U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C7H8O
Molecular Weight 108.1378
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METACRESOL

SMILES

CC1=CC(O)=CC=C1

InChI

InChIKey=RLSSMJSEOOYNOY-UHFFFAOYSA-N
InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3

HIDE SMILES / InChI
Metacresol (m-cresol or 3-methylphenol) is colorless, yellowish liquid. It is used as a bactericide for control of crown gall and olive knot on certain fruit and nut trees and ornamentals and the genetic/physiological disorder burr knot on apples. Currently, one product is registered which contains both m-cresol and xylenol. Used as disinfectant/bacteriocide/germicide for animal pathogenic bacteria (G- and G+ vegetative) in households, sickrooms, hospitals, veterinary clinics, and veterinary hospitals; on surgical instruments, diagnostic instruments/equipment and on hospital critical rubber/plastic items. Used as an insecticide and miticide on dogs for treatment of lice and fleas. It is also used for making synthetic resins; in photographic developers, explosives. Additionally, m-cresol is chemical intermediate for thymol used in cough/cold medicinals, synthetic pyrethroid insecticides, 3-methyl-6-t-butylphenol, trinitro-m-cresol for explosives, and phenolic resins; disinfectant ingredient; ore flotation agent; solvent. m-Cresol, either pure or mixed with p-cresol, is important in the production of contact herbicides. m-Cresol is also a precursor to the pyrethroid insecticides. Furthermore, many flavor and fragrance compounds, such as (-)-methanol and musk ambrette, are derived from m-cresol. Several important antioxidants including synthetic vitamin E are produced from m-cresol. m-cresol is used as a topical dental antiseptic. m-cresol is an effective antimicrobial preservative and is used at low levels (0.3%) in multi-dose peptide and protein formulations. m-cresol has been shown to cause protein aggregation.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Determination of urinary ortho- and meta-cresol in humans by headspace SPME gas chromatography/mass spectrometry.
2005-03-25
Inhibition of cyclooxygenase activity, platelet aggregation and thromboxane B2 production by two environmental toxicants: m- and o-cresol.
2005-03-01
Determination of phenolic compounds by a polyphenol oxidase amperometric biosensor and artificial neural network analysis.
2005-02-15
Construction of a radiation hybrid map of chicken chromosome 2 and alignment to the chicken draft sequence.
2005-02-04
Effect of toluene and cresols on Na+,K+-ATPase, and serotonin in rat brain.
2005-02
Controlling the regiospecific oxidation of aromatics via active site engineering of toluene para-monooxygenase of Ralstonia pickettii PKO1.
2005-01-07
Ability of fourteen chemical agents used in dental practice to induce chromosome aberrations in Syrian hamster embryo cells.
2005-01
Quantifying individual fruit fly consumption with Anastrepha suspensa (Diptera: Tephritidae).
2004-12
Bioremediation of crystal violet using air bubble bioreactor packed with Pseudomonas aeruginosa.
2004-12
2DCOR-GC: an application of the generalized two-dimensional correlation analysis as a route to optimization of continuous flow supercritical fluid reactions.
2004-11-01
Investigations of the reactions of monochloramine and dichloramine with selected phenols: examination of humic acid models and water contaminants.
2004-10-01
Characterization of phenol and trichloroethene degradation by the rhizobium Ralstonia taiwanensis.
2004-10
Protein engineering of toluene 4-monooxygenase of Pseudomonas mendocina KR1 for synthesizing 4-nitrocatechol from nitrobenzene.
2004-09-20
Chromatographic molecular recognition for catechol-related compounds using thiacalix[4]arene as an effective selector.
2004-09
Turbulence effects on volatilization rates of liquids and solutes.
2004-08-15
Exponential modeling, washout curve reconstruction, and estimation of half-life of toluene and its metabolites.
2004-07-23
Isolation and characterization of novel bacteria degrading polycyclic aromatic hydrocarbons from polluted Greek soils.
2004-07
[Hygienic aspects of the impact of solid waste disposal sites on the habitat].
2004-06-17
Crystallographic and solution studies of N-lithocholyl insulin: a new generation of prolonged-acting human insulins.
2004-05-25
Kinetic property and phylogenic relationship of 2-hydroxymuconic semialdehyde dehydrogenase encoded in tomC gene of Burkholderia cepacia G4.
2004-05
[Extraction of 2-methyl-hydroxybenzene and 3-methyl-hydroxybenzene from water solutions].
2004-04-28
Ion transport across model lipid membranes containing light-harvesting complex II: an effect of light.
2004-03-19
Quantitative analysis of cresol and its metabolites in biological materials and distribution in rats after oral administration.
2004-03
Effect of endodontic agents on cytotoxicity induction by sodium fluoride.
2004-02-05
Substrate specificities and electron paramagnetic resonance properties of benzylsuccinate synthases in anaerobic toluene and m-xylene metabolism.
2004-02
Diffusion of Ca(OH)2 associated with different vehicles: chromatographic study (high-performance liquid chromatography).
2004-01
Liquid growth hormone: preservatives and buffers.
2004
Final report on the safety assessment of 6-Amino-m-Cresol, 6-Amino-o-Cresol, 4-Amino-m-Cresol, 5-Amino-4-Chloro-o-Cresol, 5-Amino-6-Chloro-o-Cresol, and 4-Chloro-2-Aminophenol.
2004
A genome annotation-driven approach to cloning the human ORFeome.
2004
Cell-transforming activity of fourteen chemical agents used in dental practice in Syrian hamster embryo cells.
2003-12
Isolation of Brachymonas petroleovorans CHX, a novel cyclohexane-degrading beta-proteobacterium.
2003-10-10
A new variant activator involved in the degradation of phenolic compounds from a strain of Pseudomonas putida.
2003-08-15
Decomposition of 2-bromophenol in NaOH solution at high temperature.
2003-08-01
Ultrasonic and IR study of intermolecular association through hydrogen bonding in ternary liquid mixtures.
2003-08
pH Dependence of the photocycle kinetics of the E46Q mutant of photoactive yellow protein: protonation equilibrium between I1 and I2 intermediates, chromophore deprotonation by hydroxyl uptake, and protonation relaxation of the dark state.
2003-07-29
Optical sensor for carbon dioxide combining colorimetric change of a pH indicator and a reference luminescent dye.
2003-07
The protective effect of M40401, a superoxide dismutase mimetic, on post-ischemic brain damage in Mongolian gerbils.
2003-06-16
[The reactions between acidic phenolsulfonphthaleins and human serum albumin].
2003-06
Identification of aroma active compounds in orange essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry.
2003-05-23
Stability and preservative effectiveness of treprostinil sodium after dilution in common intravenous diluents.
2003-05-01
Higher susceptibility of newborn than young rats to 3-methylphenol.
2003-05
Heteroconjugation-based capillary electrophoretic separation of phenolic compounds in acetonitrile and propylene carbonate.
2003-05
Toxicity and kinetic parameters of the aerobic biodegradation of the phenol and alkylphenols by a mixed culture.
2003-04
Drug intolerance reaction to insulin therapy caused by metacresol.
2003-03
[Spectrophotometry determination of roxithromycin based on charge transfer reaction].
2003-02
Simultaneous biodegradation of a phenol and 3,4-dimethylphenol mixture under denitrifying conditions.
2003
Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques.
2003
Membrane damage to bacteria caused by single and combined biocides.
2003
[Using genetic algorithm for quantitative analysis of overlapped spectra in FTIR].
2001-10
Rapid analysis of pesticide components, xylene, o-dichlorbenzene, cresol and dichlorvos, in blood and urine by pulse heating-gas chromatography-mass spectrometry.
2001-09
Patents

Sample Use Guides

L929 cells were incubated with pure m-cresol in a dose-dependent manner (0–2.5 mg/ml) for 24 h, which revealed the threshold of toxicity at 0.6 mg/ml for m-cresol.
Name Type Language
M-CRESOL
FHFI   INCI   MI   WHO-DD  
INCI  
Preferred Name English
METACRESOL
EP   HSDB   II   USP   USP-RS  
Systematic Name English
NSC-8768
Code English
CRESOL, M-
Systematic Name English
M-METHYLPHENOL
Systematic Name English
METACRESOL [USP MONOGRAPH]
Common Name English
M-CRESYLIC ACID
Common Name English
METACRESOL [USP IMPURITY]
Common Name English
METACRESOL [EP IMPURITY]
Common Name English
3-CRESOL
Systematic Name English
M-cresol [WHO-DD]
Common Name English
METACRESOL [EP MONOGRAPH]
Common Name English
METACRESOL [HSDB]
Common Name English
FEMA NO. 3530
Code English
3-Hydroxytoluene
Systematic Name English
AMYLMETACRESOL IMPURITY B [EP IMPURITY]
Common Name English
PHENOL, 3-METHYL-
Systematic Name English
1-HYDROXY-3-METHYLBENZENE
Systematic Name English
M-KRESOL
Common Name English
3-METHYLPHENOL
Systematic Name English
METACRESOL [II]
Common Name English
1-METHYL-3-HYDROXYBENZENE
Systematic Name English
META-CRESOL
Systematic Name English
METACRESOL [USP-RS]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION M-CRESOL
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
EPA PESTICIDE CODE 22102
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
NCI_THESAURUS C737
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
Code System Code Type Description
CHEBI
17231
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
FDA UNII
GGO4Y809LO
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
HSDB
1815
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
DRUG BANK
DB01776
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
MESH
C042041
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
PUBCHEM
342
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
WIKIPEDIA
M-CRESOL
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
JECFA MONOGRAPH
572
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
SMS_ID
100000078997
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
EVMPD
SUB12532MIG
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
RS_ITEM_NUM
1395204
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
NCI_THESAURUS
C80603
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
CAS
108-39-4
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID6024200
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
MERCK INDEX
m3834
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
203-577-9
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
RXCUI
1367170
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL298312
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
DAILYMED
GGO4Y809LO
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY
NSC
8768
Created by admin on Mon Mar 31 17:33:19 GMT 2025 , Edited by admin on Mon Mar 31 17:33:19 GMT 2025
PRIMARY