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
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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Determination of urinary ortho- and meta-cresol in humans by headspace SPME gas chromatography/mass spectrometry. | 2005-03-25 |
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| Inhibition of cyclooxygenase activity, platelet aggregation and thromboxane B2 production by two environmental toxicants: m- and o-cresol. | 2005-03-01 |
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| Determination of phenolic compounds by a polyphenol oxidase amperometric biosensor and artificial neural network analysis. | 2005-02-15 |
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| Construction of a radiation hybrid map of chicken chromosome 2 and alignment to the chicken draft sequence. | 2005-02-04 |
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| Effect of toluene and cresols on Na+,K+-ATPase, and serotonin in rat brain. | 2005-02 |
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| Controlling the regiospecific oxidation of aromatics via active site engineering of toluene para-monooxygenase of Ralstonia pickettii PKO1. | 2005-01-07 |
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| Ability of fourteen chemical agents used in dental practice to induce chromosome aberrations in Syrian hamster embryo cells. | 2005-01 |
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| Quantifying individual fruit fly consumption with Anastrepha suspensa (Diptera: Tephritidae). | 2004-12 |
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| Bioremediation of crystal violet using air bubble bioreactor packed with Pseudomonas aeruginosa. | 2004-12 |
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| 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 |
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| Investigations of the reactions of monochloramine and dichloramine with selected phenols: examination of humic acid models and water contaminants. | 2004-10-01 |
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| Characterization of phenol and trichloroethene degradation by the rhizobium Ralstonia taiwanensis. | 2004-10 |
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| Protein engineering of toluene 4-monooxygenase of Pseudomonas mendocina KR1 for synthesizing 4-nitrocatechol from nitrobenzene. | 2004-09-20 |
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| Chromatographic molecular recognition for catechol-related compounds using thiacalix[4]arene as an effective selector. | 2004-09 |
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| Turbulence effects on volatilization rates of liquids and solutes. | 2004-08-15 |
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| Exponential modeling, washout curve reconstruction, and estimation of half-life of toluene and its metabolites. | 2004-07-23 |
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| Isolation and characterization of novel bacteria degrading polycyclic aromatic hydrocarbons from polluted Greek soils. | 2004-07 |
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| [Hygienic aspects of the impact of solid waste disposal sites on the habitat]. | 2004-06-17 |
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| Crystallographic and solution studies of N-lithocholyl insulin: a new generation of prolonged-acting human insulins. | 2004-05-25 |
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| Kinetic property and phylogenic relationship of 2-hydroxymuconic semialdehyde dehydrogenase encoded in tomC gene of Burkholderia cepacia G4. | 2004-05 |
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| [Extraction of 2-methyl-hydroxybenzene and 3-methyl-hydroxybenzene from water solutions]. | 2004-04-28 |
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| Ion transport across model lipid membranes containing light-harvesting complex II: an effect of light. | 2004-03-19 |
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| Quantitative analysis of cresol and its metabolites in biological materials and distribution in rats after oral administration. | 2004-03 |
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| Effect of endodontic agents on cytotoxicity induction by sodium fluoride. | 2004-02-05 |
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| Substrate specificities and electron paramagnetic resonance properties of benzylsuccinate synthases in anaerobic toluene and m-xylene metabolism. | 2004-02 |
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| Diffusion of Ca(OH)2 associated with different vehicles: chromatographic study (high-performance liquid chromatography). | 2004-01 |
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| Liquid growth hormone: preservatives and buffers. | 2004 |
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| 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 |
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| A genome annotation-driven approach to cloning the human ORFeome. | 2004 |
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| Cell-transforming activity of fourteen chemical agents used in dental practice in Syrian hamster embryo cells. | 2003-12 |
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| Isolation of Brachymonas petroleovorans CHX, a novel cyclohexane-degrading beta-proteobacterium. | 2003-10-10 |
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| A new variant activator involved in the degradation of phenolic compounds from a strain of Pseudomonas putida. | 2003-08-15 |
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| Decomposition of 2-bromophenol in NaOH solution at high temperature. | 2003-08-01 |
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| Ultrasonic and IR study of intermolecular association through hydrogen bonding in ternary liquid mixtures. | 2003-08 |
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| 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 |
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| Optical sensor for carbon dioxide combining colorimetric change of a pH indicator and a reference luminescent dye. | 2003-07 |
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| The protective effect of M40401, a superoxide dismutase mimetic, on post-ischemic brain damage in Mongolian gerbils. | 2003-06-16 |
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| [The reactions between acidic phenolsulfonphthaleins and human serum albumin]. | 2003-06 |
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| Identification of aroma active compounds in orange essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry. | 2003-05-23 |
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| Stability and preservative effectiveness of treprostinil sodium after dilution in common intravenous diluents. | 2003-05-01 |
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| Higher susceptibility of newborn than young rats to 3-methylphenol. | 2003-05 |
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| Heteroconjugation-based capillary electrophoretic separation of phenolic compounds in acetonitrile and propylene carbonate. | 2003-05 |
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| Toxicity and kinetic parameters of the aerobic biodegradation of the phenol and alkylphenols by a mixed culture. | 2003-04 |
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| Drug intolerance reaction to insulin therapy caused by metacresol. | 2003-03 |
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| [Spectrophotometry determination of roxithromycin based on charge transfer reaction]. | 2003-02 |
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| Simultaneous biodegradation of a phenol and 3,4-dimethylphenol mixture under denitrifying conditions. | 2003 |
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| Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques. | 2003 |
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| Membrane damage to bacteria caused by single and combined biocides. | 2003 |
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| [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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28962351
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.
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JECFA EVALUATION |
M-CRESOL
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EPA PESTICIDE CODE |
22102
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NCI_THESAURUS |
C737
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17231
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GGO4Y809LO
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1815
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DB01776
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C042041
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342
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M-CRESOL
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572
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100000078997
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1395204
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C80603
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108-39-4
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DTXSID6024200
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m3834
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203-577-9
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1367170
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CHEMBL298312
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GGO4Y809LO
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8768
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SUBSTANCE RECORD