)
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
WHO-VATC QD08AE99
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
WHO-ATC D08AE03
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
EPA PESTICIDE CODE 64001
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
WHO-ATC N01BX03
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
WHO-VATC QN01BX03
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
NCI_THESAURUS C45494
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
WHO-ATC C05BB05
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
CFR 21 CFR 310.531
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
JECFA EVALUATION PHENOL
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
WHO-ATC R02AA19
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
WHO-VATC QD08AE03
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
WHO-VATC QR02AA19
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
Code System Code Type Description
SMS_ID
100000091344
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
MESH
D019800
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
DAILYMED
339NCG44TV
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
NCI_THESAURUS
C1191
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
PUBCHEM
996
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL14060
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
RXCUI
33290
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
CAS
108-95-2
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
DRUG CENTRAL
4266
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
RXCUI
239351
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
ALTERNATIVE
WIKIPEDIA
PHENOL
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
MERCK INDEX
m8624
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY Merck Index
JECFA MONOGRAPH
570
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-632-7
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
EVMPD
SUB12552MIG
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
NSC
36808
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
RS_ITEM_NUM
1524806
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
DRUG BANK
DB03255
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
CHEBI
15882
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
FDA UNII
339NCG44TV
Created by admin on Fri Dec 15 14:58:38 GMT 2023 , Edited by admin on Fri Dec 15 14:58:38 GMT 2023
PRIMARY
Related Record Type Details
Structure of POTASSIUM PHENOXIDE
SALT/SOLVATE -> PARENT
GLYCYRRHIZA GLABRA
PARENT -> CONSTITUENT ALWAYS PRESENT
BUTYLPHENOL
SALT/SOLVATE -> PARENT
PROPYLPHENOL
SALT/SOLVATE -> PARENT
PHENOL, LIQUEFIED
SUB_CONCEPT->SUBSTANCE
WOOD CREOSOTE
PARENT -> CONSTITUENT ALWAYS PRESENT
BEECHWOOD CREOSATE
Structure of CALCIUM PHENOXIDE
SALT/SOLVATE -> PARENT
Structure of PHENOLATE SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of HEXYLRESORCINOL
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Methyl salicylate
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP
Structure of CHLOROQUINE PHOSPHATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of Salicylic acid
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of Salicylic acid
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Structure of MAGNESIUM SALICYLATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of METACRESOL
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP
Related Record Type Details
Structure of Phenol
ACTIVE MOIETY
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