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para-cresol

Chemical Structure

General Material Information

Preferred name para-cresol
Trivial Name p-Cresol
Short Description 4-hydroxytoluene
Formula C7 H8 O
CAS Number 106-44-5
FEMA Number 2337
Flavis Number 4.028
ECHA Number 203-398-6
FDA UNII 1MXY2UM8NV
Nikkaji Number J1.185A
Beilstein Number 1305151
MDL MFCD00002376
COE Number 619
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 693 p-cresol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 106-44-5 ; P-CRESOL
Synonyms
  • 1-hydroxy-4-methyl benzene
  • 1-hydroxy-4-methylbenzene
  • 1-Hydroxy-4-methylbenzene
  • 1-methyl-4-hydroxybenzene
  • 1-Methyl-4-hydroxybenzene
  • 4-cresol
  • 4-Cresol
  • 4-hydroxytoluene
  • 4-Hydroxytoluene
  • 4-methyl phenol
  • 4-methylphenol
  • cresol para pure
  • NSC 3696
  • p- methylphenol
  • p-cresol
  • p-Cresol
  • p-cresol natural
  • p-Cresylic acid
  • p-cresylic acid
  • p-hydroxytoluene
  • p-Hydroxytoluene
  • p-methyl hydroxybenzene
  • p-methyl phenol
  • p-Methylhydroxybenzene
  • p-Methylphenol
  • p-oxy toluene
  • p-Oxytoluene
  • p-Toluol
  • p-toluol
  • p-Tolyl alcohol
  • para-cresylic acid
  • para-hydroxytoluene
  • para-methyl hydroxybenzene
  • para-methyl phenol
  • para-oxy toluene
  • para-toluol
  • paracresol
  • Phenol, 4-methyl-

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

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Literature & References

4-methylphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:106-44-5
Pubchem (cid):2879
Pubchem (sid):134971768
Flavornet:106-44-5
Pherobase:View
Publications by PubMed
Determination of the importance of in-mouth release of volatile phenol glycoconjugates to the flavor of smoke-tainted wines.
Effect of ubiquinol-10 on citral stability and off-flavor formation in oil-in-water (O/W) nanoemulsions.
Contribution of several volatile phenols and their glycoconjugates to smoke-related sensory properties of red wine.
Mechanisms of flavor release in chewing gum: cinnamaldehyde.
Aroma components of American country ham.
Characterization of odorants causing an atypical aroma in white pepper powder (Piper nigrum L.) based on quantitative measurements and orthonasal breakthrough thresholds.
Aroma compounds in sweet whey powder.
Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin.
Characteristic aroma components of rennet casein.
Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey.
Volatile flavor components of stored nonfat dry milk.
Characteristic aroma components of British Farmhouse Cheddar cheese.
Cloud-point extraction and reversed-phase high performance liquid chromatography for analysis of phenolic compounds and their antioxidant activity in Thai local wines.
Determination of the importance of in-mouth release of volatile phenol glycoconjugates to the flavor of smoke-tainted wines.
Metabonomic analysis of quercetin against the toxicity of chronic exposure to low-level dichlorvos in rats via ultra-performance liquid chromatography-mass spectrometry.
A new method for preconcentration and determination of mercury in fish, shellfish and saliva by cold vapour atomic absorption spectrometry.
Effect of uremic serum and uremic toxins on drug metabolism in human microsomes.
Effect of ubiquinol-10 on citral stability and off-flavor formation in oil-in-water (O/W) nanoemulsions.
Identification of volatile compounds from a food-grade vinegar attractive to house flies (Diptera: Muscidae).
Microbial-mammalian cometabolites dominate the age-associated urinary metabolic phenotype in Taiwanese and American populations.
Metabolic profiling of the impact of oligofructose-enriched inulin in Crohn's disease patients: a double-blinded randomized controlled trial.
Modulation of protein fermentation does not affect fecal water toxicity: a randomized cross-over study in healthy subjects.
Ovariectomized mouse uterotrophic assay of 36 chemicals.
Effects of potato fiber and potato-resistant starch on biomarkers of colonic health in rats fed diets containing red meat.
Effects of corn processing method and dietary inclusion of corn wet distillers grains with solubles on odor and gas production in cattle manure.
The production of p-cresol sulfate and indoxyl sulfate in vegetarians versus omnivores.
Rapid discrimination and characterization of vanilla bean extracts by attenuated total reflection infrared spectroscopy and selected ion flow tube mass spectrometry.
Impact of short-term intake of red wine and grape polyphenol extract on the human metabolome.
Contribution of several volatile phenols and their glycoconjugates to smoke-related sensory properties of red wine.
Consumption of breads containing in situ-produced arabinoxylan oligosaccharides alters gastrointestinal effects in healthy volunteers.
Relevance of protein fermentation to gut health.
An arabinoxylan-rich fraction from wheat enhances caecal fermentation and protects colonocyte DNA against diet-induced damage in pigs.
Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics.
Functional analysis of colonic bacterial metabolism: relevant to health?
Effects of frozen storage and vacuum packaging on free fatty acid and volatile composition of Turkish Motal cheese.
Carrion mimicry in a South African orchid: flowers attract a narrow subset of the fly assemblage on animal carcasses.
High-protein/high red meat and high-carbohydrate weight-loss diets do not differ in their effect on faecal water genotoxicity tested by use of the WIL2-NS cell line and with other biomarkers of bowel health.
p-Cresol and cardiovascular risk in mild-to-moderate kidney disease.
Radical-scavenging activity and cytotoxicity of p-methoxyphenol and p-cresol dimers.
Interaction of phenol, o-cresol, and p-cresol with a clay-rich soil sample.
Tolerance of arabinoxylan-oligosaccharides and their prebiotic activity in healthy subjects: a randomised, placebo-controlled cross-over study.
Characterization of aroma-active compounds, sensory properties, and proteolysis in Ezine cheese.
Radiation metabolomics. 3. Biomarker discovery in the urine of gamma-irradiated rats using a simplified metabolomics protocol of gas chromatography-mass spectrometry combined with random forests machine learning algorithm.
p-Cresol inhibits IL-12 production by murine macrophages stimulated with bacterial immunostimulant.
Dose-response effect of arabinoxylooligosaccharides on gastrointestinal motility and on colonic bacterial metabolism in healthy volunteers.
Measurement of phenol and p-cresol in urine and feces using vacuum microdistillation and high-performance liquid chromatography.
Composition and antifungal activity of the essential oil of the Brazilian Chenopodium ambrosioides L.
Aroma components of American country ham.
Wholegrain foods made from a novel high-amylose barley variety (Himalaya 292) improve indices of bowel health in human subjects.
Fasting enhances p-Cresol production in the rat intestinal tract.
Aclacinomycin oxidoreductase (AknOx) from the biosynthetic pathway of the antibiotic aclacinomycin is an unusual flavoenzyme with a dual active site.
Uptake and localization of gaseous phenol and p-cresol in plant leaves.
The chemical nature of fetid floral odours in stapeliads (Apocynaceae-Asclepiadoideae-Ceropegieae).
Influence of phenol, p-cresol and indole on growth and survival of intestinal lactic acid bacteria.
Potent inhibitory effects of black tea theaflavins on off-odor formation from citral.
Multidimensional gas chromatography-olfactometry for the identification and prioritization of malodors from confined animal feeding operations.
Characterization of odorants causing an atypical aroma in white pepper powder (Piper nigrum L.) based on quantitative measurements and orthonasal breakthrough thresholds.
The unbearable lightness of "light" cigarettes: a comparison of smoke yields in six varieties of Canadian "light" cigarettes.
Enrichment of cheeses manufactured from cow's and sheep's milk blends with sheep-like species-related alkylphenols.
A kinetic study of p-cresol oxidation by quince fruit polyphenol oxidase.
Aroma compounds in sweet whey powder.
Characteristic aroma components of rennet casein.
In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.
Whole-grain rye and wheat foods and markers of bowel health in overweight middle-aged men.
Sequestering ability of butylated hydroxytoluene, propyl gallate, resveratrol, and vitamins C and E against ABTS, DPPH, and hydroxyl free radicals in chemical and biological systems.
Identification and quantification of aroma-active components that contribute to the distinct malty flavor of buckwheat honey.
Volatile flavor components of stored nonfat dry milk.
Two OPEEs (organic phase enzyme electrodes) used to check the percentage water content in hydrophobic foods and drugs.
Characteristic aroma components of British Farmhouse Cheddar cheese.
Proteolytic activation of latent Paraguaya peach PPO. Characterization of monophenolase activity.
Vegan diet in physiological health promotion.
Nitrosation of phenolic compounds: inhibition and enhancement.
Micellar electrokinetic chromatography with bis(2-ethylhexyl)sodium sulfosuccinate vesicles determination of synthetic food antioxidants.
Attenuation of luminol-amplified chemiluminescent intensity and lipid peroxidation in the livers of quercetin-fed mice.
Influence of dietary protein supplements on the formation of bacterial metabolites in the colon.
Effect of tea polyphenols on fecal flora and fecal metabolic products of pigs.
Effects of eating an uncooked vegetable diet for 1 week.
Effect of Konjac mannan on intestinal microbial metabolism in mice bearing human flora and in conventional F344 rats.
Determination of phenol in poly(vinyl chloride).
Hydroxyurea and p-aminophenol are the suicide inhibitors of ascorbate peroxidase.
[Determination of butylated hydroxy-anisole in oily foods by high-performance liquid chromatography with fluorescence detection].
Capillary GC analysis of compounds leached into parenteral solutions packaged in plastic bags.
Effects of t-butyl-4-hydroxyanisole and other phenolic antioxidants on tumoral cells and Trypanosoma parasites.
Gas chromatographic, liquid chromatographic, and titrimetric procedures for determination of glycerin in allergenic extracts and diagnostic antigens: comparative study.
Effects of BHA and related phenols on the forestomach of rats.
Dependence of curing time, peak temperature, and mechanical properties on the composition of bone cement.
The urinary excretion of bacterial amino-acid metabolites by rats fed saccharin in the diet.
Effects of zeolite a or clinoptilolite in diets of growing swine.
Pharmacologic and genetic studies on the modulatory effects of butylated hydroxytoluene on mouse lung adenoma formation.
Modulation of azaserine-induced pancreatic foci by phenolic antioxidants in rats.
The origin of urinary aromatic compounds excreted by ruminants. 4. The potential use of urine aromatic acid and phenol outputs as a measure of voluntary food intake.
A study of the rates of the competitive nitrosations of pyrrolidine, p-cresol and L-cysteine hydrochloride.
The fate of 2,6-bis-(1'-methyl-14C-heptadecyl)-p-cresol(Dioctadecyl-p-cresol-14C) in the rat.
Studies of the physiological effects of 2,6-bis-(1'-methylheptadecyl)-p-cresol (Dioctadecyl-p-cresol) in the rat and dog.

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
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C01468
HMDB (The Human Metabolome Database):HMDB01858
FooDB:FDB008789
Export Tariff Code:2907.12.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•grades: technical: 98%, 99.0% minimum purity ... •pure cresol is a mixture of ortho-, meta- & para-isomers. crude cresol (commercial cresol) is a mixture of aromatic cmpd containing about 20% of o-cresol, 40% of m-cresol, & 30% of p-cresol with small amt of phenol & xylenols. •generally, m- and p- isomers are used industrially as a mixture containing 40% to 65% m-cresol.

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 108.13996124268
Melting Point 32 to 35°C @ 760 mm Hg
Boiling Point 201.8 to 202°C @ 760 mm Hg
Boiling Point 121 to 122°C @ 50 mm Hg
Vapor Pressure 0.11 mmHg @ 25 °C
Vapor Density 3.72
Flash Point TCC Value 89.44 °C TCC
logP (o/w) 1.94
Solubility
alcohol Yes
water, 2.15E+04 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Phenolic
phenolic, narcissus, animal, mimosa
Odor strength high , recommend smelling in a 0.10 % solution or less
Substantivity 400 hour(s) at 10.00 % in dipropylene glycol
Luebke, William tgsc, (1981) At 0.10 % in dipropylene glycol. phenolic narcissus animal mimosa
Scentspiracy Adding animalic nuance to floral intensity
Flavor Type: Phenolic
phenolic
General comment Phenolic

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
T - Toxic.
R 24/25 - Toxic in contact with skin and if swallowed.
R 34 - Causes burns.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
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.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 3), H301
Acute toxicity, Dermal (Category 3), H311
Skin corrosion (Category 1B), H314
Acute aquatic toxicity (Category 2), H401
Chronic aquatic toxicity (Category 2), H411
GHS Label elements, including precautionary statements
Pictogramcorrosion.jpgskull.jpg
Signal word Danger
Hazard statement(s)
H301 - Toxic if swallowed
H311 - Toxic in contact with skin
H314 - Causes severe skin burns and eye damage
H401 - Toxic to aquatic life
H411 - Toxic to aquatic life with long lasting effects
Precautionary statement(s)
P260 - Do not breathe dust/fume/gas/mist/vapours/spray.
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P273 - Avoid release to the environment.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P301 + P310 - IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P330 + P331 - IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303 + P361 + P353 - IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P310 - Immediately call a POISON CENTER or doctor/physician.
P361 - Remove/Take off immediately all contaminated clothing.
P363 - Wash contaminated clothing before reuse.
P391 - Collect spillage. Hazardous to the aquatic environment
P405 - Store locked up.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Human Experience:
4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 207 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 5-5/1969

oral-mouse LD50 344 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 58, 1974.

intraperitoneal-mouse LD50 25 mg/kg
"Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 58, 1959.

unreported-mouse LD50 160 mg/kg
British Journal of Cancer. Vol. 6, Pg. 160, 1952.

oral-rabbit LDLo 620 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.

unreported-rat LD50 1440 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.

intravenous-rabbit LDLo 180 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.

Dermal Toxicity:
skin-rabbit LD50 301 mg/kg
BEHAVIORAL: TREMOR KIDNEY, URETER, AND BLADDER: OTHER CHANGES GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 5-5/1969

skin-rat LD50 750 mg/kg
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 58, 1974.

subcutaneous-cat LDLo 80 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.

subcutaneous-mouse LDLo 150 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1361, 1935.

subcutaneous-rabbit LDLo 300 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1361, 1935.

subcutaneous-rat LDLo 500 mg/kg
"Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 58, 1959.

subcutaneous-frog LDLo 150 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1361, 1935.

subcutaneous-guinea pig LDLo 200 mg/kg
"Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 58, 1959.

Inhalation Toxicity:
inhalation-rat LC50 > 710 mg/m3/1H
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 5-5/1969

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 para-cresol usage levels up to:
0.0500 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.97 (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: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 0.010002.00000
beverages(nonalcoholic): -0.67000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 0.010001.00000
fruit ices: 0.010001.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 0.010002.00000
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
NIOSH International Chemical Safety Cards:search
NIOSH Pocket Guide:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):106-44-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :2879
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 3455
WGK Germany:2
4-methylphenol
Chemidplus:0000106445
EPA/NOAA CAMEO:hazardous materials
RTECS:106-44-5