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3-methyl catechol
1,2-benzenediol, 3-methyl-

Supplier Sponsors

Name:3-methylbenzene-1,2-diol
CAS Number: 488-17-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-672-6
FDA UNII: 0HUZ4Q9R8C
Nikkaji Web:J46.544E
Beilstein Number:0774602
MDL:MFCD00016435
XlogP3:1.80 (est)
Molecular Weight:124.13916000
Formula:C7 H8 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "odor"Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
3-Methylcatechol
Santa Cruz Biotechnology
For experimental / research use only.
3-Methylcatechol ≥98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
3-Methylcatechol 98%
TCI AMERICA
For experimental / research use only.
3-Methylcatechol >99.0%(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
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-mouse LD50 56 mg/kg
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07878

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for 3-methyl catechol usage levels up to:
 not for fragrance use.
 
Recommendation for 3-methyl catechol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):488-17-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :340
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3-methylbenzene-1,2-diol
Chemidplus:0000488175
RTECS:UX1910000 for cas# 488-17-5
 
References:
 3-methylbenzene-1,2-diol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):340
Pubchem (sid):134976084
 
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
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C02923
HMDB (The Human Metabolome Database):Search
FooDB:FDB000357
Export Tariff Code:2907.29.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 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
 

Articles:

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.
 
Notes:
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