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4-ethyl phenol

Chemical Structure

General Material Information

Preferred name 4-ethyl phenol
Trivial Name 4-Ethylphenol
Short Description p-ethylphenol
Formula C8 H10 O
CAS Number 123-07-9
Deleted CAS Number 1326305-80-9
FEMA Number 3156
Flavis Number 4.022
ECHA Number 204-598-6
FDA UNII AGG7E6G0ZC
Nikkaji Number J2.496A
Beilstein Number 1363317
MDL MFCD00002393
COE Number 550
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 694 p-ethylphenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 123-07-9 ; P-ETHYLPHENOL
Synonyms
  • benzene,1-ethyl,4-hydroxy
  • p- ethyl phenol
  • para- ethyl phenol
  • 1-ethyl-4-hydroxybenzene
  • 4-ethylphenol
  • p- ethylphenol
  • para- ethylphenol
  • p- ethylphenol (food grade)
  • p- ethylphenol natural
  • 1-hydroxy-4-ethyl benzene
  • 1-hydroxy-4-ethylbenzene
  • 4-hydroxyethyl benzene
  • 4-hydroxyethylbenzene
  • 4-hydroxyphenyl ethane
  • (4-hydroxyphenyl)ethane
  • 4-hydroxyphenylethane
  • phenol, 4-ethyl-
  • phenol, p-ethyl-
  • 4-Ethylphenol
  • p-Ethylphenol
  • 1-Ethyl-4-hydroxybenzene
  • (4-Hydroxyphenyl)ethane
  • (p-Hydroxyphenyl)ethane
  • p-Hydroxyethylbenzene
  • NSC 62012

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

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Literature & References

4-ethylphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:123-07-9
Pubchem (cid):31242
Pubchem (sid):134974380
Flavornet:123-07-9
Pherobase:View
Publications by US Patents
3,946,080 - Flavouring and perfuming ingredients
3,952,024 - Furfurylthioacetone
Publications by PubMed
Occurrence of Brettanomyces/Dekkera in Brazilian red wines and its correlation with ethylphenols.
Osmotic stress response in the wine yeast Dekkera bruxellensis.
Aroma chemistry of African Oryza glaberrima and Oryza sativa rice and their interspecific hybrids.
Comparison of fermented soybean paste (Doenjang) prepared by different methods based on profiling of volatile compounds.
[Identification of volatile organic compounds in the manures of cow, hog and chicken by solid phase microextraction coupled with gas chromatography/mass spectrometry].
Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Key differences in the odor profiles of four high-quality Spanish aged red wines.
A Response Surface Methodology study on the role of factors affecting growth and volatile phenol production by Brettanomyces bruxellensis ISA 2211 in wine.
Microwave-assisted deuterium exchange: the convenient preparation of isotopically labelled analogues for stable isotope dilution analysis of volatile wine phenols.
Sorption of 4-ethylguaiacol and 4-ethylphenol on yeast cell walls, using a synthetic wine.
Aromatic profile of ciders by chemical quantitative, gas chromatography-olfactometry, and sensory analysis.
Volatile constituents of commercial imported and domestic black-ripe table olives (Olea europaea).
Influence of the matrix composition on the volatility and sensory perception of 4-ethylphenol and 4-ethylguaiacol in model wine solutions.
Impact of sulfur dioxide and temperature on culturability and viability of Brettanomyces bruxellensis in Wine.
On-line monitoring of food fermentation processes using electronic noses and electronic tongues: a review.
Metabolism of nonesterified and esterified hydroxycinnamic acids in red wines by Brettanomyces bruxellensis.
Phenolic biotransformations during conversion of ferulic acid to vanillin by lactic acid bacteria.
Osmotic stress response in the wine yeast Dekkera bruxellensis.
Aroma chemistry of African Oryza glaberrima and Oryza sativa rice and their interspecific hybrids.
Biotransformation of rice bran to ferulic acid by pediococcal isolates.
Molecular and physiological comparison of spoilage wine yeasts.
Detection of Brettanomyces spp. in red wines using real-time PCR.
Effect of ethanol on the sorption of four targeted wine volatile compounds in a polyethylene film.
Characterization of the "viable but nonculturable" (VBNC) state in the wine spoilage yeast Brettanomyces.
Hydroxycinnamic acid ethyl esters as precursors to ethylphenols in wine.
Implications of Lactobacillus collinoides and Brettanomyces/Dekkera anomala in phenolic off-flavour defects of ciders.
Screening of representative cider yeasts and bacteria for volatile phenol-production ability.
Comparison of fermented soybean paste (Doenjang) prepared by different methods based on profiling of volatile compounds.
Factors influencing the production of volatile phenols by wine lactic acid bacteria.
Ustilago maydis killer toxin as a new tool for the biocontrol of the wine spoilage yeast Brettanomyces bruxellensis.
Identification and characterization of Dekkera bruxellensis, Candida pararugosa, and Pichia guilliermondii isolated from commercial red wines.
A metabolite profiling approach to identify biomarkers of flavonoid intake in humans.
Influence of the drying processes of yeasts on their volatile phenol sorption capacity in model wine.
Modeling quality of premium spanish red wines from gas chromatography-olfactometry data.
Minimization of ethylphenol precursors in red wines via the formation of pyranoanthocyanins by selected yeasts.
Molecular identification of Brettanomyces bruxellensis strains isolated from red wines and volatile phenol production.
Genetic diversity and physiological traits of Brettanomyces bruxellensis strains isolated from Tuscan Sangiovese wines.
A method for estimating Dekkera/Brettanomyces populations in wines.
Factors affecting the hydroxycinnamate decarboxylase/vinylphenol reductase activity of dekkera/brettanomyces: application for dekkera/brettanomyces control in red wine making.
Ileal and faecal digestibility of daidzein and genistein and plasma bioavailability of these isoflavones and their bioactive metabolites in the ovariectomised rat.
Effects of yeast cell-wall characteristics on 4-ethylphenol sorption capacity in model wine.
Survey of enzyme activity responsible for phenolic off-flavour production by Dekkera and Brettanomyces yeast.
Smoke-derived taint in wine: the release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke.
The effect of sugar concentration and temperature on growth and volatile phenol production by Dekkera bruxellensis in wine.
Partial vinylphenol reductase purification and characterization from Brettanomyces bruxellensis.
Physiological and oenological traits of different Dekkera/Brettanomyces bruxellensis strains under wine-model conditions.
Comparison of metal oxide-based electronic nose and mass spectrometry-based electronic nose for the prediction of red wine spoilage.
Dekkera and Brettanomyces growth and utilisation of hydroxycinnamic acids in synthetic media.
Smoke-derived taint in wine: effect of postharvest smoke exposure of grapes on the chemical composition and sensory characteristics of wine.
4-ethylphenol and 4-ethylguaiacol in wines: estimating non-microbial sourced contributions and toxicological considerations.
Multiple headspace solid-phase microextraction for eliminating matrix effect in the simultaneous determination of haloanisoles and volatile phenols in wines.
Determination of 4-ethylphenol and 4-ethylguaiacol in wines by LC-MS-MS and HPLC-DAD-fluorescence.
Phyto- and endogenous estrogens differently activate intracellular calcium ion mobilization in bovine endometrial cells.
An accurate and reproducible method for the quantitative analysis of isoflavones and their metabolites in rat plasma using liquid chromatography/mass spectrometry combined with photodiode array detection.
Sorption behavior of volatile phenols at the oak wood/wine interface in a model system.
Equol and para-ethyl-phenol stimulate prostaglandin F(2alpha) secretion in bovine corpus luteum: intracellular mechanisms of action.
Development of an enrichment medium to detect Dekkera/Brettanomyces bruxellensis, a spoilage wine yeast, on the surface of grape berries.
Phytoestrogens and their metabolites inhibit the sensitivity of the bovine corpus luteum to luteotropic factors.
Molecular typing of the yeast species Dekkera bruxellensis and Pichia guilliermondii recovered from wine related sources.
Main compounds responsible for off-odour of strawberries infected by Phytophthora cactorum.
Enrichment of cheeses manufactured from cow's and sheep's milk blends with sheep-like species-related alkylphenols.
Phenolic compounds in olive oils intended for refining: formation of 4-ethylphenol during olive paste storage.
Distribution of conjugates of alkylphenols in milk from different ruminant species.
The effects of sample preparation and gas chromatograph injection techniques on the accuracy of measuring guaiacol, 4-methylguaiacol and other volatile oak compounds in oak extracts by stable isotope dilution analyses.
Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium quality spanish aged red wines.
Volatile compounds in a spanish red wine aged in barrels made of Spanish, French, and American oak wood.
Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Key differences in the odor profiles of four high-quality Spanish aged red wines.
Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions.
Evaluation of Smoky Taste in Cocoa Powder.
Decarboxylation of substituted cinnamic acids by lactic acid bacteria isolated during malt whisky fermentation.

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
Metabolomics Database:Search
KEGG (GenomeNet):C13637
HMDB (The Human Metabolome Database):HMDB29306
FooDB:FDB000358
Export Tariff Code:2907.19.2000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Formulations/Preparations:
the purity of the commercial product is 98%.

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 122.16690063477
Melting Point 44 to 46°C @ 760 mm Hg
Boiling Point 218 to 219°C @ 760 mm Hg
Vapor Pressure 0.083 mmHg @ 25 °C
Vapor Density 4.2
Flash Point TCC Value 100.56 °C TCC
logP (o/w) 2.58
Solubility
water, 2346 mg/L @ 25 °C (est) Yes
water, 4900 mg/L @ 25 °C (exp) Yes

Organoleptic Properties

Odor Type: Smoky
phenolic, castoreum, smoky, guaiacol, savory
Odor strength high , recommend smelling in a 1.00 % solution or less
Substantivity 109 hour(s) at 100.00 %
Luebke, William tgsc, (2006) At 1.00 % in dipropylene glycol. phenolic castoreum smoke guaiacol
Mosciano, Gerard P&F 23, No. 3, 55, (1998) At 1.00 %. Smoke, phenolic, creosote and savory
Flavor Type: Smoky
phenolic, smoky, bacon, ham
Mosciano, Gerard P&F 23, No. 3, 55, (1998) At 2.50 ppm. Phenolic, smoke, bacon and ham

Occurrences

Potential Uses

Applications
Odor purposes Castoreum
Flavoring purposes Bacon, Coffee, Cranberry, Rum
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
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 - Wear suitable protective clothing.
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 > 5000 mg/kg
(Blaszcak & Auletta, 1986)

intraperitoneal-mouse LD50 138 mg/kg
Journal of Medicinal Chemistry. Vol. 18, Pg. 868, 1975.

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
Recommendation for 4-ethyl phenol usage levels up to:
0.0500 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 3.50 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.10 (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: -0.20000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: -0.20000
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
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):123-07-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :31242
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2430
WGK Germany:3
4-ethylphenol
Chemidplus:0000123079
RTECS:SL4040000 for cas# 123-07-9