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4-methyl catechol
1,2-benzenediol, 4-methyl- (9CI)

Supplier Sponsors

CAS Number: 452-86-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-214-5
Nikkaji Web:J5.755J
Beilstein Number:0636512
XlogP3:1.40 (est)
Molecular Weight:124.13916000
Formula:C7 H8 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Pubchem Patents:Search
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.12900 @ 25.00 °C.
Boiling Point: 247.70 °C. @ 760.00 mm Hg (est)
Flash Point: 250.00 °F. TCC ( 121.10 °C. ) (est)
logP (o/w): 1.340 (est)
Soluble in:
 water, 2.49e+004 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
BOC Sciences
For experimental / research use only.
4-Methylcatechol 98%
For experimental / research use only.
Penta International
Santa Cruz Biotechnology
For experimental / research use only.
Sigma-Aldrich: Aldrich
For experimental / research use only.
4-Methylcatechol ≥95%
For experimental / research use only.
4-Methylcatechol >98.0%(GC)
Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
natural substances and extractives
Recommendation for 4-methyl catechol usage levels up to:
 not for fragrance use.
Recommendation for 4-methyl catechol flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9958
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
RTECS:UX1915000 for cas# 452-86-8
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9958
Pubchem (sid):134975485
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C06730
HMDB (The Human Metabolome Database):HMDB00873
Export Tariff Code:2907.29.9000
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
Search PMC Picture
1,2-benzenediol, 4-methyl- (9CI)
4-methyl benzene-1,2-diol
4-methyl-1,2-benzene diol


PubMed:Isolation and characterization of two novel halotolerant Catechol 2, 3-dioxygenases from a halophilic bacterial consortium.
PubMed:Characterization of polyphenol oxidase from Cape gooseberry (Physalis peruviana L.) fruit.
PubMed:Laccase oxidation and removal of toxicants released during combustion processes.
PubMed:Influence of the Oxidation States of 4-Methylcatechol and Catechin on the Oxidative Stability of β-Lactoglobulin.
PubMed:Removal of 4-Ethylphenol and 4-Ethylguaiacol with Polyaniline-Based Compounds in Wine-Like Model Solutions and Red Wine.
PubMed:Ruminal degradation of quercetin and its influence on fermentation in ruminants.
PubMed:Beneficial Regulation of Metabolic Profiles by Black Raspberries in Human Colorectal Cancer Patients.
PubMed:Infiltration of chitin by protein coacervates defines the squid beak mechanical gradient.
PubMed:Reactivity of copper-α-synuclein peptide complexes relevant to Parkinson's disease.
PubMed:Oxidative calcium release from catechol.
PubMed:Neurotrophic and antioxidant effects of silymarin comparable to 4-methylcatechol in protection against gentamicin-induced ototoxicity in guinea pigs.
PubMed:Dissociation and reduction of covalent β-lactoglobulin-quinone adducts by dithiothreitol, tris(2-carboxyethyl)phosphine, or sodium sulfite.
PubMed:4-Methylcatechol-induced cell damage in TM4 Sertoli cells.
PubMed:Selection for growth on 3-nitrotoluene by 2-nitrotoluene-utilizing Acidovorax sp. strain JS42 identifies nitroarene dioxygenases with altered specificities.
PubMed:Protection of polyunsaturated oils against ruminal biohydrogenation and oxidation during storage using a polyphenol oxidase containing extract from red clover.
PubMed:Purification and partial biochemical characterization of polyphenol oxidase from mango (Mangifera indica cv. Manila).
PubMed:Experimental and theoretical binding affinity between polyvinylpolypyrrolidone and selected phenolic compounds from food matrices.
PubMed:Selected biochemical properties of polyphenol oxidase in butter lettuce leaves (Lactuca sativa L. var. capitata) elicited with dl-β-amino-n-butyric acid.
PubMed:The effect of substituents on the surface modification of anatase nanoparticles with catecholate-type ligands: a combined DFT and experimental study.
PubMed:Quantification of radicals formed during heating of β-lactoglobulin with glucose in aqueous ethanol.
PubMed:Degradation of toluene by ortho cleavage enzymes in Burkholderia fungorum FLU100.
PubMed:Role of tartaric and malic acids in wine oxidation.
PubMed:Activity of a carboxyl-terminal truncated form of catechol 2,3-dioxygenase from Planococcus sp. S5.
PubMed:4-Methylcatechol prevents derangements of brain-derived neurotrophic factor and TrkB-related signaling in anterior cingulate cortex in chronic pain with depression-like behavior.
PubMed:3,4-Dihydroxytoluene, a metabolite of rutin, inhibits inflammatory responses in lipopolysaccharide-activated macrophages by reducing the activation of NF-κB signaling.
PubMed:Purification and characterization of polyphenol oxidase from jackfruit ( Artocarpus heterophyllus ) bulbs.
PubMed:Parameters that enhance the bacterial expression of active plant polyphenol oxidases.
PubMed:Investigation of solute-solvent interactions in phenol compounds: accurate ab initio calculations of solvent effects on 1H NMR chemical shifts.
PubMed:Influence of a polyphenol-enriched protein powder on exercise-induced inflammation and oxidative stress in athletes: a randomized trial using a metabolomics approach.
PubMed:Promotion of thermal analgesia and neuropeptidergic skin reinnervation by 4-methylcatechol in resiniferatoxin-induced neuropathy.
PubMed:Deuterium isotope effect on the suicide inactivation of tyrosinase in its action on o-diphenols.
PubMed:Chemotherapy-induced bone marrow nerve injury impairs hematopoietic regeneration.
PubMed:Catabolism of 4-alkylphenols by Acinetobacter sp. OP5: genetic organization of the oph gene cluster and characterization of alkylcatechol 2, 3-dioxygenase.
PubMed:Multistep conversion of para-substituted phenols by phenol hydroxylase and 2,3-dihydroxybiphenyl 1,2-dioxygenase.
PubMed:Biomineralization of 3-nitrotoluene by Diaphorobacter species.
PubMed:Phenolic antioxidant scavenging of myosin radicals generated by hypervalent myoglobin.
PubMed:Agonistic effect of polyunsaturated fatty acids (PUFAs) and its metabolites on brain-derived neurotrophic factor (BDNF) through molecular docking simulation.
PubMed:Polyphenol oxidases in Physcomitrella: functional PPO1 knockout modulates cytokinin-dependent development in the moss Physcomitrella patens.
PubMed:H-point curve isolation method for determination of catechol in complex unknown mixtures.
PubMed:Characterization of catechol 2,3-dioxygenase from Planococcus sp. strain S5 induced by high phenol concentration.
PubMed:Influence of phenolic compounds on the mechanisms of pyrazinium radical generation in the Maillard reaction.
PubMed:Laccase activity in soils: considerations for the measurement of enzyme activity.
PubMed:Nerve sprouting contributes to increased severity of ventricular tachyarrhythmias by upregulating iGluRs in rats with healed myocardial necrotic injury.
PubMed:Intracerebroventricular 4-methylcatechol (4-MC) ameliorates chronic pain associated with depression-like behavior via induction of brain-derived neurotrophic factor (BDNF).
PubMed:Molecular interactions of mussel protective coating protein, mcfp-1, from Mytilus californianus.
PubMed:Ras signaling in NGF reduction and TNF-α-related pancreatic β cell apoptosis in hyperglycemic rats.
PubMed:Optimization of 2,3-dihydroxybiphenyl 1,2-dioxygenase expression and its application for biosensor.
PubMed:Isolation, characterization and docking studies of 2,3-dihydroxybiphenyl 1,2-dioxygenase from an activated sludge metagenome.
PubMed:Evolution of a new bacterial pathway for 4-nitrotoluene degradation.
PubMed:Kinetic cooperativity of tyrosinase. A general mechanism.
PubMed:4-methylcatechol inhibits protein oxidation in meat but not disulfide formation.
PubMed:Thiol-quinone adduct formation in myofibrillar proteins detected by LC-MS.
PubMed:Extradiol dioxygenase-SiO₂ sol-gel modified electrode for catechol and its derivatives detection.
PubMed:The effect of the buffering capacity of the supporting electrolyte on the electrochemical oxidation of dopamine and 4-methylcatechol in aqueous and nonaqueous solvents.
PubMed:The Effect of Co-administration of 4-Methylcatechol and Progesterone on Sciatic Nerve Function and Neurohistological Alterations in Streptozotocin-Induced Diabetic Neuropathy in Rats.
PubMed:Purification and biochemical characterization of ionically unbound polyphenol oxidase from Musa paradisiaca leaf.
PubMed:4-Methylcatechol-induced oxidative stress induces intrinsic apoptotic pathway in metastatic melanoma cells.
PubMed:4-Methlycatechol prevents NGF/p75(NTR)-mediated apoptosis via NGF/TrkA system in pancreatic β cells.
PubMed:Natural compounds containing a catechol group enhance the formation of Nε-(carboxymethyl)lysine of the Maillard reaction.
PubMed:Degradative potential of Stenotrophomonas strain HPC383 having genes homologous to dmp operon.
PubMed:Structure Effect on Antioxidant Activity of Catecholamines toward Singlet Oxygen and Other Reactive Oxygen Species in vitro.
PubMed:Purification and partial biochemical characterization of polyphenol oxidase from mamey (Pouteria sapota).
PubMed:Evaluation of genetic and functional diversity of Stenotrophomonas isolates from diverse effluent treatment plants.
PubMed:Catalytic oxygenation of phenols by arthropod hemocyanin, an oxygen carrier protein, from Portunus trituberculatus.
PubMed:4-Methylcatechol-induced heme oxygenase-1 exerts a protective effect against oxidative stress in cultured neural stem/progenitor cells via PI3 kinase/Akt pathway.
PubMed:Modified 3-oxoadipate pathway for the biodegradation of methylaromatics in Pseudomonas reinekei MT1.
PubMed:Controlling the fenton reaction in wine.
PubMed: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.
PubMed:Rutin metabolites: novel inhibitors of nonoxidative advanced glycation end products.
PubMed:Methylcatechol 1,2-dioxygenase of Rhodococcus opacus 6a is a new type of the catechol-cleaving enzyme.
PubMed:Effects of 4-methylcatechol on skin reinnervation: promotion of cutaneous nerve regeneration after crush injury.
PubMed:Crystal structure and catalytic mechanism of 4-methylmuconolactone methylisomerase.
PubMed:Catalytic properties of catechol 1,2-dioxygenase from Acinetobacter radioresistens S13 immobilized on nanosponges.
PubMed:Enzyme-substrate interaction and characterization of a 2,3-dihydroxybiphenyl 1,2-dioxygenase from Dyella ginsengisoli LA-4.
PubMed:Characterization of catechol derivative removal by lignin peroxidase in aqueous mixture.
PubMed:Evidence consistent with the requirement of cresolase activity for suicide inactivation of tyrosinase.
PubMed:Differential in vitro inhibition of polyphenoloxidase from a wild edible mushroom Lactarius salmonicolor.
PubMed:Nerve sprouting suppresses myocardial I(to) and I(K1) channels and increases severity to ventricular fibrillation in rat.
PubMed:Purification and biochemical characterization of polyphenol oxidases from embryogenic and nonembryogenic cotton (Gossypium hirsutum L.) cells.
PubMed:A wounding-induced PPO from cowpea (Vigna unguiculata) seedlings.
PubMed:Monooxygenase activity of Octopus vulgaris hemocyanin.
PubMed:Stopped-flow kinetic study of the aroxyl radical-scavenging action of catechins and vitamin C in ethanol and micellar solutions.
PubMed:Ultrasmall c(RGDyK)-coated Fe3O4 nanoparticles and their specific targeting to integrin alpha(v)beta3-rich tumor cells.
PubMed:Anti-inflammatory effects of catechols in lipopolysaccharide-stimulated microglia cells: inhibition of microglial neurotoxicity.
PubMed:Purification and characterization of peroxidase from cauliflower (Brassica oleracea L. var. botrytis) buds.
PubMed:Effects of 4-methylcatechol on spatial memory and depression.
PubMed:Interleukin-6 protects against paclitaxel, cisplatin and vincristine-induced neuropathies without impairing chemotherapeutic activity.
PubMed:Enhancement of cutaneous nerve regeneration by 4-methylcatechol in resiniferatoxin-induced neuropathy.
PubMed: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.
PubMed:Purification and characterization of alkylcatechol 2,3-dioxygenase from butylphenol degradation pathway of Pseudomonas putida MT4.
PubMed: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.
PubMed:Intradiol pathway of para-cresol conversion by Rhodococcus opacus 1CP.
PubMed:Oxidation of 4-methylcatechol: implications for the oxidation of catecholamines.
PubMed:Quantitative studies on the formation of phenol/2-furfurylthiol conjugates in coffee beverages toward the understanding of the molecular mechanisms of coffee aroma staling.
PubMed:Polyphenol oxidase from yacon roots (Smallanthus sonchifolius).
PubMed:Quantitative precursor studies on di- and trihydroxybenzene formation during coffee roasting using "in bean" model experiments and stable isotope dilution analysis.
PubMed:A gene cluster involved in degradation of substituted salicylates via ortho cleavage in Pseudomonas sp. strain MT1 encodes enzymes specifically adapted for transformation of 4-methylcatechol and 3-methylmuconate.
PubMed:A green method for the electroorganic synthesis of new 1,3-Indandione derivatives.
PubMed: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.
PubMed:Effects of increased nerve growth factor plasma levels on the expression of TrkA and p75 in rat testicles.
PubMed:Interleukin-6 attenuates the development of experimental diabetes-related neuropathy.
PubMed:Formation of strecker aldehydes from polyphenol-derived quinones and alpha-amino acids in a nonenzymic model system.
PubMed:Calculating molar absorptivities for quinones: application to the measurement of tyrosinase activity.
PubMed:p-hydroxylation reactions catalyzed by naphthalene dioxygenase.
PubMed:Characterization of methylhydroquinone-metabolizing oxygenase genes encoded on plasmid in Burkholderia sp. NF100.
PubMed:Purification and characterization of Ocimum basilicum L. polyphenol oxidase.
PubMed:Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibitory effects of some chemicals on enzyme activity.
PubMed:Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution.
PubMed:Mutation of glutamic acid 103 of toluene o-xylene monooxygenase as a means to control the catabolic efficiency of a recombinant upper pathway for degradation of methylated aromatic compounds.
PubMed:Regiospecificity of two multicomponent monooxygenases from Pseudomonas stutzeri OX1: molecular basis for catabolic adaptation of this microorganism to methylated aromatic compounds.
PubMed:Effects of aliphatic acids, furfural, and phenolic compounds on Debaryomyces hansenii CCMI 941.
PubMed:Structure-activity relationship of the tocopherol-regeneration reaction by catechins.
PubMed: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.
PubMed:Chloromethylmuconolactones as critical metabolites in the degradation of chloromethylcatechols: recalcitrance of 2-chlorotoluene.
PubMed:Tissue localization of cytokinin dehydrogenase in maize: possible involvement of quinone species generated from plant phenolics by other enzymatic systems in the catalytic reaction.
PubMed: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.
PubMed:A kinetic study of p-cresol oxidation by quince fruit polyphenol oxidase.
PubMed:Characterization and purification of polyphenol oxidase from artichoke (Cynara scolymus L.).
PubMed:Functional characterization and molecular modeling of methylcatechol 2,3-dioxygenase from o-xylene-degrading Rhodococcus sp. strain DK17.
PubMed:Assessment of catechol induction and glucuronidation in rat liver microsomes.
PubMed:Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone, and methylhydroquinone.
PubMed:Isolation and characterization of polycyclic aromatic hydrocarbons-degrading Sphingomonas sp. strain ZL5.
PubMed:Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing 4-methylresorcinol, methylhydroquinone, and pyrogallol.
PubMed:Toluene 3-monooxygenase of Ralstonia pickettii PKO1 is a para-hydroxylating enzyme.
PubMed:Multiplicity of 2,3-dihydroxybiphenyl dioxygenase genes in the Gram-positive polychlorinated biphenyl degrading bacterium Rhodococcus rhodochrous K37.
PubMed:Electrochemical performance of diamond thin-film electrodes from different commercial sources.
PubMed:Comparisons of platinum, gold, palladium and glassy carbon as electrode materials in the design of biosensors for glutamate.
PubMed: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.
PubMed:Purification and characterization of tyrosinase from gill tissue of Portabella mushrooms.
PubMed:Construction of chimeric catechol 2,3-dioxygenase exhibiting improved activity against the suicide inhibitor 4-methylcatechol.
PubMed:Proteomic analysis of the benzoate degradation pathway in Acinetobacter sp. KS-1.
PubMed:Nitric oxide promotes strong cytotoxicity of phenolic compounds against Escherichia coli: the influence of antioxidant defenses.
PubMed:Glucuronuria in the koala.
PubMed:Optimization of catechol production by membrane-immobilized polyphenol oxidase: a modeling approach.
PubMed:Rational engineering of the regioselectivity of TecA tetrachlorobenzene dioxygenase for the transformation of chlorinated toluenes.
PubMed:In vitro cytotoxicity of 4-methylcatechol in murine tumor cells: induction of apoptotic cell death by extracellular pro-oxidant action.
PubMed:Characterization of a novel thermostable Mn(II)-dependent 2,3-dihydroxybiphenyl 1,2-dioxygenase from a polychlorinated biphenyl- and naphthalene-degrading Bacillus sp. JF8.
PubMed:p75NTR in the spleen: age-dependent changes, effect of NGF and 4-methylcatechol treatment, and structural changes in p75NTR-deficient mice.
PubMed:Synthesis of water-soluble polymeric prodrugs possessing 4-methylcatechol derivatives by mechanochemical solid-state copolymerization and nature of drug release.
PubMed:4-Methylcatechol stimulates phosphorylation of Trk family neurotrophin receptors and MAP kinases in cultured rat cortical neurons.
PubMed:15N NMR investigation of the covalent binding of reduced TNT amines to soil humic acid, model compounds, and lignocellulose.
PubMed:Metabolism of dichloromethylcatechols as central intermediates in the degradation of dichlorotoluenes by Ralstonia sp. strain PS12.
PubMed:Oxidative damage shifts from lipid peroxidation to thiol arylation by catechol-containing antioxidants.
PubMed: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.
PubMed:Monocyclic aromatic hydrocarbon degradation by Rhodococcus sp. strain DK17.
PubMed:Sequence analysis and molecular characterization of a nitrocatechol dioxygenase gene from Pseudomonas putida.
PubMed:Comparison of antioxidative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites.
PubMed:Ferredoxin-mediated reactivation of the chlorocatechol 2,3-dioxygenase from Pseudomonas putida GJ31.
PubMed:Characterization of catechol glucuronidation in rat liver.
PubMed:Electrochemical behavior of catechol and 3,4-dihydroxytoluene in acetonitrile at a platinum-disk electrode modified with a tyrosinase containing polyacrylamide film.
PubMed:Isolation of a benzoate-utilizing Pseudomonas strain from soil and production of catechol from benzoate by transpositional mutants.
PubMed:Biological production of optically active muconolactones by Rhodococcus rhodochrous.
PubMed:Pyridoxine-induced neuropathy in rats: a sensory neuropathy that responds to 4-methylcatechol.
PubMed:Properties of diphenolase from Vanilla planifolia (Andr.) shoot primordia cultured in vitro.
PubMed:Proteolytic activation of latent Paraguaya peach PPO. Characterization of monophenolase activity.
PubMed:Characterization of a model compound for the lysine tyrosylquinone cofactor of lysyl oxidase.
PubMed:Cloning and expression of thermophilic catechol 1,2-dioxygenase gene (catA) from Streptomyces setonii.
PubMed:Fast apple (Malus x domestica) and tobacco (Nicotiana tobacum) leaf polyphenol oxidase activity assay for screening transgenic plants.
PubMed:Partial characterization of peroxidase and polyphenol oxidase activities in blackberry fruits.
PubMed:Latent polyphenol oxidases from sago log (Metroxylon sagu): partial purification, activation, and some properties.
PubMed:Transglycosylation by Streptococcus mutans GS-5 glucosyltransferase-D: acceptor specificity and engineering of reaction conditions.
PubMed:Changes in the expression of the nerve growth factor receptors TrkA and p75LNGR in the rat thymus with ageing and increased nerve growth factor plasma levels.
PubMed:Evidence for diverse oxidations in the catabolism of toluene by Rhodococcus rhodochrous strain OFS.
PubMed:The 1.8 A crystal structure of catechol 1,2-dioxygenase reveals a novel hydrophobic helical zipper as a subunit linker.
PubMed:Properties of the trihydroxytoluene oxygenase from Burkholderia cepacia R34: an extradiol dioxygenase from the 2,4-dinitrotoluene pathway.
PubMed:Inhibition of metallopeptidases by flavonoids and related compounds.
PubMed:In vitro cytotoxicity of aromatic aerobic biotransformation products in bluegill sunfish BF-2 cells.
PubMed:Induction of a physiologically active brain-derived neurotrophic factor in the infant rat brain by peripheral administration of 4-methylcatechol.
PubMed:Partial characterization of polyphenol oxidase activity in raspberry fruits.
PubMed:4-methylcatechol increases brain-derived neurotrophic factor content and mRNA expression in cultured brain cells and in rat brain in vivo.
PubMed:An integrated decoupler for capillary electrophoresis with electrochemical detection: application to analysis of brain microdialysate.
PubMed:Catechol(amine)s as probes of lactoperoxidase catalytic site structure: spectroscopic and modeling studies.
PubMed:4-methylcatechol, a potent inducer of nerve growth factor synthesis, protects spiral ganglion neurons from aminoglycoside ototoxicity--preliminary report.
PubMed:Hydroperoxidase activity of lipoxygenase in the presence of cyclodextrins.
PubMed:Nerve growth factor inducer, 4-methyl catechol, potentiates central sensitization associated with acceleration of spinal glutamate release after mustard oil paw injection in rats.
PubMed:Biochemical and genetic evidence for meta-ring cleavage of 2,4, 5-trihydroxytoluene in Burkholderia sp. strain DNT.
PubMed:Modulation of arachidonic acid metabolism by phenols: relation to their structure and antioxidant/prooxidant properties.
PubMed:The modified beta-ketoadipate pathway in Rhodococcus rhodochrous N75: enzymology of 3-methylmuconolactone metabolism.
PubMed:Quantitative structure/activity relationship for the rate of conversion of C4-substituted catechols by catechol-1,2-dioxygenase from Pseudomonas putida (arvilla) C1.
PubMed:Purification and characterization of catechol 1,2-dioxygenase from Rhodococcus rhodochrous NCIMB 13259 and cloning and sequencing of its catA gene.
PubMed:Therapeutic effects of aldose reductase inhibitor on experimental diabetic neuropathy through synthesis/secretion of nerve growth factor.
PubMed:Stimulatory effects of 4-methylcatechol, dopamine and levodopa on the expression of metallothionein-III (GIF) mRNA in immortalized mouse brain glial cells (VR-2g).
PubMed:Purification, characterization, and gene analysis of catechol 2,3-dioxygenase from the aniline-assimilating bacterium Pseudomonas species AW-2.
PubMed:A novel -2Fe-2S- ferredoxin from Pseudomonas putida mt2 promotes the reductive reactivation of catechol 2,3-dioxygenase.
PubMed:Model sclerotization studies. 4. Generation of N-acetylmethionyl catechol adducts during tyrosinase-catalyzed oxidation of catechols in the presence of N-acetylmethionine.
PubMed:Structure of catechol 2,3-dioxygenase gene from Alcaligenes eutrophus 335.
PubMed:In vitro cytotoxicity of BTEX metabolites in HeLa cells.
PubMed:Characterization of the gene encoding catechol 2,3-dioxygenase from Achromobacter xylosoxidans KF701.
PubMed: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.
PubMed:Synthesis and evaluation of brain-targeted chemical delivery systems for the neurotrophomodulator 4-methylcatechol.
PubMed:2-aminophenol 1,6-dioxygenase: a novel aromatic ring cleavage enzyme purified from Pseudomonas pseudoalcaligenes JS45.
PubMed:Cloning of the genes for and characterization of the early stages of toluene and o-xylene catabolism in Pseudomonas stutzeri OX1.
PubMed:Characterization of the gene encoding catechol 2,3-dioxygenase of Alcaligenes sp. KF711: overexpression, enzyme purification, and nucleotide sequencing.
PubMed:Purification and characterization of a novel type of protocatechuate 3,4-dioxygenase with the ability to oxidize 4-sulfocatechol.
PubMed:Cyclooxygenase induction is essential for NGF synthesis enhancement by NGF inducers in L-M cells.
PubMed:A catechol derivative (4-methylcatechol) accelerates the recovery from experimental acrylamide-induced neuropathy.
PubMed:Characterization of a 2,3-dihydroxybiphenyl dioxygenase from the naphthalenesulfonate-degrading bacterium strain BN6.
PubMed:Antibacterial polyphenols from olive oil mill waste waters.
PubMed:Autoxidation of 4-methylcatechol: a model for the study of the biosynthesis of copper amine oxidases quinonoid cofactor.
PubMed:Characterization by arbitrary primer polymerase chain reaction of polychlorinated biphenyl (PCB)-degrading strains of Comamonas testosteroni isolated from PCB-contaminated soil.
PubMed:Electrophoretical and histochemical characterization of Schistosoma mansoni phenol oxidases.
PubMed:Substrate specificity differences between two catechol 2,3-dioxygenases encoded by the TOL and NAH plasmids from Pseudomonas putida.
PubMed:4-Methylcatechol, an inducer of nerve growth factor synthesis, enhances peripheral nerve regeneration across nerve gaps.
PubMed:High levels of synthesis and local effects of nerve growth factor in the septal region of the adult rat brain.
PubMed:Overexpression of Pseudomonas putida catechol 2,3-dioxygenase with high specific activity by genetically engineered Escherichia coli.
PubMed:Effects of 4-methylcatechol, a stimulator of endogenous nerve growth factor synthesis, on experimental acrylamide-induced neuropathy in rats.
PubMed:Phenol and cresol metabolism in Bacillus pumilus isolated from contaminated groundwater.
PubMed:Informations on the active site of palmito polyphenol oxidase.
PubMed:Localization of phenol oxidase in female Trichuris suis.
PubMed:Prolonged alkylcatechol-induced expression of c-jun proto-oncogene followed by elevation of NGF mRNA in cultured astroglial cells.
PubMed:Substrate specificity of catechol 2,3-dioxygenase encoded by TOL plasmid pWW0 of Pseudomonas putida and its relationship to cell growth.
PubMed:Biodegradation of 2-nitrotoluene by Pseudomonas sp. strain JS42.
PubMed:Screening of depigmenting compounds for the development of an alternate method of branding beef cattle.
PubMed:Direct and mediated effects onBactrocera oleae (Gmelin) (Diptera; Tephritidae) of natural polyphenols and some of related synthetic compounds: Structure-activity relationships.
PubMed:The therapeutic effects of 4-methylcatechol, a stimulator of endogenous nerve growth factor synthesis, on experimental diabetic neuropathy in rats.
PubMed:Carcinogenicity of 4-methoxyphenol and 4-methylcatechol in F344 rats.
PubMed:Evidence for the involvement of multiple pathways in the biodegradation of 1- and 2-methylnaphthalene by Pseudomonas putida CSV86.
PubMed:Immunogenicity studies of a synthetic antigen of alpha methyl dopa.
PubMed:Characterization of 2,2',3-trihydroxybiphenyl dioxygenase, an extradiol dioxygenase from the dibenzofuran- and dibenzo-p-dioxin-degrading bacterium Sphingomonas sp. strain RW1.
PubMed:Pharmacological induction of nerve growth factor mRNA in adult rat brain.
PubMed:Alkylcatechols regulate NGF gene expression in astroglial cells via both protein kinase C- and cAMP-independent mechanisms.
PubMed:In vivo reactivation of catechol 2,3-dioxygenase mediated by a chloroplast-type ferredoxin: a bacterial strategy to expand the substrate specificity of aromatic degradative pathways.
PubMed:Metabolism of p-Cresol by the Fungus Aspergillus fumigatus.
PubMed:The occurrence of phenol oxidase activity in female Trichuris suis.
PubMed:Possible tumor-initiating and -promoting activity of p-methylcatechol and methylhydroquinone in the pyloric mucosa of rat stomach.
PubMed:Purification and crystallization of 2,3-dihydroxybiphenyl 1,2-dioxygenase.
PubMed:Purification and properties of the physically associated meta-cleavage pathway enzymes 4-hydroxy-2-ketovalerate aldolase and aldehyde dehydrogenase (acylating) from Pseudomonas sp. strain CF600.
PubMed:Utilization of aromatic compounds by the Penicillium strain Bi 7/2.
PubMed:Pharmacological induction of physiologically active nerve growth factor in rat peripheral nervous system.
PubMed:Purification and some properties of chlorogenic acid oxidase from apple (Malus pumila).
PubMed:Effects of catechol compound administration on nerve growth factor synthesis in the peripheral nervous system.
PubMed:Metabolism of 3-methyldiphenyl ether by Sphingomonas sp. SS31.
PubMed:Induction of NGF by isoproterenol, 4-methylcatechol and serum occurs by three distinct mechanisms.
PubMed:Characterization of catechol 2,3-dioxygenases.
PubMed:Effect of 4-methylcatechol on sciatic nerve growth factor level and motor nerve conduction velocity in experimental diabetic neuropathic process in rats.
PubMed:Synergism exerted by 4-methyl catechol, catechol, and their respective quinones on the rate of DL-DOPA oxidation by mushroom tyrosinase.
PubMed:Phenoloxidase catalyzed coupling of catechols. Identification of novel coupling products.
PubMed:Studies on the enzymes involved in puparial cuticle sclerotization in Drosophila melanogaster.
PubMed:Genetic organization and regulation of a meta cleavage pathway for catechols produced from catabolism of toluene, benzene, phenol, and cresols by Pseudomonas pickettii PKO1.
PubMed:Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids.
PubMed:Catechol 2,3-oxygenase production by genetically engineered Escherichia coli and its application to catechol determination.
PubMed:Pyrroles as effective agents for blocking amine nitrosation.
PubMed:Lipoxygenase-inhibitory action of antiviral polymeric oxidation products of polyphenols.
PubMed:[Comparative study of aromatic ring meta-cleavage enzymes in Pseudomonas strains with plasmid and chromosomal genetic control of the catabolism of biphenyl and m-toluate].
PubMed:Stimulatory effect of 4-alkylcatechols and their diacetylated derivatives on the synthesis of nerve growth factor.
PubMed:Construction of hybrid xylE genes between the two duplicate homologous genes from TOL plasmid pWW53: comparison of the kinetic properties of the gene products.
PubMed:The effect of substrate partitioning on the kinetics of enzymes acting in reverse micelles.
PubMed:Neurotensin binding to dopamine.
PubMed:Isolation and partial characterization of an extradiol non-haem iron dioxygenase which preferentially cleaves 3-methylcatechol.
PubMed:Initial steps in the degradation of benzene sulfonic acid, 4-toluene sulfonic acids, and orthanilic acid in Alcaligenes sp. strain O-1.
PubMed:[Plasmids for biphenyl, chlorobiphenyl and metatoluylate degradation from Pseudomonas putida].
PubMed:Characteristics of tyrosinase in AOT-isooctane reverse micelles.
PubMed:Novel pathway of toluene catabolism in the trichloroethylene-degrading bacterium g4.
PubMed:A chromogenic assay for catecholoxidases based on the addition of L-proline to quinones.
PubMed:Catecholamines increase nerve growth factor mRNA content in both mouse astroglial cells and fibroblast cells.
PubMed:Molecular cloning of 3-phenylcatechol dioxygenase involved in the catabolic pathway of chlorinated biphenyl from Pseudomonas putida and its expression in Escherichia coli.
PubMed:Transformations of halogenated aromatic aldehydes by metabolically stable anaerobic enrichment cultures.
PubMed:[Synthesis and melanoma inhibiting properties of 4-alkylpyrocatechol-2-O-beta-D-glucopyranosiduronic acids and their esters].
PubMed:[Purification and properties of two enzymes of meta-cleaving the aromatic ring controlled by the biphenyl biodegradation plasmid pBS 241 from Pseudomonas putida].
PubMed:Cooxidation of styrene by horseradish peroxidase and phenols: a biochemical model for protein-mediated cooxidation.
PubMed:Enzymatic oxidation by frog epidermis tyrosinase of 4-methylcatechol and p-cresol. Influence of L-serine.
PubMed:Chemical and enzymatic oxidation of 4-methylcatechol in the presence and absence of L-serine. Spectrophotometric determination of intermediates.
PubMed:Tyrosinase-catalyzed oxidation of dopa and related catechol(amine)s: a kinetic electron spin resonance investigation using spin-stabilization and spin label oximetry.
PubMed:Oxidation of dopamine and 4-methylcatechol at carbon fiber disk electrodes.
PubMed:Purification and properties of 2,3-dihydroxybiphenyl dioxygenase from polychlorinated biphenyl-degrading Pseudomonas pseudoalcaligenes and Pseudomonas aeruginosa carrying the cloned bphC gene.
PubMed:Adaptation of Pseudomonas putida mt-2 to growth on aromatic amines.
PubMed:Identification of cis-diols as intermediates in the oxidation of aromatic acids by a strain of Pseudomonas putida that contains a TOL plasmid.
PubMed:Interaction of several mono- and dihydroxybenzene derivatives of various depigmenting potencies with L-3,4-dihydroxyphenylalanine-melanin.
PubMed:beta-Ketoadipate pathway in Trichosporon cutaneum modified for methyl-substituted metabolites.
PubMed:Rapid reaction studies on the oxygenation reactions of catechol dioxygenase.
PubMed:The origin of urinary aromatic compounds excreted by ruminants. 4. The potential use of urine aromatic acid and phenol outputs as a measure of voluntary food intake.
PubMed:The origin of urinary aromatic compounds excreted by ruminants. 3. The metabolism of phenolic compounds to simple phenols.
PubMed:Quantitative analysis of catechol and 4-methylcatechol in human urine.
PubMed:Synthesis and antitumor activity of cysteinyl-3,4-dihydroxyphenylalanines and related compounds.
PubMed:Inhibition of catechol 2,3-dioxygenase from Pseudomonas putida by 3-chlorocatechol.
PubMed:[Reactions of nascent quinones with methyl beta-alanate in glacial acetic acid and in aqueous solution (author's transl)].
PubMed:Extradiol cleavage of 3-methylcatechol by catechol 1,2-dioxygenase from various microorganisms.
PubMed:Catechol 1,2-dioxygenase from Acinetobacter calcoaceticus: purification and properties.
PubMed:Metabolism of phenol and cresols by Bacillus stearothermophilus.
PubMed:Metabolism of naphthalene, 2-methylnaphthalene, salicylate, and benzoate by Pseudomonas PG: regulation of tangential pathways.
PubMed:Extradiol cleavage of 3-substituted catechols by an intradiol dioxygenase, pyrocatechase, from a Pseudomonad.
PubMed:Pathways for the degradation of m-cresol and p-cresol by Pseudomonas putida.
PubMed:Bacterial metabolism of arylsulfonates: role of meta cleavage in benzene sulfonate oxidation by Pseudomonas testosteroni.
PubMed:The metabolism of vanillin and isovanillin in the rat.
PubMed:Bacterial metabolism of para- and meta-xylene: oxidation of a methyl substituent.
PubMed:Microbial degradation of alkylbenzenesulphonates. Metabolism of homologues of short alkyl-chain length by an Alcaligenes sp.
PubMed:Effect of Phloroglucinol and Resorcinol on the Clingstone Peach Polyphenol Oxidase-catalyzed Oxidation of 4-Methylcatechol.
PubMed:[Aging of the photosynthetic apparatus : III. Variations and characteristics of o-diphenoloxidase activity (Polyphenoloxidase) during aging in vitro of isolated spinach chloroplasts].
PubMed:Dextro-gamma-carboxymethyl-gamma-methyl-delta-alpha-butenolide. A 1,2-ring-fission product of 4-methylcatechol by Pseudomonas desmolyticum.
PubMed:The purification and properties of a ribonucleoenzyme, o-diphenol oxidase, from potatoes.
PubMed:Oxoenoic acids as metabolites in the bacterial degradation of catechols.
PubMed:The metabolism of cresols by species of Pseudomonas.
4-methylcatechol is a metabolite of homoprotocatechuic acid. It is both a substrate and a suicide inhibitor of Catechol 2,3-dioxygenase [EC]. (PMID 15006807) [HMDB]
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