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2,6-xylenol

Chemical Structure

General Material Information

Preferred name 2,6-xylenol
Trivial Name 2,6-Dimethylphenol
Short Description 2,6-dimethylphenol
Formula C8 H10 O
CAS Number 576-26-1
FEMA Number 3249
Flavis Number 4.042
ECHA Number 209-400-1
FDA UNII I8N0RO87OV
Nikkaji Number J43.458B
Beilstein Number 1446677
MDL MFCD00002240
COE Number 11261
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 707 2,6-xylenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 576-26-1 ; 2,6-XYLENOL
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
  • 2,6-Dimethylphenol
  • 1-Hydroxy-2,6-dimethylbenzene
  • NSC 2123
  • D 104339

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2,6-dimethylphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:576-26-1
Pubchem (cid):11335
Pubchem (sid):134976883
Publications by US Patents
3,946,080 - Flavouring and perfuming ingredients
3,952,024 - Furfurylthioacetone
Publications by PubMed
Cyclometalated N-Heterocyclic Carbene Complexes of Ruthenium for Access to Electron-Rich Silylene Complexes That Bind the Lewis Acids CuOTf and AgOTf.
Identification of oxidative coupling products of xylenols arising from laboratory-scale phytoremediation.
Metal-organic framework UiO-66 coated stainless steel fiber for solid-phase microextraction of phenols in water samples.
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.
Characterisation of volatile compounds in a smoke flavouring from rice husk.
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.
Aluminum complexes incorporating symmetrical and asymmetrical tridentate pincer type pyrrolyl ligands: synthesis, characterization and reactivity study.
Silane-isocyanide coupling involving 1,1-insertion of XylNC into the Si-H bond of a σ-silane ligand.
Synthesis, structural characterization and catalytic evaluation of the ring-opening polymerization of discrete five-coordinate alkyl aluminium complexes.
A computational study on enzymatically driven oxidative coupling of chlorophenols: an indirect dehalogenation reaction.
Measurement of detergent concentration using 2,6-dimethylphenol in membrane-protein crystallization.
Heterologous expression and characterization of a novel laccase isoenzyme with dyes decolorization potential from Coprinus comatus.
4-Chloropropofol enhances chloride currents in human hyperekplexic and artificial mutated glycine receptors.
Oxidation of 2,6-dimethylaniline by the Fenton, electro-Fenton and photoelectro-Fenton processes.
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.
Anion exchange induced tunable catalysis properties of an uncommon butterfly-like tetranuclear copper(II) cluster and magnetic characterization.
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.
Gas-phase phenol methylation over Mg/Me/O (Me = Al, Cr, Fe) catalysts: mechanistic implications due to different acid-base and dehydrogenating properties.
Cyanation of arenes via iridium-catalyzed borylation.
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.
Oligochlorophens are potent inhibitors of Bacillus anthracis.
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.
Chemical oxidation of 2,6-dimethylaniline in the fenton process.
Chemical oxidation of 2,6-dimethylaniline by electrochemically generated Fenton's reagent.
Comparative study on determination of antioxidant and membrane activities of propofol and its related compounds.
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.
Coupling poly-(methacrylic acid-co-ethylene glycol dimethacrylate) monolith microextraction to capillary electrophoresis for the determination of phenols in water samples.
Novel multiwalled carbon nanotubes-polyaniline composite film coated platinum wire for headspace solid-phase microextraction and gas chromatographic determination of phenolic compounds.
Two methods for catalytic generation of reactive enolates promoted by a chiral poly gd complex: application to catalytic enantioselective protonation reactions.
Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols.
Proton-coupled electron-transfer oxidation of phenols by hexachloroiridate(IV).
Retention time prediction of compounds in Grob standard mixture for apolar capillary columns in temperature-programmed gas chromatography.
Selective and stability-indicating methods for the simultaneous determination of mexiletine hydrochloride and/or its related substance: 2,6-dimethylphenol.
[New promising antioxidants based on 2,6-dimethylphenol].
Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: kinetics, mechanism and photoproducts.
Synthesis of (1-adamantylimido)vanadium(V) complexes containing aryloxo, ketimide ligands: effect of ligand substituents in olefin insertion/metathesis polymerization.
[New efficient producers of fungal laccases].
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.
A catalytic enantioselective conjugate addition of cyanide to enones.
Selective benzylic C-C coupling catalyzed by a bioinspired dicopper complex.
Synthesis of dimeric phenol derivatives and determination of in vitro antioxidant and radical scavenging activities.
Synthesis, magnetic behaviour, and X-ray structures of dinuclear copper complexes with multiple bridges. Efficient and selective catalysts for polymerization of 2,6-dimethylphenol.
Detailed examination of the degradation of phenol derivatives under oxygen delignification conditions.
Determination of chlorine dioxide in water by gas chromatography-mass spectrometry.
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.
Tropospheric multiphase chemistry of 2,5- and 2,6-dimethylphenols: determination of the mass accommodation coefficients and the Henry's law constants.
High-affinity blockade of voltage-operated skeletal muscle sodium channels by 2,6-dimethyl-4-chlorophenol.
[Inhibitory effects of phenolic ecotoxicants on photobacteria at various pH values].
Selective oxidative para C-C dimerization of 2,6-dimethylphenol.
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.
Structural features of phenol derivatives determining potency for activation of chloride currents via alpha(1) homomeric and alpha(1)beta heteromeric glycine receptors.
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.
Antioxidant activity of propofol and related monomeric and dimeric compounds.
[Study on cross-linked capillary columns coated with polyphenylenesiloxane].
Towards a new concept of lignin condensation in kraft pulping. Initial results.
Effects of speciation on partitioning of iodine in aqueous biphasic systems and onto ABEC resins.
Phenol and lactone receptors in the distal sensilla of the Haller's organ in Ixodes ricinus ticks and their possible role in host perception.
Evaluation of the antioxidant properties of propofol and its nitrosoderivative. comparison with homologue substituted phenols.
Oxidative polymerization of 2,6-dimethylphenol to form poly(2,6-dimethyl-1,4-phenyleneoxide) in water.
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.
An improved model for the binding of lidocaine and structurally related local anaesthetics to fast-inactivated voltage-operated sodium channels, showing evidence of cooperativity.
Depolymerization of poly(2,6-dimethyl-1,4-phenylene oxide) under oxidative conditions.
Molybdenum-phosphorus triple bond stabilization by ancillary alkoxide ligation: synthesis and structure of a terminal phosphide tris-1-methylcyclohexanoxide complex.
Glucuronidation of propofol and its analogs by human and rat liver microsomes.
[Preparation and chromatographic characteristics of linear [60] fullerene polysiloxane stationary phase for capillary gas chromatography].
Vibrational analysis of substituted phenols: part II. Transferability of valence force constants.
Block of voltage-operated sodium channels by 2,6-dimethylphenol, a structural analogue of lidocaine's aromatic tail.
Chiral proton donor reagents: tin tetrachloride--coordinated optically active binaphthol derivatives.
Synthesis of Zirconium Aryloxide Complexes Containing Pendent Vinyl Groups.
Structural requirements of phenol derivatives for direct activation of chloride currents via GABA(A) receptors.
Determination of phenols in soil by supercritical fluid extraction-capillary electrochromatography.
Reactivity of "Eu(OiPr)2" with phenols: formation of linear Eu3, square pyramidal Eu5, cubic Eu8, and capped cubic Eu9 polymetallic europium complexes.
Estimation of glycated hemoglobin by 2,6-dimethylphenol: Sulphuric acid conventional method.
Anaerobic biodegradability of alkylphenols and fuel oxygenates in the presence of alternative electron acceptors.
Nitrosation of phenolic compounds: inhibition and enhancement.
Copper(II)-catalyzed reactions of activated aromatics.
Effect of acid concentration on chromogen formation from hexoses in sulfuric acid-based reactions.
Lignin peroxidase-catalyzed oxidation of sulfonated azo dyes generates novel sulfophenyl hydroperoxides.
Oxidative and non-oxidative metabolism of 4-iodoanisole by rat liver microsomes.
Cometabolic degradation of o-cresol and 2,6-dimethylphenol by Penicillium frequentans Bi 7/2.
Modified Jeener solid-echo pulse sequences for the measurement of the proton dipolar spin-lattice relaxation time (T1D) of tissue solid-like macromolecular components.
Determination of menthol in honey by gas chromatography.
Potential for carboxylation-dehydroxylation of phenolic compounds by a methanogenic consortium.
Determination of ten beta-blockers in urine by micellar electrokinetic capillary chromatography.
Myeloperoxidase catalysed cooxidative metabolism of methimazole: oxidation of glutathione and NADH by free radical intermediates.
Bacterial metabolism of 2,6-xylenol.
Laccase-mediated detoxification of phenolic compounds.
The metabolism of N-acetyl-3,5-dimethyl-p-benzoquinone imine in isolated hepatocytes involves N-deacetylation.
Acute toxicity of cresols, xylenols, and trimethylphenols to Daphnia magna Straus 1820.
2,6-Dimethylphenol: a new metabolite of mexiletine.
Fatal xylenol self-poisoning.
Uptake of phenol by Trichosporon cutaneum.
Evidence for a one-electron mechanism of 2-aminofluorene oxidation by prostaglandin H synthase and horseradish peroxidase.
[Occurrence of phenolic compounds in the dust of swine stalls and henhouses].
Reductive oxygenation of carbon tetrachloride: trichloromethylperoxyl radical as a possible intermediate in the conversion of carbon tetrachloride to electrophilic chlorine.
[Establishment of the maximum permissible concentration of 2,6-xylenol in the atmosphere].
[Changes in the erythrocyte osmotic resistance of rats as affected by 2,6-dimethylphenol in vivo and in vitro].
Kinetics and mechanism of hydrolysis of labile quaternary ammonium derivatives of tertiary amines.
Cutaneous penetration of some hairdyes in the hairless rat.
Oxidation of carbon tetrachloride, bromotrichloromethane, and carbon tetrabromide by rat liver microsomes to electrophilic halogens.
Chemical structure of the adducts formed by the oxidation of benzidine in the presence of phenols.
Solvent effects of flavin electron transfer reactions.
Antimycoplasmal activity of dimethylphenols in a tracheal explant culture system.
Inhibition of prostaglandin synthesis in mouse 3T3 fibroblasts and human platelets by substituted phenols.
[Experimental data on evaluating the toxicity of 2,6-dimethylphenol].
[Combined effects of 2,6-dimethylphenol and methanol].
Reaction of amide homologs. XVI. Alpha-acetamidoalkylation of beta-naphthol and 2,6-xylenol.

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
FDA Substances Added to Food (formerly EAFUS):View
FDA Indirect Additives used in Food Contact Substances:View
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB32150
FooDB:FDB008878
Export Tariff Code:2907.19.8000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•pitt-consol xylenol 235 is a synthetic 2,6-xylenol. homolog distribution, wt%: ortho cresol, 0.5; 2,6-xylenols, 92; 2,42,5 xylenols, 0.5; metapara cresol, 7. •grade or purity: 99% •pitt-consol xylenol 410 is a synthetic xylenol blend homolog distribution, wt %: 2,6-xylenol, 1; 2,4-xylenol, 42; 2,5-xylenol, 43; 2,3-xylenol group, 14. xylenol 410

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 122.16690063477
Melting Point 45 to 47°C @ 760 mm Hg
Boiling Point 201 to 203°C @ 760 mm Hg
Vapor Pressure 0.221 mmHg @ 25 °C
Flash Point TCC Value 78.33 °C TCC
logP (o/w) 2.36
Solubility
alcohol Yes
water, 3615 mg/L @ 25 °C (est) Yes
water, 6050 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Medicinal
sweet, medicinal, phenolic, rooty, coffee
General comment At 0.10 % in propylene glycol. sweet medicinal phenolic rooty coffee
Flavor Type: Burnt
sweet, burnt, smoky
General comment Sweet burnt smoky

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
T N - Toxic, Dangerous for the environment.
R 24/25 - Toxic in contact with skin and if swallowed.
R 34 - Causes burns.
R 51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S 01/02 - Keep locked up and out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
S 45 - In case of accident or if you feel unwell seek medical advice immediately.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
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:
oral-rat LD50 296 mg/kg
(Maazik, 1968)

oral-rabbit LD50 700 mg/kg
(Maazik, 1968)

oral-mouse LD50 450 mg/kg
(Larionov, 1976)

intraperitoneal-mouse LD50 150 mg/kg
National Technical Information Service. Vol. AD691-490

oral-rat LD50 406 mg/kg
(Larionov, 1976)

oral-mouse LD50 479 mg/kg
(Maazik, 1968)

intravenous-mouse LD50 80 mg/kg
BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: SLEEP
Journal of Medicinal Chemistry. Vol. 23, Pg. 1350, 1980.

oral-mouse LD50 450 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(4), Pg. 43, 1976.

oral-rabbit LD50 700 mg/kg
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA
Hygiene and Sanitation Vol. 33(7-9), Pg. 329, 1968.

oral-rat LD50 296 mg/kg
Gigiena Truda i Professional'naya Patologiya v Estonskoi SSR. Labor Hygiene and Occupational Pathology in the Estonian SSR. Vol. 8, Pg. 145, 1972.

Dermal Toxicity:
skin-rabbit LD50 1000 mg/kg
Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. Vol. 6, Pg. 1, 1967.

skin-rat LD50 2325 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(4), Pg. 43, 1976.

skin-mouse LD50 920 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 58, 1974.

Inhalation Toxicity:
inhalation-mammal (species unspecified) LC > 270 mg/m3
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(4), Pg. 43, 1976.

Safety in use information

Category:
cosmetic, flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 2,6-xylenol usage levels up to:
0.0500 % 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)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 4
Click here to view publication 4
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): -1.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: -1.00000
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: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring-substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 58 (FGE.58) Consideration of phenol derivatives evaluated by JECFA (55th meeting) structurally related to ring substituted phenolic substances evaluated by EFSA in FGE.22 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring- substituted phenolic substances evaluated by EFSA in FGE.22 (2006)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25
View page or View pdf

Scientific Opinion on the safety and efficacy of phenol derivatives containing ring-alkyl, ring-alkoxy and side-chains with an oxygenated functional group (chemical group 25) when used as flavourings for all species
View page or View pdf

EPI System: View
EPA-Iris:IRIS
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):576-26-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11335
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2261
WGK Germany:2
2,6-dimethylphenol
Chemidplus:0000576261
EPA/NOAA CAMEO:hazardous materials
RTECS:ZE6125000 for cas# 576-26-1