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2,5-xylenol

Chemical Structure

General Material Information

Preferred name 2,5-xylenol
Trivial Name 2,5-Dimethylphenol
Short Description 2,5-dimethylphenol
Formula C8 H10 O
CAS Number 95-87-4
FEMA Number 3595
Flavis Number 4.019
ECHA Number 202-461-5
FDA UNII XH3E3564KX
Nikkaji Number J43.459K
Beilstein Number 1099260
MDL MFCD00002237
COE Number 537
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 706 2,5-xylenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 95-87-4 ; 2,5-XYLENOL
Synonyms
  • 2,5-dimethyl phenol
  • 3,6-dimethyl phenol
  • 1,4-dimethyl-2-hydroxybenzene
  • 2,5-dimethyl-phenol
  • 2,5-dimethylbenzolol
  • 2,5-dimethylphenol
  • 1-hydroxy-2,5-dimethyl benzene
  • 2-hydroxy-p-xylene
  • phenol, 2,5-dimethyl-
  • p- xylenol
  • 2,5-Dimethylphenol
  • p-Xylenol
  • 1,2,5-Xylenol
  • 1-Hydroxy-2,5-dimethylbenzene
  • 3,6-Dimethylphenol
  • NSC 2599
  • 2-Hydroxy-p-xylene

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

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Perfumer & Flavorists Start search
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Literature & References

2,5-dimethylphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:95-87-4
Pubchem (cid):7267
Pubchem (sid):134972199
Publications by US Patents
3,946,080 - Flavouring and perfuming ingredients
3,952,024 - Furfurylthioacetone
Publications by PubMed
Defensive secretions of the carabid beetle Chlaenius cordicollis: chemical components and their geographic patterns of variation.
Prompt HO2 formation following the reaction of OH with aromatic compounds under atmospheric conditions.
Agarose-gel-immobilized recombinant bacterial biosensors for simple and disposable on-site detection of phenolic compounds.
Solid-phase extraction of antipyrine dye for spectrophotometric determination of phenolic compounds in water.
Selective determination of 2,4-xylenol by gas chromatography/supersonic jet/resonance-enhanced multiphoton ionization/time-of-flight mass spectrometry.
A simple HPLC-fluorescence method for quantitation of curcuminoids and its application to turmeric products.
Tropospheric multiphase chemistry of 2,5- and 2,6-dimethylphenols: determination of the mass accommodation coefficients and the Henry's law constants.
Molecular and biochemical characterization of the xlnD-encoded 3-hydroxybenzoate 6-hydroxylase involved in the degradation of 2,5-xylenol via the gentisate pathway in Pseudomonas alcaligenes NCIMB 9867.
Molecular characterization of an inducible gentisate 1,2-dioxygenase gene, xlnE, from Pseudomonas alcaligenes NCIMB 9867.
A new variant activator involved in the degradation of phenolic compounds from a strain of Pseudomonas putida.
Toxicity and kinetic parameters of the aerobic biodegradation of the phenol and alkylphenols by a mixed culture.
Glucuronidation of propofol and its analogs by human and rat liver microsomes.
Determination of estrogenic activity in landfill leachate by simplified yeast two-hybrid assay.
Microcosm studies of microbial degradation in a coal tar distillate plume.
Organization and regulation of meta cleavage pathway genes for toluene and o-xylene derivative degradation in Pseudomonas stutzeri OX1.
Threonine 201 in the diiron enzyme toluene 4-monooxygenase is not required for catalysis.
Group II intron from Pseudomonas alcaligenes NCIB 9867 (P25X): entrapment in plasmid RP4 and sequence analysis.
Transformations of Aromatic Compounds by Nitrosomonas europaea.
A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1.
Concentrations of phenol, o-cresol, and 2,5-xylenol in the urine of workers employed in the distillation of the phenolic fraction of tar.
Effect of p-xylene metabolites, p-methylbenzyl alcohol and 2,5-dimethylphenol, on rat hepatic and pulmonary microsomal metabolism.
Gas chromatographic determination of cresols in the biological fluids of a non-fatal case of cresol intoxication.
Acute toxicity of cresols, xylenols, and trimethylphenols to Daphnia magna Straus 1820.
Regulation of isofunctional enzymes in Pseudomonas alcaligenes mutants defective in the gentisate pathway.
Separation and determination of phenol, alpha-naphthol m- and p-, o-cresols and 2,5-xylenol, and catechol in the urine after mixed exposure to phenol, naphthalene, cresols, and xylenols.
A kinetic colorimetric assay of gamma-glutamyltransferase.
Evidence for isofunctional enzymes used in m-cresol and 2,5-xylenol degradation via the gentisate pathway in Pseudomonas alcaligenes.
Bacterial metabolism of para- and meta-xylene: oxidation of the aromatic ring.
A novel mechanism for the NIH-shift.
The enzymic degradation of alkyl-substituted gentisates, maleates and malates.
Gentisic acid and its 3- and 4-methyl-substituted homologoues as intermediates in the bacterial degradation of m-cresol, 3,5-xylenol and 2,5-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
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB30540
FooDB:FDB002413
Export Tariff Code:2907.19.6100
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Formulations/Preparations:
•xylenol 100; a high purity fraction of 2,4- and 2,5- xylenol (ortho xylenols); typical composition: 2,4- and 2,5-xylenol 93%; meta para cresol 2%; other xylenols 5%. from table •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
Specific gravity @ 25 °C
Pounds per Gallon
Melting Point 75 to 77°C @ 760 mm Hg
Boiling Point 211 to 212°C @ 760 mm Hg
Vapor Pressure 0.128 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 2.33
Solubility
alcohol Yes
water, 3835 mg/L @ 25 °C (est) Yes
water, 3540 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Phenolic
sweet, naphthyl, phenolic, smoky, bacon
General comment At 0.10 % in propylene glycol. sweet naphthyl phenolic smoke bacon
Mosciano, Gerard P&F 15, No. 1, 19, (1990) Sweet, naphthyl, phenolic, smoke, bacon and Iysol-like
Flavor Type: Musty
musty, chemical, stringent, phenolic
Mosciano, Gerard P&F 15, No. 1, 19, (1990) At 10.00 ppm. Musty, chemical, stringent and phenolic

Occurrences

Potential Uses

Applications
Flavoring purposes Bacon, Smoke
Cosmetic purposes Perfuming agents

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 444 mg/kg
(Maazik, 1968)

oral-rabbit LD50 938 mg/kg
(Maazik, 1968)

oral-mouse LD50 383 mg/kg
(Maazik, 1968)

gavage-rat LD50 (De Cresente, 1982)

oral-mouse LD50 383 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-rabbit LD50 938 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: ATAXIA
Hygiene and Sanitation Vol. 33(7-9), Pg. 329, 1968.

oral-rat LD50 444 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.

unreported-rat LD50 730 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 53, Pg. 227, 1935.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
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
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.49 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.03 (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: 11
Click here to view publication 11
average usual ppmaverage maximum ppm
baked goods: -4.00000
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: -2.00000
hard candy: --
imitation dairy: --
instant coffee / tea: -2.00000
jams / jellies: --
meat products: -2.00000
milk products: --
nut products: -2.00000
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: -2.00000
snack foods: --
soft candy: --
soups: -2.00000
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

Safety and efficacy of eight compounds belonging to different chemical groups when used as flavourings for cats and dogs
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):95-87-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7267
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2261
WGK Germany:3
2,5-dimethylphenol
Chemidplus:0000095874
EPA/NOAA CAMEO:hazardous materials
RTECS:ZE5775000 for cas# 95-87-4