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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

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

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHENOL 1.4%

Approved Use

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

Approved Use

Treatment of ingrown nails
PubMed

PubMed

TitleDatePubMed
Carboxylation of phenylphosphate by phenol carboxylase, an enzyme system of anaerobic phenol metabolism.
1992 Jun
Expression of LRP and MDR1 in locally advanced breast cancer predicts axillary node invasion at the time of rescue mastectomy after induction chemotherapy.
2001
Polymorphisms in the Mn-SOD and EC-SOD genes and their relationship to diabetic neuropathy in type 1 diabetes mellitus.
2001
Fungal virulence studies come of age.
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
Ketene reactions with the aminoxyl radical tempo: preparative, kinetic, and theoretical studies.
2001 Apr 20
Ab initio and density functional theory studies for the explanation of the antioxidant activity of certain phenolic acids.
2001 Feb
Comparative contents of dietary fiber, total phenolics, and minerals in persimmons and apples.
2001 Feb
Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups.
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
Heavy metal removal with Mexican clinoptilolite: multi-component ionic exchange.
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
Urinary benzene as a biomarker of exposure among occupationally exposed and unexposed subjects.
2001 Feb
Kinetics and mechanism of the oxidation of a substituted phenol by a superoxochromium(III) ion.
2001 Feb 12
Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation.
2001 Feb 15
Neural mechanisms involved in the delay of gastric emptying and gastrointestinal transit of liquid after thoracic spinal cord transection in awake rats.
2001 Feb 20
Temperature dependence of DCDD/F isomer distributions from chlorophenol precursors.
2001 Feb-Mar
An experimental and numerical study of the thermal oxidation of chlorobenzene.
2001 Feb-Mar
Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia.
2001 Jan
Spasticity management: an overview.
2001 Jan
Near infrared spectra (4000-10 500 cm-1) of phenol-OH and phenol-OD in carbon tetrachloride.
2001 Jan
Electrooxidation of phenol by catalase immobilized on graphite electrodes.
2001 Jan
Exposure to chemical agents in Swedish aluminum foundries and aluminum remelting plants--a comprehensive survey.
2001 Jan
Triarylpyrazoles with basic side chains: development of pyrazole-based estrogen receptor antagonists.
2001 Jan
Determination of mycophenolic acid and mycophenolate mofetil by high-performance liquid chromatography using postcolumn derivatization.
2001 Jan 1
Preparations, characterizations, and structures of (biimidazole)dihalobis(triphenylphosphine)rhenium(III) salts: strong ion-pairing and acid-base properties.
2001 Jan 1
An enzymic 'latch' on a global carbon store.
2001 Jan 11
Quinoprotein glucose dehydrogenase modified thick-film electrodes for the amperometric detection of phenolic compounds in flow injection analysis.
2001 Jan 2
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
Self-assembly and selective guest binding of three-dimensional open-framework solids from a macrocyclic complex as a trifunctional metal building block.
2001 Jan 5
[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
Corneal sensitivity and some properties of the tear film after laser in situ keratomileusis.
2001 Jan-Feb
Comparative QSAR: on the toxicology of the phenolic OH moiety.
2001 Mar
Recurrence of curetted and bone-grafted giant-cell tumours with and without adjuvant phenol therapy.
2001 Mar
Isolation of genomic DNA from feathers.
2001 Mar
Pincer nails: definition and surgical treatment.
2001 Mar
Optimization of random amplification of polymorphic DNA analysis for molecular subtyping of Escherichia coli O157.
2001 Mar
Enhanced biodegradation of petrochemical wastewater using ozonation and BAC advanced treatment system.
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
Binding of substituted phenol and aniline derivatives to the corn protein zein studied by high-performance liquid chromatography.
2001 Mar 25
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
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
NMR investigation of exchange dynamics and binding of phenol and phenolate in DODAC vesicular dispersions.
2012 Aug 2
Patents

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 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:37 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
DSLD 1842 (Number of products:5)
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
WHO-VATC QD08AE99
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
WHO-ATC D08AE03
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
EPA PESTICIDE CODE 64001
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
WHO-ATC N01BX03
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
WHO-VATC QN01BX03
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
NCI_THESAURUS C45494
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
WHO-ATC C05BB05
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
CFR 21 CFR 310.531
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
JECFA EVALUATION PHENOL
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
WHO-ATC R02AA19
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
WHO-VATC QD08AE03
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
WHO-VATC QR02AA19
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
Code System Code Type Description
SMS_ID
100000091344
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
MESH
D019800
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
DAILYMED
339NCG44TV
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
NCI_THESAURUS
C1191
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
PUBCHEM
996
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL14060
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
RXCUI
33290
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
CAS
108-95-2
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
DRUG CENTRAL
4266
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
RXCUI
239351
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
ALTERNATIVE
WIKIPEDIA
PHENOL
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
MERCK INDEX
m8624
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY Merck Index
JECFA MONOGRAPH
570
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-632-7
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
EVMPD
SUB12552MIG
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
NSC
36808
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
RS_ITEM_NUM
1524806
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
DRUG BANK
DB03255
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
CHEBI
15882
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
FDA UNII
339NCG44TV
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SUB_CONCEPT->SUBSTANCE
PARENT -> CONSTITUENT ALWAYS PRESENT
BEECHWOOD CREOSATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP
Related Record Type Details
ACTIVE MOIETY