2,4-xylenol
phenol, 2,4-dimethyl-
Identification
| Name | 2,4-xylenol |
| IUPAC | 2,4-dimethylphenol |
| CAS Number | 105-67-9 |
| EINECS | 203-321-6 |
| FDA UNII | 5OD803C081 |
| Molecular Formula | C8 H10 O |
| Molecular Weight | 122.16690000 |
| MDL Number | MFCD00002233 |
| Nikkaji Number | J3.606D |
| Beilstein | 0636244 |
| CoE Number | 11259 |
| XlogP3 | 2.30 (est) |
Regulatory
| DG SANTE Food Flavourings | 04.066 2,4-dimethylphenol |
Physical Properties
| Appearance | yellow to brown liquid or solid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 1.01100 @ 25.00 °C. |
| Refractive Index | 1.53800 @ 20.00 °C. |
| Melting Point | 22.00 to 26.00 °C. @ 760.00 mm Hg |
| Boiling Point | 210.00 to 212.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.129000 mmHg @ 25.00 °C. (est) |
| Flash Point | 203.00 °F. TCC ( 95.00 °C. ) |
| logP (o/w) | 2.300 |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Strength | low |
| Odor Description | at 100.00 %. |
| Taste Description | burnt roasted |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 3200 mg/kg |
| Dermal Toxicity | skin-rat LD50 1040 mg/kg |
| Inhalation Toxicity | inhalation-rat LC > 30 mg/m3 |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.011 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 420 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| Dairy products, excluding products of category 02.0 (01.0) | 0.50000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 0.20000 |
| Edible ices, including sherbet and sorbet (03.0) | 0.50000 |
| Processed fruit (04.1) | 0.40000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 1.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 0.20000 |
| Bakery wares (07.0) | 2.00000 |
| Meat and meat products, including poultry and game (08.0) | 0.20000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 0.20000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 0.30000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 0.50000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 0.20000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 1.00000 |
| Ready-to-eat savouries (15.0) | 2.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 0.40000 |
M&U International LLC
Steady supply & demand
Meeting customers increasing demands at home as well as abroad.
Penta International Corporation
Chemistry innovation
At Penta, our products and services help businesses do business better.
Sigma-Aldrich
Complete Supply Chain
The perfect blend of products and services that bring your creativity to life.
Synerzine, Inc.
Innovation. Customization. Aroma Ingredients.
Synerzine is a leading supplier of flavor and fragrance ingredients.
Vigon International
Passion for Simplicity
Manufacturer and supplier of high quality flavor and fragrance ingredients.
Potential Uses
Natural Occurrence
Synonyms
asym.-m-Xylenol
bacticin
2,4-
dimethyl phenol
2,4-
dimethyl-phenol
2,4-
dimethylphenol
gallex
4-
hydroxy-1,3-dimethylbenzene
1-
hydroxy-2,4-dimethylbenzene
4-
hydroxy-m-xylene
lysol
o-
methyl-p-cresol
phenol, 2,4-dimethyl-
m-
xylenol
meta-
xylenol
xylenol-2 4
US Patents:
3,946,080 - Flavouring and perfuming ingredients
PubMed:
Possible intermediates of Cu(phen)-catalyzed C-O cross-coupling of phenol with an aryl bromide by in situ ESI-MS and EPR studies.
US Patents:
3,952,024 - Furfurylthioacetone
PubMed:
Capabilities and limitations of dispersive liquid-liquid microextraction with solidification of floating organic drop for the extraction of organic pollutants from water samples.
PubMed:
Identification of crude-oil components and microorganisms that cause souring under anaerobic conditions.
PubMed:
The catabolism of 2,4-xylenol and p-cresol share the enzymes for the oxidation of para-methyl group in Pseudomonas putida NCIMB 9866.
PubMed:
Amino modified multi-walled carbon nanotubes/polydimethylsiloxane coated stir bar sorptive extraction coupled to high performance liquid chromatography-ultraviolet detection for the determination of phenols in environmental samples.
PubMed:
[Phenols pollutants in soil and shallow groundwater of a retired refinery site].
PubMed:
An effective strategy for a whole-cell biosensor based on putative effector interaction site of the regulatory DmpR protein.
PubMed:
Assessment of priority phenolic compounds in sediments from an extremely polluted coastal wetland (Lake Maryut, Egypt).
PubMed:
Determination of phenols with ion chromatography-online electrochemical derivatization based on porous electrode-fluorescence detection.
PubMed:
Installation of amine moieties into a polycyclic anodic product derived from 2,4-dimethylphenol.
PubMed:
[Determination of 4 phenols in water by three phase hollow fiber microextraction coupled with high performance liquid chromatography].
PubMed:
Treatment of substituted phenol mixtures in single phase and two-phase solid-liquid partitioning bioreactors.
PubMed:
Dearomatisation of o-xylene by P450BM3 (CYP102A1).
PubMed:
Diversity-oriented synthesis of polycyclic scaffolds by modification of an anodic product derived from 2,4-dimethylphenol.
PubMed:
In vitro metabolism of oxymetazoline: evidence for bioactivation to a reactive metabolite.
PubMed:
Selective determination of 2,4-xylenol by gas chromatography/supersonic jet/resonance-enhanced multiphoton ionization/time-of-flight mass spectrometry.
PubMed:
2,4-Dimethylphenol imprinted polymers as a solid-phase extraction sorbent for class-selective extraction of phenolic compounds from environmental water.
PubMed:
Benzylic and aryl hydroxylations of m-xylene by o-xylene dioxygenase from Rhodococcus sp. strain DK17.
PubMed:
Treatment of municipal solid waste leachate using a submerged anaerobic membrane bioreactor at mesophilic and psychrophilic temperatures: analysis of recalcitrants in the permeate using GC-MS.
PubMed:
Filter-based treatment of leachate from an industrial landfill containing shredder residues of end-of-life vehicles and white goods.
PubMed:
Selective ionization of 2,4-xylenol in mass spectrometry using a tunable laser and supersonic jet technique.
PubMed:
Detection of phenolic compounds in flow systems based on tyrosinase-modified reticulated vitreous carbon electrodes.
PubMed:
Simple and sensitive determination of 2,4-xylenol in surface water samples from river and sea by gas chromatography-mass spectrometry.
PubMed:
An amperometric biosensor based on multiwalled carbon nanotube-poly(pyrrole)-horseradish peroxidase nanobiocomposite film for determination of phenol derivatives.
PubMed:
Effect of humic substances on the Fenton treatment of wastewater at acidic and neutral pH.
PubMed:
Mice recognize recent urine scent marks by the molecular composition.
PubMed:
Chemical oxidation of 2,4-dimethylphenol in soil by heterogeneous Fenton process.
PubMed:
[New efficient producers of fungal laccases].
PubMed:
Laccase-catalyzed removal of 2,4-dimethylphenol from synthetic wastewater: effect of polyethylene glycol and dissolved oxygen.
PubMed:
Multiple-ligand binding in CYP2A6: probing mechanisms of cytochrome P450 cooperativity by assessing substrate dynamics.
PubMed:
Comparison of the effect of phenol and its derivatives on protein and free radical formation in human erythrocytes (in vitro).
PubMed:
Development, validation and application of a method to analyze phenols in water samples by solid phase micro extraction-gas chromatography-flame ionization detector.
PubMed:
A 4-alkyl-substituted analogue of guaiacol shows greater repellency to savannah tsetse (Glossina spp.).
PubMed:
Determination of phenolic compounds in wastewater by liquid-phase microextraction coupled with gas chromatography.
PubMed:
Methylphenols removal from water by low-cost adsorbents.
PubMed:
[New ways to increasing the yield of laccase from Panus tigrinus fungi].
PubMed:
Carbon isotope fractionation of organic contaminants due to retardation on humic substances: implications for natural attenuation studies in aquifers.
PubMed:
The Missoula Valley semivolatile and volatile organic compound study: seasonal average concentrations.
PubMed:
Membrane-assisted solvent extraction of seven phenols combined with large volume injection-gas chromatography-mass spectrometric detection.
PubMed:
Solid-phase microextraction of phenol compounds using a fused-silica fiber coated with beta-cyclodextrin-bonded silica particles.
PubMed:
Ruthenium(II)-tris-bipyridine/titanium dioxide codoped zeolite Y photocatalysts: II. Photocatalyzed degradation of the model pollutant 2,4-xylidine, evidence for percolation behavior.
PubMed:
Degradation of water-insoluble dyes by microperoxidase-11, an effective and stable peroxidative catalyst in hydrophilic organic media.
PubMed:
Molybdenum complexes with linked cycloheptatrienyl-phenolate ligands.
PubMed:
An N,N'-dialkyl-4,4'-bipyridinium-modified titanium-dioxide photocatalyst for water remediation--observation and application of supramolecular effects in photocatalytic degradation of pi-donor organic compounds.
PubMed:
Trace level determination of phenols as pentafluorobenzyl derivatives by gas chromatography-negative-ion chemical ionization mass spectrometry.
PubMed:
Organization and regulation of meta cleavage pathway genes for toluene and o-xylene derivative degradation in Pseudomonas stutzeri OX1.
PubMed:
Determination of Henry's law constants of phenols by pervaporation-flow injection analysis.
PubMed:
Removal of phenols from aqueous solution by XAD-4 resin.
PubMed:
Catalase activity in human erythrocytes: effect of phenoxyherbicides and their metabolites.
PubMed:
Generation of novel bacterial regulatory proteins that detect priority pollutant phenols.
PubMed:
Synthesis and analytical properties of a novel columnar metallomesogenic polymer.
PubMed:
Ligand- and subtype-selective coupling of human alpha-2 adrenoceptors to Ca++ elevation in Chinese hamster ovary cells.
PubMed:
Influence of phenoxyherbicides and their metabolites on the form of oxy- and deoxyhemoglobin of vertebrates.
PubMed:
Effects of creosote compounds on the aerobic bio-degradation of benzene.
PubMed:
The influence of creosote compounds on the aerobic degradation of toluene.
PubMed:
Human cytochrome P450 isoform specificity in the regioselective metabolism of toluene and o-, m- and p-xylene.
PubMed:
A microassay for urinary phenol using capillary gas chromatography and optimised enzymic hydrolysis.
PubMed:
A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1.
PubMed:
Development of an amperometric biosensor for the determination of phenolic compounds in reversed micelles.
PubMed:
Biodegradation of ortho-cresol by a mixed culture of nitrate-reducing bacteria growing on toluene.
PubMed:
Ten and ninety-day toxicity studies of 2,4-dimethylphenol in Sprague-Dawley rats.
PubMed:
Metabolic interaction and disposition of methyl ethyl ketone and m-xylene in rats at single and repeated inhalation exposures.
PubMed:
Anaerobic degradation of cresols by denitrifying bacteria.
PubMed:
Use of polymeric sorbents for the off-line preconcentration of priority pollutant phenols from water for high-performance liquid chromatographic analysis.
PubMed:
In vitro cytotoxicity of organic pollutants to bluegill sunfish (BF-2) cells.
PubMed:
Rat lung and liver cytochrome P-450 isozymes involved in the hydroxylation of m-xylene.
PubMed:
Pharmacologic and genetic studies on the modulatory effects of butylated hydroxytoluene on mouse lung adenoma formation.
PubMed:
Urinalysis of minor metabolites of ethylbenzene and m-xylene.
PubMed:
Urinary disposition of ethylbenzene and m-xylene in man following separate and combined exposure.
PubMed:
Cellular toxicity in Chinese hamster ovary cell cultures. II. A statistical appraisal of sensitivity with the rabbit alveolar macrophage, Syrian hamster embryo, BALB 3T3 mouse, and human neonatal fibroblast cell systems.
PubMed:
Mutagenicity testing in the Salmonella typhimurium assay of phenolic compounds and phenolic fractions obtained from smokehouse smoke condensates.
PubMed:
Metabolic interaction between m-xylene and ethanol.
PubMed:
Metabolism and distribution of 2,4-dimethylphenol in rat.
PubMed:
Effects of phenol, 2,4-dimethylphenol, 2,4-dichlorophenol, and pentachlorophenol on embryo, larval, and early-juvenile fathead minnows (Pimephales promelas).
PubMed:
Antimycoplasmal activity of dimethylphenols in a tracheal explant culture system.
PubMed:
Kinetics of m-xylene in man: Influence of intermittent physical exercise and changing environmental concentrations on kinetics.
PubMed:
Kinetics of m-xylene in man: General features of absorption, distribution, biotransformation and excretion in repetitive inhalation exposure.
PubMed:
Semimicro spectrophotometric determination of nitroglycerine in propellants by use of 2,4-xylenol.
PubMed:
Gas-liquid chromatographic determination of nitrate and nitrite in cheese, ham, fish sausage, cod roes, and salmon roes.
PubMed:
Cross-linking of amino acids by formaldehyde. Preparation and 13C NMR spectra of model compounds.
PubMed:
Bacterial metabolism of para- and meta-xylene: oxidation of the aromatic ring.
PubMed:
A novel mechanism for the NIH-shift.
PubMed:
Arene oxides as intermediates in the metabolism of aromatic substrates: alkyl and oxygen migrations during isomerization of alkylated arene oxides.
PubMed:
Tentative method of analysis for nitrate in atmospheric particulate matter (2,4-xylenol method (1)).
PubMed:
The bacterial metabolism of 2,4-xylenol.