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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

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
Influence of culture conditions on the DNA-damaging effect of benzene and its metabolites in human peripheral blood mononuclear cells.
2001
Research of quality indices for cold-smoked salmon using a stepwise multiple regression of microbiological counts and physico-chemical parameters.
2001 Apr
Extensive deproteinization of Dictyostelium discoideum RNase P reveals a new catalytic activity.
2001 Apr
Bimetallic reactivity. Preparation and properties of bimetallic complexes formed by binucleating ligands bearing 4- and 6-coordinate sites.
2001 Apr 23
Protein dynamics control proton transfers to the substrate on the His72Asn mutant of p-hydroxybenzoate hydroxylase.
2001 Apr 3
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).
2001 Apr 9
Ab initio and density functional theory studies for the explanation of the antioxidant activity of certain phenolic acids.
2001 Feb
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
Treatment of a foul condensate from Kraft pulping with horseradish peroxidase and hydrogen peroxide.
2001 Feb
Minimizing postoperative drainage with 20% ferric chloride after chemical matricectomy with phenol.
2001 Feb
Biodegradation of phenol in a continuous process: comparative study of stirred tank and fluidized-bed bioreactors.
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
Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia.
2001 Jan
Reclassification of [Pseudomonas] doudoroffii (Baumann et al. 1983) into the genus Oceanomonas gen. nov. as Oceanomonas doudoroffii comb. nov., and description of a phenol-degrading bacterium from estuarine water as Oceanomonas baumannii sp. nov.
2001 Jan
Quantitative and qualitative effects of chemical peeling on photo-aged skin: an experimental study.
2001 Jan
Dendrimeric organochalcogen catalysts for the activation of hydrogen peroxide: improved catalytic activity through statistical effects and cooperativity in successive generations.
2001 Jan 10
An enzymic 'latch' on a global carbon store.
2001 Jan 11
Multifunctional antioxidant activity of HBED iron chelator.
2001 Jan 15
Studies on a single immunoglobulin-binding domain of protein L from Peptostreptococcus magnus: the role of tyrosine-53 in the reaction with human IgG.
2001 Jan 15
Recurrence of curetted and bone-grafted giant-cell tumours with and without adjuvant phenol therapy.
2001 Mar
Acting with awareness and care.
2001 Mar
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Determination of tartaric acid in wines by FIA with tubular tartrate-selective electrodes.
2001 Mar 1
Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water.
2001 Mar 16
Phenol derivatives accelerate inactivation kinetics in one inactivation-deficient mutant human skeletal muscle Na(+) channel.
2001 Mar 23
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
Fast determination of phenols in contaminated soils.
2001 Mar 9
NMR investigation of exchange dynamics and binding of phenol and phenolate in DODAC vesicular dispersions.
2012 Aug 2
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
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
ACTIVE MOIETY
Structure of Phenol
SALT/SOLVATE (PARENT)
Structure of POTASSIUM PHENOXIDE
SALT/SOLVATE (PARENT)
BUTYLPHENOL
SALT/SOLVATE (PARENT)
PROPYLPHENOL
SALT/SOLVATE (PARENT)
Structure of CALCIUM PHENOXIDE
SALT/SOLVATE (PARENT)
Structure of PHENOLATE SODIUM
NIH
NCATS
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