3-methyl catechol

1,2-benzenediol, 3-methyl-

CAS: 488-17-5 C7 H8 O2 MW: 124.13916000

Identification

Name3-methyl catechol
IUPAC3-methylbenzene-1,2-diol
CAS Number488-17-5
EINECS207-672-6
FDA UNII0HUZ4Q9R8C
Molecular FormulaC7 H8 O2
Molecular Weight124.13916000
MDL NumberMFCD00016435
Nikkaji NumberJ46.544E
Beilstein0774602
XlogP31.80 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 68.00 °C. @ 760.00 mm Hg
Boiling Point 241.00 °C. @ 760.00 mm Hg
Flash Point 242.00 °F. TCC ( 116.70 °C. ) (est)
logP (o/w) 1.340 (est)
Soluble in water, 1.648e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintravenous-mouse LD50 56 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07878']

Safety in Use

Categoryinformation only not used for fragrances or flavors
Recommendation for 3-methyl catechol usage levels up tonot for fragrance use.
Recommendation for 3-methyl catechol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in food but not in nature

Synonyms

1,2- benzenediol, 3-methyl- catechol, 3-methyl- 1,2- dihydroxy-3-methylbenzene 2,3- dihydroxytoluene 3- methyl-1,2-benzenediol 3- methyl-1,2-dihydroxybenzene 3- methylbenzene-1,2-diol 3- methylcatechol 3- methylpyrocatechol 2,3- toluenediol PubMed: Enhanced 3-methylcatechol production by Pseudomonas putida TODE1 in a two-phase biotransformation system. PubMed: Selection for growth on 3-nitrotoluene by 2-nitrotoluene-utilizing Acidovorax sp. strain JS42 identifies nitroarene dioxygenases with altered specificities. PubMed: Characterization of polyphenol oxidase activity in Ataulfo mango. PubMed: The effect of substituents on the surface modification of anatase nanoparticles with catecholate-type ligands: a combined DFT and experimental study. PubMed: Degradation of toluene by ortho cleavage enzymes in Burkholderia fungorum FLU100. PubMed: Isotope effects of enzymatic dioxygenation of nitrobenzene and 2-nitrotoluene by nitrobenzene dioxygenase. PubMed: Nontargeted GC-MS approach for volatile profile of toasting in cherry, chestnut, false acacia, and ash wood. PubMed: Characterization of a bifunctional O- and N-glucosyltransferase from Vitis vinifera in glucosylating phenolic compounds and 3,4-dichloroaniline in Pichia pastoris and Arabidopsis thaliana. PubMed: Metagenomic screening for aromatic compound-responsive transcriptional regulators. PubMed: Compound-specific stable carbon isotope ratios of phenols and nitrophenols derivatized with N,O-bis(trimethylsilyl)trifluoroacetamide. PubMed: Effective biochemical decomposition of chlorinated aromatic hydrocarbons with a biocatalyst immobilized on a natural enzyme support. PubMed: Biodegradation of 3-nitrotoluene by Rhodococcus sp. strain ZWL3NT. PubMed: Biomineralization of 3-nitrotoluene by Diaphorobacter species. PubMed: Cyclobotryoxide, a phytotoxic metabolite produced by the plurivorous pathogen Neofusicoccum australe. PubMed: Biotransformation of benzene and toluene to catechols by phenol hydroxylase from Arthrobacter sp. W1. PubMed: Characterization of catechol 2,3-dioxygenase from Planococcus sp. strain S5 induced by high phenol concentration. 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: Degradation of 2-chlorotoluene by Rhodococcus sp. OCT 10. PubMed: Extradiol dioxygenase-SiO₂ sol-gel modified electrode for catechol and its derivatives detection. PubMed: Substrate binding mechanism of a type I extradiol dioxygenase. PubMed: A process optimization for bio-catalytic production of substituted catechols (3-nitrocatechol and 3-methylcatechol. PubMed: Biodegradation of 2-nitrotoluene by Micrococcus sp. strain SMN-1. 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: Methylcatechol 1,2-dioxygenase of Rhodococcus opacus 6a is a new type of the catechol-cleaving enzyme. PubMed: Investigation of peptide reactivity of pro-hapten skin sensitizers using a peroxidase-peroxide oxidation system. PubMed: Genetic and biochemical analyses of chlorobenzene degradation gene clusters in Pandoraea sp. strain MCB032. PubMed: Enzyme-substrate interaction and characterization of a 2,3-dihydroxybiphenyl 1,2-dioxygenase from Dyella ginsengisoli LA-4. PubMed: Anti-inflammatory effects of catechols in lipopolysaccharide-stimulated microglia cells: inhibition of microglial neurotoxicity. PubMed: Response of Pseudomonas putida F1 cultures to fluctuating toluene loads and operational failures in suspended growth bioreactors. 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: A novel solid-liquid two-phase partitioning bioreactor for the enhanced bioproduction of 3-methylcatechol. 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: Bacterial degradation of N,N-diethyl-m-toluamide (DEET): cloning and heterologous expression of DEET hydrolase. PubMed: Quantitative precursor studies on di- and trihydroxybenzene formation during coffee roasting using "in bean" model experiments and stable isotope dilution analysis. PubMed: New insights on toluene biodegradation by Pseudomonas putida F1: influence of pollutant concentration and excreted metabolites. PubMed: Solvent selection for enhanced bioproduction of 3-methylcatechol in a two-phase partitioning bioreactor. PubMed: Electrochemical monitoring of the biodegradation of 2,4-dimethylaniline. 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: Characterization of methylhydroquinone-metabolizing oxygenase genes encoded on plasmid in Burkholderia sp. NF100. PubMed: Diversity of 2,3-dihydroxybiphenyl dioxygenase genes in a strong PCB degrader, Rhodococcus sp. strain RHA1. PubMed: Cloning and sequence analysis of hydroxyquinol 1,2-dioxygenase gene in 2,4,6-trichlorophenol-degrading Ralstonia pickettii DTP0602 and characterization of its product. PubMed: Active site residues controlling substrate specificity in 2-nitrotoluene dioxygenase from Acidovorax sp. strain JS42. PubMed: Description of toluene inhibition of methyl bromide biodegradation in seawater and isolation of a marine toluene oxidizer that degrades methyl bromide. PubMed: Chloromethylmuconolactones as critical metabolites in the degradation of chloromethylcatechols: recalcitrance of 2-chlorotoluene. PubMed: Effects of surface hydrophobicity on the catalytic iron ion retention in the active site of two catechol 1,2-dioxygenase isoenzymes. PubMed: Alpha-subunit positions methionine 180 and glutamate 214 of Pseudomonas stutzeri OX1 toluene-o-xylene monooxygenase influence catalysis. 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: Biotransformation in double-phase systems: physiological responses of Pseudomonas putida DOT-T1E to a double phase made of aliphatic alcohols and biosynthesis of substituted catechols. PubMed: Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing 4-methylresorcinol, methylhydroquinone, and pyrogallol. PubMed: Multiplicity of 2,3-dihydroxybiphenyl dioxygenase genes in the Gram-positive polychlorinated biphenyl degrading bacterium Rhodococcus rhodochrous K37. PubMed: Indene bioconversion by a toluene inducible dioxygenase of Rhodococcus sp. I24. PubMed: Use of 3-hydroxyphenylacetylene for activity-dependent, fluorescent labeling of bacteria that degrade toluene via 3-methylcatechol. PubMed: Model description of bacterial 3-methylcatechol production in one- and two-phase systems. PubMed: Genetic engineering of a highly solvent-tolerant Pseudomonas putida strain for biotransformation of toluene to p-hydroxybenzoate. 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: 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: Metabolism of dichloromethylcatechols as central intermediates in the degradation of dichlorotoluenes by Ralstonia sp. strain PS12. PubMed: Effects of substrate and oxygen loading rates on gas-phase toluene removal in a three-phase biofilm reactor. PubMed: The roles of intermediates in biodegradation of benzene, toluene, and p-xylene by Pseudomonas putida F1. PubMed: Membrane-facilitated bioproduction of 3-methylcatechol in an octanol/water two-phase system. PubMed: High-rate 3-methylcatechol production in Pseudomonas putida strains by means of a novel expression system. PubMed: Integrated bioproduction and extraction of 3-methylcatechol. PubMed: Altering catalytic properties of 3-chlorocatechol-oxidizing extradiol dioxygenase from Sphingomonas xenophaga BN6 by random mutagenesis. PubMed: Cloning and expression of thermophilic catechol 1,2-dioxygenase gene (catA) from Streptomyces setonii. PubMed: A genetically modified solvent-tolerant bacterium for optimized production of a toxic fine chemical. PubMed: Properties of the trihydroxytoluene oxygenase from Burkholderia cepacia R34: an extradiol dioxygenase from the 2,4-dinitrotoluene pathway. PubMed: In vitro cytotoxicity of aromatic aerobic biotransformation products in bluegill sunfish BF-2 cells. PubMed: Catalytic properties of the 3-chlorocatechol-oxidizing 2, 3-dihydroxybiphenyl 1,2-dioxygenase from Sphingomonas sp. strain BN6. PubMed: Adenosylcobalamin-mediated methyl transfer by toluate cis-dihydrodiol dehydrogenase of the TOL plasmid pWW0. PubMed: Conversion of 3-chlorocatechol by various catechol 2,3-dioxygenases and sequence analysis of the chlorocatechol dioxygenase region of Pseudomonas putida GJ31. PubMed: Inactivation of toluene 2-monooxygenase in Burkholderia cepacia G4 by alkynes. PubMed: Modulation of arachidonic acid metabolism by phenols: relation to their structure and antioxidant/prooxidant properties. PubMed: Molecular basis for the stabilization and inhibition of 2, 3-dihydroxybiphenyl 1,2-dioxygenase by t-butanol. PubMed: Purification and preliminary characterization of a serine hydrolase involved in the microbial degradation of polychlorinated biphenyls. PubMed: Purification and characterization of catechol 1,2-dioxygenase from Rhodococcus rhodochrous NCIMB 13259 and cloning and sequencing of its catA gene. PubMed: Purification, characterization, and gene analysis of catechol 2,3-dioxygenase from the aniline-assimilating bacterium Pseudomonas species AW-2. PubMed: Distal cleavage of 3-chlorocatechol by an extradiol dioxygenase to 3-chloro-2-hydroxymuconic semialdehyde. PubMed: Structure of catechol 2,3-dioxygenase gene from Alcaligenes eutrophus 335. PubMed: In vitro cytotoxicity of BTEX metabolites in HeLa cells. PubMed: Cloning and sequence analysis of a catechol 2,3-dioxygenase gene from the nitrobenzene-degrading strain Comamonas sp JS765. PubMed: Characterization of the gene encoding catechol 2,3-dioxygenase from Achromobacter xylosoxidans KF701. PubMed: Cloning of genes involved in carbazole degradation of Pseudomonas sp. strain CA10: nucleotide sequences of genes and characterization of meta-cleavage enzymes and hydrolase. PubMed: Microbial degradation of chloroaromatics: use of the meta-cleavage pathway for mineralization of chlorobenzene. PubMed: Structure of catechol 2,3-dioxygenase gene encoded in TOM plasmid of Pseudomonas cepacia G4. PubMed: Analysis of a new dimeric extradiol dioxygenase from a naphthalenesulfonate-degrading sphingomonad. 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: Cloning and sequencing of the genes encoding 2-nitrotoluene dioxygenase from Pseudomonas sp. JS42. PubMed: Cloning of the genes for and characterization of the early stages of toluene and o-xylene catabolism in Pseudomonas stutzeri OX1. PubMed: Construction and use of recombinant Escherichia coli strains for the synthesis of toluene cis-glycol. PubMed: Characterization of the gene encoding catechol 2,3-dioxygenase of Alcaligenes sp. KF711: overexpression, enzyme purification, and nucleotide sequencing. PubMed: Three-dimensional structures of free form and two substrate complexes of an extradiol ring-cleavage type dioxygenase, the BphC enzyme from Pseudomonas sp. strain KKS102. PubMed: Purification and characterization of toluene 2-monooxygenase from Burkholderia cepacia G4. PubMed: Molecular and biochemical characterization of two meta-cleavage dioxygenases involved in biphenyl and m-xylene degradation by Beijerinckia sp. strain B1. PubMed: Substrate specificity differences between two catechol 2,3-dioxygenases encoded by the TOL and NAH plasmids from Pseudomonas putida. PubMed: Phenol and cresol metabolism in Bacillus pumilus isolated from contaminated groundwater. PubMed: Oxidative release of nitrite from 2-nitrotoluene by a three-component enzyme system from Pseudomonas sp. strain JS42. 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: Functional and structural relationship of various extradiol aromatic ring-cleavage dioxygenases of Pseudomonas origin. PubMed: Metabolism of styrene by Rhodococcus rhodochrous NCIMB 13259. PubMed: The catechol 2,3-dioxygenase gene of Rhodococcus rhodochrous CTM: nucleotide sequence, comparison with isofunctional dioxygenases and evidence for an active-site histidine. 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: Overproduction, purification and properties of 2,3-dihydroxyphenylpropionate 1,2-dioxygenase from Escherichia coli. PubMed: Purification and crystallization of 2,3-dihydroxybiphenyl 1,2-dioxygenase. PubMed: Metabolism of 3-methyldiphenyl ether by Sphingomonas sp. SS31. PubMed: Utilization of 3-chloro-2-methylbenzoic acid by Pseudomonas cepacia MB2 through the meta fission pathway. PubMed: Characterization of catechol 2,3-dioxygenases. PubMed: Degradation of 2-methylaniline in Rhodococcus rhodochrous: cloning and expression of two clustered catechol 2,3-dioxygenase genes from strain CTM. PubMed: Degradation of 2-methylaniline and chlorinated isomers of 2-methylaniline by Rhodococcus rhodochrous strain CTM. 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: Mutants of Pseudomonas cepacia G4 defective in catabolism of aromatic compounds and trichloroethylene. PubMed: Catechol 2,3-oxygenase production by genetically engineered Escherichia coli and its application to catechol determination. PubMed: Simultaneous biodegradation of chlorobenzene and toluene by a Pseudomonas strain. 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: Isolation and partial characterization of an extradiol non-haem iron dioxygenase which preferentially cleaves 3-methylcatechol. PubMed: [Structure correction and synthesis of subspinosin]. PubMed: [Plasmids for biphenyl, chlorobiphenyl and metatoluylate degradation from Pseudomonas putida]. PubMed: Toluene degradation by Pseudomonas putida F1. Nucleotide sequence of the todC1C2BADE genes and their expression in Escherichia coli. PubMed: Novel pathway of toluene catabolism in the trichloroethylene-degrading bacterium g4. 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: Toluene degradation by Pseudomonas putida F1: genetic organization of the tod operon. PubMed: Toluene induction and uptake kinetics and their inclusion in the specific-affinity relationship for describing rates of hydrocarbon metabolism. PubMed: TOL plasmid pWW0 in constructed halobenzoate-degrading Pseudomonas strains: prevention of meta pathway. PubMed: Inhibition of catechol 2,3-dioxygenase from Pseudomonas putida by 3-chlorocatechol. PubMed: Naphthalene metabolism by pseudomonads: purification and properties of 1,2-dihydroxynaphthalene oxygenase. PubMed: In vitro studies of poison oak immunity. II. Effect of urushiol analogues on the human in vitro response. PubMed: Chemical structure and biodegradability of halogenated aromatic compounds. Two catechol 1,2-dioxygenases from a 3-chlorobenzoate-grown pseudomonad. PubMed: Extradiol cleavage of 3-methylcatechol by catechol 1,2-dioxygenase from various microorganisms. PubMed: [Peripheral metabolism of isomeric xylenes by Pseudomonas aeruginosa]. PubMed: Catechol 1,2-dioxygenase from Acinetobacter calcoaceticus: purification and properties. PubMed: Metabolism of resorcinylic compounds by bacteria: orcinol pathway in Pseudomonas putida. PubMed: Metabolism of phenol and cresols by Bacillus stearothermophilus. 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: 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: Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad. Ring-fission, lactonizing and delactonizing enzymes. PubMed: Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad. Preliminary evidence for the metabolic pathway. PubMed: Co-metabolism of methyl- and chloro-substituted catechols by an Achromobacter sp. possessing a new meta-cleaving oxygenase. PubMed: Oxoenoic acids as metabolites in the bacterial degradation of catechols. PubMed: Formation of 2-hydroxy-6-oxo-2, trans-4, trans-heptad-ienoic acid from 3-methylcatechol by a Pseudomonas. PubMed: Metabolism of arylsulphonates by micro-organisms. PubMed: The metabolism of cresols by species of Pseudomonas.