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3,4-xylenol

Chemical Structure

General Material Information

Preferred name 3,4-xylenol
Trivial Name 3,4-Dimethylphenol
Short Description 3,4-dimethylphenol
Formula C8 H10 O
CAS Number 95-65-8
FEMA Number 3596
Flavis Number 4.048
ECHA Number 202-439-5
FDA UNII 4L479F5JU6
Nikkaji Number J43.457D
Beilstein Number 1099267
MDL MFCD00002304
COE Number 11262
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 708 3,4-xylenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 95-65-8 ; 3,4-XYLENOL
Synonyms
  • 3,4-dimethyl phenol
  • 1,2-dimethyl-4-hydroxybenzene
  • 3,4-dimethyl-phenol
  • 3,4-dimethylbenzolol
  • 3,4-dimethylphenol
  • 3,4-DMP
  • 4-hydroxy-1,2-dimethyl benzene
  • 1-hydroxy-3,4-dimethyl benzene
  • 1-hydroxy-3,4-dimethylbenzene
  • 4-hydroxy-o-xylene
  • phenol, 3,4-dimethyl-
  • 1,3,4-xylenol
  • 3,4-Dimethylphenol
  • 4,5-Dimethylphenol
  • 4-Hydroxy-1,2-dimethylbenzene
  • 1,3,4-Xylenol
  • 1-Hydroxy-3,4-dimethylbenzene
  • NSC 1549
  • 3,4-DMP

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

Google Scholar Start search
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Literature & References

3,4-dimethylphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:95-65-8
Pubchem (cid):7249
Pubchem (sid):134971891
Publications by US Patents
3,946,080 - Flavouring and perfuming ingredients
3,952,024 - Furfurylthioacetone
Publications by PubMed
Synthesis and characterization of phenolic Mannich bases and effects of these compounds on human carbonic anhydrase isozymes I and II.
Design and synthesis of a vialinin A analog with a potent inhibitory activity of TNF-α production and its transformation into a couple of bioprobes.
Defensive secretions of the carabid beetle Chlaenius cordicollis: chemical components and their geographic patterns of variation.
Isolation of a phenol-utilizing marine bacterium from Durban Harbour (South Africa) and its preliminary characterization as Marinobacter sp. KM2.
Synthesis and blocking activities of isoindolinone- and isobenzofuranone-containing phenoxylalkylamines as potent α(1)-adrenoceptor antagonists.
Biodegradation of phenolic mixtures in a sequencing batch reactor. A kinetic study.
Determination of phenolic compounds in wastewater by liquid-phase microextraction coupled with gas chromatography.
Analysis of bioavailable phenols from natural samples by recombinant luminescent bacterial sensors.
Development of a high analytical performance-tyrosinase biosensor based on a composite graphite-Teflon electrode modified with gold nanoparticles.
Regiospecificity of two multicomponent monooxygenases from Pseudomonas stutzeri OX1: molecular basis for catabolic adaptation of this microorganism to methylated aromatic compounds.
Influence of sodium benzoate on the metabolism of o-xylene in the rat.
Identification of a novel dioxygenase involved in metabolism of o-xylene, toluene, and ethylbenzene by Rhodococcus sp. strain DK17.
Simultaneous biodegradation of a phenol and 3,4-dimethylphenol mixture under denitrifying conditions.
Toxicity and kinetic parameters of the aerobic biodegradation of the phenol and alkylphenols by a mixed culture.
Biodegradation of dimethylphenols by bacteria with different ring-cleavage pathways of phenolic compounds.
Capture of a labile substrate by expulsion of water molecules from the active site of nicotinate mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase (CobT) from Salmonella enterica.
Derivative spectrophotometry in the analysis of mixtures of phenols and herbicides.
Determination of phenols in soil by supercritical fluid extraction-capillary electrochromatography.
Gas chromatographic-mass spectrometric identification and quantitation of benzyl alcohol in serum after derivatization with perfluorooctanoyl chloride: a new derivative.
Gas chromatographic-mass spectrometric identification and quantitation of benzyl alcohol from human serum and postmortem blood after derivatization with 4-carbethoxy hexafluorobutyryl chloride: a novel derivative.
A novel derivatization of phenol after extraction from human serum using perfluorooctanoyl chloride for gas chromatography-mass spectrometric confirmation and quantification.
Gas chromatographic-mass spectrometric identification and quantitation of urinary phenols after derivatization with 4-carbethoxyhexafluorobutyryl chloride, a novel derivative.
Cloning of the genes for and characterization of the early stages of toluene and o-xylene catabolism in Pseudomonas stutzeri OX1.
Gas chromatographic determination of urinary o-cresol for the monitoring of toluene exposure.
Initial steps in the degradation of 3,4-dimethylbenzoic acid by Pseudomonas putida strain DMB.
Metabolism of phenols by Ochromonas danica.
Formation of Dimethylmuconolactones from Dimethylphenols by Alcaligenes eutrophus JMP 134.
Aromatic effector activation of the NtrC-like transcriptional regulator PhhR limits the catabolic potential of the (methyl)phenol degradative pathway it controls.
An aromatic effector specificity mutant of the transcriptional regulator DmpR overcomes the growth constraints of Pseudomonas sp. strain CF600 on para-substituted methylphenols.
A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1.
Degradation of phenol and phenolic compounds by Pseudomonas putida EKII.
Nucleotide sequence and functional analysis of the complete phenol/3,4-dimethylphenol catabolic pathway of Pseudomonas sp. strain CF600.
Anaerobic degradation of cresols by denitrifying bacteria.
Location and organization of the dimethylphenol catabolic genes of Pseudomonas CF600.
Molecular analysis of a plasmid-encoded phenol hydroxylase from Pseudomonas CF600.
Isolation of a Pseudomonas stutzeri strain that degrades o-xylene.
Biotransformation of nitric oxide, nitrite and nitrate.
Solubility behavior of phenolic compounds in hexane-ethyl acetate, hexane-ethyl myristate, and hexane-ethyl pivalate cosolvent systems.
A modified spectrophotometric methods for nitrate in plants, soils and water by nitration of 3,4-dimethylphenol.

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
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB32151
FooDB:FDB008879
Export Tariff Code:2907.19.8000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 122.16690063477
Melting Point 64 to 68°C @ 760 mm Hg
Vapor Pressure 0.053 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 2.23
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
water, 4668 mg/L @ 25 °C (est) Yes
water, 4760 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Dry
General comment DIMETHYLPHENOL slightly smoky and earthy character provides nice roasted notes to seafood, mushroom and coffee flavors. flat dry
Flavor Type: Smoky
smoky, sweet, earthy, burnt
General comment Smoky, sweet and earthy notes
DIMETHYLPHENOL slightly smoky and earthy character provides nice roasted notes to seafood, mushroom and coffee flavors. Nice smoky, sweet and earthy notes

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 727 mg/kg
(Maazik, 1968)

oral-rabbit LD50 800 mg/kg
(Maazik, 1968)

oral-mouse LD50 400 mg/kg
(Maazik, 1968)

oral-rat LD50 1600 mg/kg
(Eastman Kodak Co., 1991c)

intraperitoneal-mouse LD50 50 mg/kg
SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: ATAXIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
National Technical Information Service. Vol. OTS0533431

oral-mouse LD50 400 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-rabbit LD50 800 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: ATAXIA
Hygiene and Sanitation Vol. 33(7-9), Pg. 329, 1968.

intraperitoneal-rat LD50 200 mg/kg
KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0533431

oral-rat LD50 727 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:
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): 5.70 (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: 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

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
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):95-65-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7249
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2261
WGK Germany:3
3,4-dimethylphenol
Chemidplus:0000095658
EPA/NOAA CAMEO:hazardous materials
RTECS:ZE6300000 for cas# 95-65-8