2,6-xylenol

2,6-dimethylphenol

CAS: 576-26-1 C8 H10 O MW: 122.16690000 medicinal burnt

Identification

Name2,6-xylenol
IUPAC2,6-dimethylphenol
CAS Number576-26-1
EINECS209-400-1
FDA UNIII8N0RO87OV
Molecular FormulaC8 H10 O
Molecular Weight122.16690000
MDL NumberMFCD00002240
Nikkaji NumberJ43.458B
Beilstein1446677
CoE Number11261
XlogP32.40 (est)

Regulatory

JECFA Food Flavoring707 2,6-xylenol
DG SANTE Food Flavourings04.042 2,6-dimethylphenol
DG SANTE Food Contact Materials2,6-dimethylphenol
FEMA Number3249
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)576-26-1 ; 2,6-XYLENOL
FDA RegulationFDA PART 177 -- INDIRECT FOOD ADDITIVES: POLYMERS

Physical Properties

Appearance white to yellowish orange solid (est)
Assay 99.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 45.00 to 47.00 °C. @ 760.00 mm Hg
Boiling Point 201.00 to 203.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.221000 mmHg @ 25.00 °C. (est)
Flash Point 173.00 °F. TCC ( 78.33 °C. )
logP (o/w) 2.360
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Description at 0.10 % in propylene glycol.
Taste Description sweet burnt smoky

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 296 mg/kg
Dermal Toxicityskin-rabbit LD50 1000 mg/kg
Inhalation Toxicityinhalation-mammal (species unspecified) LC > 270 mg/m3

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic, flavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for 2,6-xylenol usage levels up to0.0500 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU)1.70 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA)1.00 (μg/capita/day)
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-

Berje Inc.

Where the world comes to its senses

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M&U International LLC

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Penta International Corporation

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Sigma-Aldrich

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Synerzine, Inc.

Innovation. Customization. Aroma Ingredients.

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Vigon International

Passion for Simplicity

Manufacturer and supplier of high quality flavor and fragrance ingredients.

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Potential Uses

None Found

Natural Occurrence

coffee PMC osmanthus absolute @ 0.28% Data whiskey

Synonyms

2,6- dimethyl phenol 2,6- dimethyl-hydroxy-benzene 2,6- dimethyl-phenol 2,6- dimethylphenol 2- hydroxy-1,3-dimethyl benzene 1- hydroxy-2,6-dimethyl benzene 2- hydroxy-m-xylene phenol, 2,6-dimethyl- xylenol-2 6 US Patents: 3,946,080 - Flavouring and perfuming ingredients PubMed: Cyclometalated N-Heterocyclic Carbene Complexes of Ruthenium for Access to Electron-Rich Silylene Complexes That Bind the Lewis Acids CuOTf and AgOTf. US Patents: 3,952,024 - Furfurylthioacetone PubMed: Identification of oxidative coupling products of xylenols arising from laboratory-scale phytoremediation. PubMed: Metal-organic framework UiO-66 coated stainless steel fiber for solid-phase microextraction of phenols in water samples. PubMed: Engineering the expression and characterization of two novel laccase isoenzymes from Coprinus comatus in Pichia pastoris by fusing an additional ten amino acids tag at N-terminus. PubMed: Characterisation of volatile compounds in a smoke flavouring from rice husk. 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: Aluminum complexes incorporating symmetrical and asymmetrical tridentate pincer type pyrrolyl ligands: synthesis, characterization and reactivity study. PubMed: Silane-isocyanide coupling involving 1,1-insertion of XylNC into the Si-H bond of a σ-silane ligand. PubMed: Synthesis, structural characterization and catalytic evaluation of the ring-opening polymerization of discrete five-coordinate alkyl aluminium complexes. PubMed: A computational study on enzymatically driven oxidative coupling of chlorophenols: an indirect dehalogenation reaction. PubMed: Measurement of detergent concentration using 2,6-dimethylphenol in membrane-protein crystallization. PubMed: Heterologous expression and characterization of a novel laccase isoenzyme with dyes decolorization potential from Coprinus comatus. PubMed: 4-Chloropropofol enhances chloride currents in human hyperekplexic and artificial mutated glycine receptors. PubMed: Oxidation of 2,6-dimethylaniline by the Fenton, electro-Fenton and photoelectro-Fenton processes. PubMed: Montmorillonite K-10 clay-catalyzed Ferrier rearrangement of 2-C-hydroxymethyl-d-glycals, 3,4,6-tri-O-alkyl-d-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol: a few unexpected domino transformations. PubMed: Anion exchange induced tunable catalysis properties of an uncommon butterfly-like tetranuclear copper(II) cluster and magnetic characterization. PubMed: The anticonvulsant effects of propofol and a propofol analog, 2,6-diisopropyl-4-(1-hydroxy-2,2,2-trifluoroethyl)phenol, in a 6 Hz partial seizure model. PubMed: Gas-phase phenol methylation over Mg/Me/O (Me = Al, Cr, Fe) catalysts: mechanistic implications due to different acid-base and dehydrogenating properties. PubMed: Cyanation of arenes via iridium-catalyzed borylation. PubMed: Identification of 4-[4-(4-fluoro-phenyl)-thiazol-2-ylamino]-2,6-dimethyl-phenol (KR-33749) as an inhibitor of 5-lipoxygenase with potent antiinflammatory activity. PubMed: Oligochlorophens are potent inhibitors of Bacillus anthracis. PubMed: Mitochondrial biotransformation of omega-(phenoxy)alkanoic acids, 3-(phenoxy)acrylic acids, and omega-(1-methyl-1H-imidazol-2-ylthio)alkanoic acids: a prodrug strategy for targeting cytoprotective antioxidants to mitochondria. PubMed: Chemical oxidation of 2,6-dimethylaniline in the fenton process. PubMed: Chemical oxidation of 2,6-dimethylaniline by electrochemically generated Fenton's reagent. PubMed: Comparative study on determination of antioxidant and membrane activities of propofol and its related compounds. PubMed: Reaction of an oxaruthenacycle with DMAD. Stoichiometric transformations of 2,6-xylenol to allylic phenols and benzopyrans via sp(3) C-H bond cleavage reaction. PubMed: Coupling poly-(methacrylic acid-co-ethylene glycol dimethacrylate) monolith microextraction to capillary electrophoresis for the determination of phenols in water samples. PubMed: Novel multiwalled carbon nanotubes-polyaniline composite film coated platinum wire for headspace solid-phase microextraction and gas chromatographic determination of phenolic compounds. PubMed: Two methods for catalytic generation of reactive enolates promoted by a chiral poly gd complex: application to catalytic enantioselective protonation reactions. PubMed: Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. PubMed: Proton-coupled electron-transfer oxidation of phenols by hexachloroiridate(IV). PubMed: Retention time prediction of compounds in Grob standard mixture for apolar capillary columns in temperature-programmed gas chromatography. PubMed: Selective and stability-indicating methods for the simultaneous determination of mexiletine hydrochloride and/or its related substance: 2,6-dimethylphenol. PubMed: [New promising antioxidants based on 2,6-dimethylphenol]. PubMed: Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: kinetics, mechanism and photoproducts. PubMed: Synthesis of (1-adamantylimido)vanadium(V) complexes containing aryloxo, ketimide ligands: effect of ligand substituents in olefin insertion/metathesis polymerization. PubMed: [New efficient producers of fungal laccases]. PubMed: Versatile scorpionates and new developments in the denticity changes of NNCp hybrid scorpionate/cyclopentadienyl ligands in Sc and Y compounds: from kappa1-Neta5-Cp to kappa2-NNeta5-Cp. PubMed: A catalytic enantioselective conjugate addition of cyanide to enones. PubMed: Selective benzylic C-C coupling catalyzed by a bioinspired dicopper complex. PubMed: Synthesis of dimeric phenol derivatives and determination of in vitro antioxidant and radical scavenging activities. PubMed: Synthesis, magnetic behaviour, and X-ray structures of dinuclear copper complexes with multiple bridges. Efficient and selective catalysts for polymerization of 2,6-dimethylphenol. PubMed: Detailed examination of the degradation of phenol derivatives under oxygen delignification conditions. PubMed: Determination of chlorine dioxide in water by gas chromatography-mass spectrometry. PubMed: Laccase-catalyzed polymerization of two phenolic compounds studied by matrix-assisted laser desorption/ionization time-of-flight and electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry with collision-induced dissociation experiments. PubMed: Tropospheric multiphase chemistry of 2,5- and 2,6-dimethylphenols: determination of the mass accommodation coefficients and the Henry's law constants. PubMed: High-affinity blockade of voltage-operated skeletal muscle sodium channels by 2,6-dimethyl-4-chlorophenol. PubMed: [Inhibitory effects of phenolic ecotoxicants on photobacteria at various pH values]. PubMed: Selective oxidative para C-C dimerization of 2,6-dimethylphenol. PubMed: A comparative study of water soluble 5,10,15,20-tetrakis(2,6-dichloro-3-sulfophenyl)porphyrin and its metal complexes as efficient sensitizers for photodegradation of phenols. PubMed: Structural features of phenol derivatives determining potency for activation of chloride currents via alpha(1) homomeric and alpha(1)beta heteromeric glycine receptors. PubMed: Effects of bisphenol A-related diphenylalkanes on vitellogenin production in male carp (Cyprinus carpio) hepatocytes and aromatase (CYP19) activity in human H295R adrenocortical carcinoma cells. PubMed: Antioxidant activity of propofol and related monomeric and dimeric compounds. PubMed: [Study on cross-linked capillary columns coated with polyphenylenesiloxane]. PubMed: Towards a new concept of lignin condensation in kraft pulping. Initial results. PubMed: Effects of speciation on partitioning of iodine in aqueous biphasic systems and onto ABEC resins. PubMed: Phenol and lactone receptors in the distal sensilla of the Haller's organ in Ixodes ricinus ticks and their possible role in host perception. PubMed: Evaluation of the antioxidant properties of propofol and its nitrosoderivative. comparison with homologue substituted phenols. PubMed: Oxidative polymerization of 2,6-dimethylphenol to form poly(2,6-dimethyl-1,4-phenyleneoxide) in water. PubMed: Luminescence quenching of tris(2,2'-bipyridine)ruthenium(II) by 2,6-dimethylphenol and 4-bromo-2,6-dimethylphenol in sol-gel-processed silicate thin films. PubMed: An improved model for the binding of lidocaine and structurally related local anaesthetics to fast-inactivated voltage-operated sodium channels, showing evidence of cooperativity. PubMed: Depolymerization of poly(2,6-dimethyl-1,4-phenylene oxide) under oxidative conditions. PubMed: Molybdenum-phosphorus triple bond stabilization by ancillary alkoxide ligation: synthesis and structure of a terminal phosphide tris-1-methylcyclohexanoxide complex. PubMed: Glucuronidation of propofol and its analogs by human and rat liver microsomes. PubMed: [Preparation and chromatographic characteristics of linear [60] fullerene polysiloxane stationary phase for capillary gas chromatography]. PubMed: Vibrational analysis of substituted phenols: part II. Transferability of valence force constants. PubMed: Block of voltage-operated sodium channels by 2,6-dimethylphenol, a structural analogue of lidocaine's aromatic tail. PubMed: Chiral proton donor reagents: tin tetrachloride--coordinated optically active binaphthol derivatives. PubMed: Synthesis of Zirconium Aryloxide Complexes Containing Pendent Vinyl Groups. PubMed: Structural requirements of phenol derivatives for direct activation of chloride currents via GABA(A) receptors. PubMed: Determination of phenols in soil by supercritical fluid extraction-capillary electrochromatography. PubMed: Reactivity of "Eu(OiPr)2" with phenols: formation of linear Eu3, square pyramidal Eu5, cubic Eu8, and capped cubic Eu9 polymetallic europium complexes. PubMed: Estimation of glycated hemoglobin by 2,6-dimethylphenol: Sulphuric acid conventional method. PubMed: Anaerobic biodegradability of alkylphenols and fuel oxygenates in the presence of alternative electron acceptors. PubMed: Nitrosation of phenolic compounds: inhibition and enhancement. PubMed: Copper(II)-catalyzed reactions of activated aromatics. PubMed: Effect of acid concentration on chromogen formation from hexoses in sulfuric acid-based reactions. PubMed: Lignin peroxidase-catalyzed oxidation of sulfonated azo dyes generates novel sulfophenyl hydroperoxides. PubMed: Oxidative and non-oxidative metabolism of 4-iodoanisole by rat liver microsomes. PubMed: Cometabolic degradation of o-cresol and 2,6-dimethylphenol by Penicillium frequentans Bi 7/2. PubMed: Modified Jeener solid-echo pulse sequences for the measurement of the proton dipolar spin-lattice relaxation time (T1D) of tissue solid-like macromolecular components. PubMed: Determination of menthol in honey by gas chromatography. PubMed: Potential for carboxylation-dehydroxylation of phenolic compounds by a methanogenic consortium. PubMed: Determination of ten beta-blockers in urine by micellar electrokinetic capillary chromatography. PubMed: Myeloperoxidase catalysed cooxidative metabolism of methimazole: oxidation of glutathione and NADH by free radical intermediates. PubMed: Bacterial metabolism of 2,6-xylenol. PubMed: Laccase-mediated detoxification of phenolic compounds. PubMed: The metabolism of N-acetyl-3,5-dimethyl-p-benzoquinone imine in isolated hepatocytes involves N-deacetylation. PubMed: Acute toxicity of cresols, xylenols, and trimethylphenols to Daphnia magna Straus 1820. PubMed: 2,6-Dimethylphenol: a new metabolite of mexiletine. PubMed: Fatal xylenol self-poisoning. PubMed: Uptake of phenol by Trichosporon cutaneum. PubMed: Evidence for a one-electron mechanism of 2-aminofluorene oxidation by prostaglandin H synthase and horseradish peroxidase. PubMed: [Occurrence of phenolic compounds in the dust of swine stalls and henhouses]. PubMed: Reductive oxygenation of carbon tetrachloride: trichloromethylperoxyl radical as a possible intermediate in the conversion of carbon tetrachloride to electrophilic chlorine. PubMed: [Establishment of the maximum permissible concentration of 2,6-xylenol in the atmosphere]. PubMed: [Changes in the erythrocyte osmotic resistance of rats as affected by 2,6-dimethylphenol in vivo and in vitro]. PubMed: Kinetics and mechanism of hydrolysis of labile quaternary ammonium derivatives of tertiary amines. PubMed: Cutaneous penetration of some hairdyes in the hairless rat. PubMed: Oxidation of carbon tetrachloride, bromotrichloromethane, and carbon tetrabromide by rat liver microsomes to electrophilic halogens. PubMed: Chemical structure of the adducts formed by the oxidation of benzidine in the presence of phenols. PubMed: Solvent effects of flavin electron transfer reactions. PubMed: Antimycoplasmal activity of dimethylphenols in a tracheal explant culture system. PubMed: Inhibition of prostaglandin synthesis in mouse 3T3 fibroblasts and human platelets by substituted phenols. PubMed: [Experimental data on evaluating the toxicity of 2,6-dimethylphenol]. PubMed: [Combined effects of 2,6-dimethylphenol and methanol]. PubMed: Reaction of amide homologs. XVI. Alpha-acetamidoalkylation of beta-naphthol and 2,6-xylenol.