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452-86-8,MFCD00002205
Catalog No.:AA003LOW

452-86-8 | 4-Methylcatechol

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003LOW
Chemical Name:
4-Methylcatechol
CAS Number:
452-86-8
Molecular Formula:
C7H8O2
Molecular Weight:
124.1372
MDL Number:
MFCD00002205
SMILES:
Cc1ccc(c(c1)O)O
NSC Number:
17489
Properties
Properties
 
BP:
247.7°C at 760 mmHg  
Form:
Solid  
MP:
67-69 °C(lit.)  
Refractive Index:
1.5425 (estimate)  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
92.9  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
XLogP3:
1.4  

Literature

Title: Nerve sprouting contributes to increased severity of ventricular tachyarrhythmias by upregulating iGluRs in rats with healed myocardial necrotic injury.

Journal: Journal of molecular neuroscience : MN 20121001

Title: H-point curve isolation method for determination of catechol in complex unknown mixtures.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20121001

Title: Polyphenol oxidases in Physcomitrella: functional PPO1 knockout modulates cytokinin-dependent development in the moss Physcomitrella patens.

Journal: Journal of experimental botany 20120901

Title: Intracerebroventricular 4-methylcatechol (4-MC) ameliorates chronic pain associated with depression-like behavior via induction of brain-derived neurotrophic factor (BDNF).

Journal: Cellular and molecular neurobiology 20120801

Title: Laccase activity in soils: considerations for the measurement of enzyme activity.

Journal: Chemosphere 20120801

Title: Molecular interactions of mussel protective coating protein, mcfp-1, from Mytilus californianus.

Journal: Biomaterials 20120201

Title: Ras signaling in NGF reduction and TNF-α-related pancreatic β cell apoptosis in hyperglycemic rats.

Journal: Apoptosis : an international journal on programmed cell death 20120101

Title: Photocatalytic degradation of p-cresol by zinc oxide under UV irradiation.

Journal: International journal of molecular sciences 20120101

Title: Valuable nutrients and functional bioactives in different parts of olive (Olea europaea L.)-a review.

Journal: International journal of molecular sciences 20120101

Title: Characterization of catechol 2,3-dioxygenase from Planococcus sp. strain S5 induced by high phenol concentration.

Journal: Acta biochimica Polonica 20120101

Title: Agonistic effect of polyunsaturated fatty acids (PUFAs) and its metabolites on brain-derived neurotrophic factor (BDNF) through molecular docking simulation.

Journal: Lipids in health and disease 20120101

Title: Optimization of 2,3-dihydroxybiphenyl 1,2-dioxygenase expression and its application for biosensor.

Journal: Bioresource technology 20111101

Title: Evolution of a new bacterial pathway for 4-nitrotoluene degradation.

Journal: Molecular microbiology 20111001

Title: 4-methylcatechol inhibits protein oxidation in meat but not disulfide formation.

Journal: Journal of agricultural and food chemistry 20110928

Title: Extradiol dioxygenase-SiO₂ sol-gel modified electrode for catechol and its derivatives detection.

Journal: Biosensors & bioelectronics 20110715

Title: Thiol-quinone adduct formation in myofibrillar proteins detected by LC-MS.

Journal: Journal of agricultural and food chemistry 20110713

Title: The effect of the buffering capacity of the supporting electrolyte on the electrochemical oxidation of dopamine and 4-methylcatechol in aqueous and nonaqueous solvents.

Journal: Chemistry, an Asian journal 20110606

Title: Natural flavonoids as potential multifunctional agents in prevention of diabetic cataract.

Journal: Interdisciplinary toxicology 20110601

Title: 4-Methylcatechol-induced oxidative stress induces intrinsic apoptotic pathway in metastatic melanoma cells.

Journal: Biochemical pharmacology 20110515

Title: Natural compounds containing a catechol group enhance the formation of Nε-(carboxymethyl)lysine of the Maillard reaction.

Journal: Free radical biology & medicine 20110401

Title: 4-Methlycatechol prevents NGF/p75(NTR)-mediated apoptosis via NGF/TrkA system in pancreatic β cells.

Journal: Neuropeptides 20110401

Title: Degradative potential of Stenotrophomonas strain HPC383 having genes homologous to dmp operon.

Journal: Bioresource technology 20110201

Title: Purification and partial biochemical characterization of polyphenol oxidase from mamey (Pouteria sapota).

Journal: Phytochemistry 20110101

Title: Purification and biochemical characterization of ionically unbound polyphenol oxidase from Musa paradisiaca leaf.

Journal: Preparative biochemistry & biotechnology 20110101

Title: Cloning, characterization and analysis of cat and ben genes from the phenol degrading halophilic bacterium Halomonas organivorans.

Journal: PloS one 20110101

Title: Kinetic cooperativity of tyrosinase. A general mechanism.

Journal: Acta biochimica Polonica 20110101

Title: Improved Laccase Production by Trametes pubescens MB89 in Distillery Wastewaters.

Journal: Enzyme research 20110101

Title: Structure Effect on Antioxidant Activity of Catecholamines toward Singlet Oxygen and Other Reactive Oxygen Species in vitro.

Journal: Journal of clinical biochemistry and nutrition 20101101

Title: Catechol 1,2-dioxygenase from the Gram-positive Rhodococcus opacus 1CP: quantitative structure/activity relationship and the crystal structures of native enzyme and catechols adducts.

Journal: Journal of structural biology 20100601

Title: Rutin metabolites: novel inhibitors of nonoxidative advanced glycation end products.

Journal: Free radical biology & medicine 20100301

Title: A multidisciplinary study of archaeological grape seeds.

Journal: Die Naturwissenschaften 20100201

Title: 4-Methylcatechol-induced heme oxygenase-1 exerts a protective effect against oxidative stress in cultured neural stem/progenitor cells via PI3 kinase/Akt pathway.

Journal: Biomedical research (Tokyo, Japan) 20100201

Title: Discovery of fragment molecules that bind the human peroxiredoxin 5 active site.

Journal: PloS one 20100101

Title: The complete multipartite genome sequence of Cupriavidus necator JMP134, a versatile pollutant degrader.

Journal: PloS one 20100101

Title: Molecular modeling of peroxidase and polyphenol oxidase: substrate specificity and active site comparison.

Journal: International journal of molecular sciences 20100101

Title: Characteristics of lignin from flax shives as affected by extraction conditions.

Journal: International journal of molecular sciences 20100101

Title: Effects of 4-methylcatechol on skin reinnervation: promotion of cutaneous nerve regeneration after crush injury.

Journal: Journal of neuropathology and experimental neurology 20091201

Title: Crystal structure and catalytic mechanism of 4-methylmuconolactone methylisomerase.

Journal: The Journal of biological chemistry 20091120

Title: Catalytic properties of catechol 1,2-dioxygenase from Acinetobacter radioresistens S13 immobilized on nanosponges.

Journal: Dalton transactions (Cambridge, England : 2003) 20090907

Title: Methylcatechol 1,2-dioxygenase of Rhodococcus opacus 6a is a new type of the catechol-cleaving enzyme.

Journal: Biochemistry. Biokhimiia 20090901

Title: Purification and biochemical characterization of polyphenol oxidases from embryogenic and nonembryogenic cotton (Gossypium hirsutum L.) cells.

Journal: Applied biochemistry and biotechnology 20090801

Title: An updated review of tyrosinase inhibitors.

Journal: International journal of molecular sciences 20090601

Title: Differential in vitro inhibition of polyphenoloxidase from a wild edible mushroom Lactarius salmonicolor.

Journal: Journal of enzyme inhibition and medicinal chemistry 20090401

Title: Characterization of catechol derivative removal by lignin peroxidase in aqueous mixture.

Journal: Bioresource technology 20090401

Title: Simple ortho- and para-hydroquinones as compounds neuroprotective against oxidative stress in a manner associated with specific transcriptional activation.

Journal: Biochemical and biophysical research communications 20090206

Title: Production of o-diphenols by immobilized mushroom tyrosinase.

Journal: Journal of biotechnology 20090115

Title: The innate immune and systemic response in honey bees to a bacterial pathogen, Paenibacillus larvae.

Journal: BMC genomics 20090101

Title: Extracellular and intracellular polyphenol oxidases cause opposite effects on sensitivity of Streptomyces to phenolics: a case of double-edged sword.

Journal: PloS one 20090101

Title: Nerve sprouting suppresses myocardial I(to) and I(K1) channels and increases severity to ventricular fibrillation in rat.

Journal: Autonomic neuroscience : basic & clinical 20081215

Title: Interleukin-6 protects against paclitaxel, cisplatin and vincristine-induced neuropathies without impairing chemotherapeutic activity.

Journal: Cancer chemotherapy and pharmacology 20081101

Title: Evidence consistent with the requirement of cresolase activity for suicide inactivation of tyrosinase.

Journal: The Tohoku journal of experimental medicine 20081101

Title: A wounding-induced PPO from cowpea (Vigna unguiculata) seedlings.

Journal: Phytochemistry 20080901

Title: Stopped-flow kinetic study of the aroxyl radical-scavenging action of catechins and vitamin C in ethanol and micellar solutions.

Journal: Journal of agricultural and food chemistry 20080625

Title: Anti-inflammatory effects of catechols in lipopolysaccharide-stimulated microglia cells: inhibition of microglial neurotoxicity.

Journal: European journal of pharmacology 20080624

Title: Ultrasmall c(RGDyK)-coated Fe3O4 nanoparticles and their specific targeting to integrin alpha(v)beta3-rich tumor cells.

Journal: Journal of the American Chemical Society 20080618

Title: Titania sol-gel-derived tyrosinase-based amperometric biosensor for determination of phenolic compounds in water samples. Examination of interference effects.

Journal: Analytical and bioanalytical chemistry 20080601

Title: Binding of catechols to mononuclear titanium(IV) and to 1- and 5-nm TiO2 nanoparticles.

Journal: Inorganic chemistry 20080505

Title: Effects of 4-methylcatechol on spatial memory and depression.

Journal: Neuroreport 20080212

Title: Characterisation by liquid chromatography coupled to electrospray ionisation ion trap mass spectrometry of phloroglucinol and 4-methylcatechol oxidation products to study the reactivity of epicatechin in an apple juice model system.

Journal: Journal of chromatography. A 20080201

Title: Enhancement of cutaneous nerve regeneration by 4-methylcatechol in resiniferatoxin-induced neuropathy.

Journal: Journal of neuropathology and experimental neurology 20080201

Title: Purification and characterization of peroxidase from cauliflower (Brassica oleracea L. var. botrytis) buds.

Journal: Protein and peptide letters 20080101

Title: Polyphenol oxidase from wheat bran is a serpin.

Journal: Acta biochimica Polonica 20080101

Title: Kinetics and mechanism of the reaction between chromium(III) and 3,4-dihydroxy-phenyl-propenoic acid (caffeic acid) in weak acidic aqueous solutions.

Journal: Bioinorganic chemistry and applications 20080101

Title: Biomimetic modeling of copper complexes: a study of enantioselective catalytic oxidation on d-(+)-catechin and L-( - )-epicatechin with copper complexes.

Journal: Bioinorganic chemistry and applications 20080101

Title: Understanding marine mussel adhesion.

Journal: Marine biotechnology (New York, N.Y.) 20071201

Title: Purification and characterization of alkylcatechol 2,3-dioxygenase from butylphenol degradation pathway of Pseudomonas putida MT4.

Journal: Journal of bioscience and bioengineering 20071001

Title: Intradiol pathway of para-cresol conversion by Rhodococcus opacus 1CP.

Journal: Biotechnology journal 20070701

Title: Purification and characterization of catechol 2,3-dioxygenase from the aniline degradation pathway of Acinetobacter sp. YAA and its mutant enzyme, which resists substrate inhibition.

Journal: Bioscience, biotechnology, and biochemistry 20070701

Title: Oxidation of 4-methylcatechol: implications for the oxidation of catecholamines.

Journal: Biochemistry 20070612

Title: Quantitative studies on the formation of phenol/2-furfurylthiol conjugates in coffee beverages toward the understanding of the molecular mechanisms of coffee aroma staling.

Journal: Journal of agricultural and food chemistry 20070516

Title: Polyphenol oxidase from yacon roots (Smallanthus sonchifolius).

Journal: Journal of agricultural and food chemistry 20070321

Title: Quantitative precursor studies on di- and trihydroxybenzene formation during coffee roasting using 'in bean' model experiments and stable isotope dilution analysis.

Journal: Journal of agricultural and food chemistry 20061227

Title: A novel meta-cleavage product hydrolase from Flavobacterium sp. ATCC27551.

Journal: Biochemical and biophysical research communications 20061222

Title: A green method for the electroorganic synthesis of new 1,3-Indandione derivatives.

Journal: Chemical & pharmaceutical bulletin 20061001

Title: Development of a stable isotope dilution analysis with liquid chromatography-tandem mass spectrometry detection for the quantitative analysis of di- and trihydroxybenzenes in foods and model systems.

Journal: Journal of agricultural and food chemistry 20060809

Title: Inhibition of advanced glycation end product formation on collagen by rutin and its metabolites.

Journal: The Journal of nutritional biochemistry 20060801

Title: Calculating molar absorptivities for quinones: application to the measurement of tyrosinase activity.

Journal: Analytical biochemistry 20060401

Title: Formation of strecker aldehydes from polyphenol-derived quinones and alpha-amino acids in a nonenzymic model system.

Journal: Journal of agricultural and food chemistry 20060308

Title: Effects of increased nerve growth factor plasma levels on the expression of TrkA and p75 in rat testicles.

Journal: Journal of anatomy 20060301

Title: p-hydroxylation reactions catalyzed by naphthalene dioxygenase.

Journal: FEMS microbiology letters 20060201

Title: Interleukin-6 attenuates the development of experimental diabetes-related neuropathy.

Journal: Neuropathology : official journal of the Japanese Society of Neuropathology 20060201

Title: Purification and characterization of Ocimum basilicum L. polyphenol oxidase.

Journal: Journal of agricultural and food chemistry 20051228

Title: Immune cascade of Spodoptera litura: cloning, expression, and characterization of inducible prophenol oxidase.

Journal: Biochemical and biophysical research communications 20051111

Title: Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution.

Journal: Free radical biology & medicine 20050915

Title: Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibitory effects of some chemicals on enzyme activity.

Journal: Journal of enzyme inhibition and medicinal chemistry 20050601

Title: Tissue localization of cytokinin dehydrogenase in maize: possible involvement of quinone species generated from plant phenolics by other enzymatic systems in the catalytic reaction.

Journal: Plant & cell physiology 20050501

Title: Structure-activity relationship of the tocopherol-regeneration reaction by catechins.

Journal: Free radical biology & medicine 20050501

Title: Effect of AOT on enzymatic activity of the organic solvent resistant tyrosinase from Streptomyces sp. REN-21 in aqueous solutions and water-in-oil microemulsions.

Journal: Journal of colloid and interface science 20050415

Title: A kinetic study of p-cresol oxidation by quince fruit polyphenol oxidase.

Journal: Journal of agricultural and food chemistry 20050223

Title: Characterization and purification of polyphenol oxidase from artichoke (Cynara scolymus L.).

Journal: Journal of agricultural and food chemistry 20050209

Title: Functional characterization and molecular modeling of methylcatechol 2,3-dioxygenase from o-xylene-degrading Rhodococcus sp. strain DK17.

Journal: Biochemical and biophysical research communications 20050128

Title: The bphC gene-encoded 2,3-dihydroxybiphenyl-1,2-dioxygenase is involved in complete degradation of dibenzofuran by the biphenyl-degrading bacterium Ralstonia sp. SBUG 290.

Journal: Journal of applied microbiology 20050101

Title: Effects of aliphatic acids, furfural, and phenolic compounds on Debaryomyces hansenii CCMI 941.

Journal: Applied biochemistry and biotechnology 20050101

Title: Assessment of catechol induction and glucuronidation in rat liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20041201

Title: The pig caecum model: a suitable tool to study the intestinal metabolism of flavonoids.

Journal: Molecular nutrition & food research 20040901

Title: Comparisons of platinum, gold, palladium and glassy carbon as electrode materials in the design of biosensors for glutamate.

Journal: Biosensors & bioelectronics 20040615

Title: Isolation and characterization of polycyclic aromatic hydrocarbons-degrading Sphingomonas sp. strain ZL5.

Journal: Biodegradation 20040601

Title: Electrochemical performance of diamond thin-film electrodes from different commercial sources.

Journal: Analytical chemistry 20040501

Title: Genes for Mn(II)-dependent NahC and Fe(II)-dependent NahH located in close proximity in the thermophilic naphthalene and PCB degrader, Bacillus sp. JF8: cloning and characterization.

Journal: Microbiology (Reading, England) 20040401

Title: Purification and characterization of tyrosinase from gill tissue of Portabella mushrooms.

Journal: Phytochemistry 20040301

Title: Properties of wheat bran polyphenol oxidase.

Journal: Die Nahrung 20040201

Title: Nitric oxide promotes strong cytotoxicity of phenolic compounds against Escherichia coli: the influence of antioxidant defenses.

Journal: Free radical biology & medicine 20031201

Title: Proteomic analysis of the benzoate degradation pathway in Acinetobacter sp. KS-1.

Journal: Research in microbiology 20031201

Title: Purification of catecholase from Solanum melangena (brinjal).

Journal: Indian journal of biochemistry & biophysics 20031201

Title: Optimization of catechol production by membrane-immobilized polyphenol oxidase: a modeling approach.

Journal: Biotechnology and bioengineering 20030705

Title: In vitro cytotoxicity of 4-methylcatechol in murine tumor cells: induction of apoptotic cell death by extracellular pro-oxidant action.

Journal: The Journal of pharmacology and experimental therapeutics 20030701

Title: Characterization of a novel thermostable Mn(II)-dependent 2,3-dihydroxybiphenyl 1,2-dioxygenase from a polychlorinated biphenyl- and naphthalene-degrading Bacillus sp. JF8.

Journal: The Journal of biological chemistry 20030613

Title: Glucuronuria in the koala.

Journal: Journal of chemical ecology 20030601

Title: p75NTR in the spleen: age-dependent changes, effect of NGF and 4-methylcatechol treatment, and structural changes in p75NTR-deficient mice.

Journal: The anatomical record. Part A, Discoveries in molecular, cellular, and evolutionary biology 20030201

Title: 4-Methylcatechol stimulates phosphorylation of Trk family neurotrophin receptors and MAP kinases in cultured rat cortical neurons.

Journal: Journal of neuroscience research 20021101

Title: Synthesis of water-soluble polymeric prodrugs possessing 4-methylcatechol derivatives by mechanochemical solid-state copolymerization and nature of drug release.

Journal: Chemical & pharmaceutical bulletin 20021101

Title: Capture of a labile substrate by expulsion of water molecules from the active site of nicotinate mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase (CobT) from Salmonella enterica.

Journal: The Journal of biological chemistry 20021025

Title: 15N NMR investigation of the covalent binding of reduced TNT amines to soil humic acid, model compounds, and lignocellulose.

Journal: Environmental science & technology 20020901

Title: Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants.

Journal: Biochimica et biophysica acta 20020808

Title: Sequence analysis and molecular characterization of a nitrocatechol dioxygenase gene from Pseudomonas putida.

Journal: Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20020701

Title: Ferredoxin-mediated reactivation of the chlorocatechol 2,3-dioxygenase from Pseudomonas putida GJ31.

Journal: Archives of microbiology 20020401

Title: Diphenol activation of the monophenolase and diphenolase activities of field bean (Dolichos lablab) polyphenol oxidase.

Journal: Journal of agricultural and food chemistry 20020313

Title: Characterization of catechol glucuronidation in rat liver.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020201

Title: Comparison of antioxidative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20020101

Title: Electrochemical behavior of catechol and 3,4-dihydroxytoluene in acetonitrile at a platinum-disk electrode modified with a tyrosinase containing polyacrylamide film.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20010901

Title: Pyridoxine-induced neuropathy in rats: a sensory neuropathy that responds to 4-methylcatechol.

Journal: Neurobiology of disease 20010801

Title: Biological production of optically active muconolactones by Rhodococcus rhodochrous.

Journal: Applied microbiology and biotechnology 20010801

Title: Properties of diphenolase from Vanilla planifolia (Andr.) shoot primordia cultured in vitro.

Journal: Journal of agricultural and food chemistry 20010701

Title: Characterization of a model compound for the lysine tyrosylquinone cofactor of lysyl oxidase.

Journal: Biochemical and biophysical research communications 20010216

Title: Cloning and expression of thermophilic catechol 1,2-dioxygenase gene (catA) from Streptomyces setonii.

Journal: FEMS microbiology letters 20010205

Title: Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.

Journal: Molecular pharmacology 20010201

Title: Isolation of a benzoate-utilizing Pseudomonas strain from soil and production of catechol from benzoate by transpositional mutants.

Journal: Microbiological research 20010101

Title: Therapeutic effects of aldose reductase inhibitor on experimental diabetic neuropathy through synthesis/secretion of nerve growth factor.

Journal: Experimental neurology 19980601

Title: Classification of catechol 1,2-dioxygenase family: sequence analysis of a gene for the catechol 1,2-dioxygenase showing high specificity for methylcatechols from Gram+ aniline-assimilating Rhodococcus erythropolis AN-13.

Journal: Gene 19970131

Title: Substrate specificity of catechol 2,3-dioxygenase encoded by TOL plasmid pWW0 of Pseudomonas putida and its relationship to cell growth.

Journal: Journal of bacteriology 19941001

Title: 3-Sulphocatechol 2,3-dioxygenase and other dioxygenases (EC 1.13.11.2 and EC 1.14.12.-) in the degradative pathways of 2-aminobenzenesulphonic, benzenesulphonic and 4-toluenesulphonic acids in Alcaligenes sp. strain O-1.

Journal: Microbiology (Reading, England) 19940701

Title: The therapeutic effects of 4-methylcatechol, a stimulator of endogenous nerve growth factor synthesis, on experimental diabetic neuropathy in rats.

Journal: Journal of the neurological sciences 19940301

Title: Evidence for the involvement of multiple pathways in the biodegradation of 1- and 2-methylnaphthalene by Pseudomonas putida CSV86.

Journal: Archives of microbiology 19940101

Title: Immunogenicity studies of a synthetic antigen of alpha methyl dopa.

Journal: Immunopharmacology and immunotoxicology 19931101

Title: Selective inhibitory activity of polyhydroxycarboxylates derived from phenolic compounds against human immunodeficiency virus replication.

Journal: Journal of acquired immune deficiency syndromes 19910101

Title: Identification of cis-diols as intermediates in the oxidation of aromatic acids by a strain of Pseudomonas putida that contains a TOL plasmid.

Journal: Journal of bacteriology 19860601

Title: Okuta A, et al. Construction of chimeric catechol 2,3-dioxygenase exhibiting improved activity against the suicide inhibitor 4-methylcatechol. Appl Environ Microbiol. 2004 Mar;70(3):1804-10.

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Tags:452-86-8 Molecular Formula|452-86-8 MDL|452-86-8 SMILES|452-86-8 4-Methylcatechol |Organic_Building_Blocks