We have found 46587 results matching your criteria.
Please wait while we search...
  1. 1.
    General Material Information
  2. 2.
    PhysChem Properties
  3. 3.
    Occurrences
  4. 4.
    Organoleptic Properties
  5. 5.
    Suppliers
  6. 6.
    Potential Uses
  7. 7.
    Regulatory & Documentation
  8. 8.
    Safety Information
  9. 9.
    Other Information
  10. 10.
    Blenders & Components
  11. 11.
    Literature & References

4-ethyl guaiacol

Chemical Structure

General Material Information

Preferred name 4-ethyl guaiacol
Trivial Name 4-Ethylguaiacol
Short Description 4-ethylguaiacol
Formula C9 H12 O2
CAS Number 2785-89-9
FEMA Number 2436
Flavis Number 4.008
ECHA Number 220-500-4
FDA UNII C9NFD83BJ5
Nikkaji Number J141.497F
MDL MFCD00038714
COE Number 176
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 716 4-ethylguaiacol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 2785-89-9 ; 4-ETHYLGUAIACOL
Synonyms
  • homo creosol
  • nat.4-ethyl guaiacol
  • p- ethyl guaiacol
  • para- ethyl guaiacol
  • 4-ethyl guaiacol FCC
  • 4-ethyl guaiacol natural
  • 4-ethyl guaiacol synthetic
  • 4-ethyl-2-methoxyphenol
  • ethyl-4 guaiacol
  • 4-ethylguaiacol
  • p- ethylguaiacol
  • para- ethylguaiacol
  • guaiacol, 4-ethyl-
  • guaiacyl ethane
  • guaiacylethane
  • 1-hydroxy-2-methoxy-4-ethyl benzene
  • 1-hydroxy-2-methoxy-4-ethylbenzene
  • 4-hydroxy-3-methoxy ethylbenzene
  • 4-hydroxy-3-methoxyethyl benzene
  • 4-hydroxy-3-methoxyphenyl ethane
  • 4-hydroxy-3-methoxyphenylethane
  • 2-methoxy-4-ethyl phenol
  • 2-methoxy-4-ethylphenol
  • phenol, 4-ethyl-2-methoxy-
  • 4-ethyl-2-methoxyphenol
  • p-Ethylguaiacol
  • 4-Ethylguaiacol
  • 4-Hydroxy-3-methoxyethylbenzene
  • 2-Methoxy-4-ethylphenol
  • 4-Hydroxy-3-methoxyphenylethane
  • NSC 82313

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

Google Scholar Start search
Google Books Start search
Google Patents Start search
Perfumer & Flavorists Start search
EU Patents Start search
PubMeb Start search
NCBI Start search

Literature & References

4-ethyl-2-methoxyphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:2785-89-9
Pubchem (cid):62465
Pubchem (sid):135019447
Flavornet:2785-89-9
Pherobase:View
Publications by US Patents
3,946,080 - Flavouring and perfuming ingredients
3,952,024 - Furfurylthioacetone
Publications by PubMed
The binding of 4-ethylguaiacol with polyaniline-based materials in wines.
Volatile fingerprint of Brazilian defective coffee seeds: corroboration of potential marker compounds and identification of new low quality indicators.
Characterisation of volatile compounds in a smoke flavouring from rice husk.
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.
Influence of the matrix composition on the volatility and sensory perception of 4-ethylphenol and 4-ethylguaiacol in model wine solutions.
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.
Occurrence of Brettanomyces/Dekkera in Brazilian red wines and its correlation with ethylphenols.
Evaluation of aroma differences between high-salt liquid-state fermentation and low-salt solid-state fermentation soy sauces from China.
Selective defunctionalization by TiO2 of monomeric phenolics from lignin pyrolysis into simple phenols.
Osmotic stress response in the wine yeast Dekkera bruxellensis.
Impact of Australian Dekkera bruxellensis strains grown under oxygen-limited conditions on model wine composition and aroma.
Studies on the key aroma compounds in raw (unheated) and heated Japanese soy sauce.
New application of the QuEChERS methodology for the determination of volatile phenols in beverages by liquid chromatography.
Bioprocess design for the microbial production of natural phenolic compounds by Debaryomyces hansenii.
Detection of Brettanomyces spp. in red wines using real-time PCR.
Prenatal and early sucking influences on dietary preference in newborn, weaning, and young adult cats.
Genome shuffling of Hansenula anomala to improve flavour formation of soy sauce.
Selective production of 4-ethylphenolics from lignin via mild hydrogenolysis.
Optimisation of a sensitive method based on ultrasound-assisted emulsification-microextraction for the simultaneous determination of haloanisoles and volatile phenols in wine.
Comparison of key aroma compounds in five different types of Japanese soy sauces by aroma extract dilution analysis (AEDA).
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.
Ultrasound-assisted emulsification-microextraction for the sensitive determination of Brett character responsible compounds in wines.
Identification and thermochemical analysis of high-lignin feedstocks for biofuel and biochemical production.
Comparison of fermented soybean paste (Doenjang) prepared by different methods based on profiling of volatile compounds.
Development of a dispersive liquid-liquid microextraction method for the simultaneous determination of the main compounds causing cork taint and Brett character in wines using gas chromatography-tandem mass spectrometry.
Interaction Mechanisms between guaiacols and lignin: the conjugated double bond makes the difference.
Sorptive extraction with in-sample acetylation for gas chromatography-mass spectrometry determination of ethylphenol species in wine samples.
Optimisation of a simple and reliable method based on headspace solid-phase microextraction for the determination of volatile phenols in beer.
Use of microfungi in the treatment of oak chips: possible effects on wine.
Effect of halotolerant starter microorganisms on chemical characteristics of fermented chum salmon (Oncorhynchus keta) sauce.
Genome shuffling of Zygosaccharomyces rouxii to accelerate and enhance the flavour formation of soy sauce.
Inhibition by 2-methoxy-4-ethylphenol of Ca2+ influx through acquired and native N-methyl-D-aspartate-receptor channels.
Headspace solid-phase microextraction for direct determination of volatile phenols in cider.
Production of 4-ethylphenol from 4-hydroxycinnamic acid by Lactobacillus sp. isolated from a swine waste lagoon.
Identification and characterization of Dekkera bruxellensis, Candida pararugosa, and Pichia guilliermondii isolated from commercial red wines.
Spoilage yeasts in Patagonian winemaking: molecular and physiological features of Pichia guilliermondii indigenous isolates.
Chemical causes of the typical burnt smell after accidental fires.
Volatile composition of Merlot wine from different vine water status.
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.
Comparison of two SPME fibers for the extraction of some off-flavor cork-taint compounds in bottled wines investigated by GC-HRMS.
Prediction of sensory properties of Brazilian Arabica roasted coffees by headspace solid phase microextraction-gas chromatography and partial least squares.
Effects of elevated CO2 on grapevine (Vitis vinifera L.): volatile composition, phenolic content, and in vitro antioxidant activity of red wine.
Relationships between sensory descriptors, consumer acceptability and volatile flavor compounds of American dry-cured ham.
Smoke-derived taint in wine: the release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke.
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.
The chemical characterization of the aroma of dessert and sparkling white wines (Pedro Ximénez, Fino, Sauternes, and Cava) by gas chromatography-olfactometry and chemical quantitative analysis.
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.
Quantitative determination of 4-ethylphenol and 4-ethyl-2-methoxyphenol in wines by a stable isotope dilution assay.
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.
The reactivity of ortho-methoxy-substituted catechol radicals with sulfhydryl groups: contribution for the comprehension of the mechanism of inhibition of NADPH oxidase by apocynin.
Determination of volatile phenols in red wines by dispersive liquid-liquid microextraction and gas chromatography-mass spectrometry detection.
Cytoprotective properties of phenolic antidiarrheic ingredients in cultured astrocytes and neurons of rat brains.
Bioconversion of ferulic acid to 4-vinylguaiacol and 4-ethylguaiacol and of 4-vinylguaiacol to 4-ethylguaiacol by halotolerant yeasts belonging to the genus Candida.
Discovery of a eugenol oxidase from Rhodococcus sp. strain RHA1.
A 4-alkyl-substituted analogue of guaiacol shows greater repellency to savannah tsetse (Glossina spp.).
Determination of volatile phenols in wine using high-performance liquid chromatography with a coulometric array detector.
Characterization of aroma compounds in apple cider using solvent-assisted flavor evaporation and headspace solid-phase microextraction.
Determination of ethylphenols in wine by in situ derivatisation and headspace solid-phase microextraction-gas chromatography-mass spectrometry.
Determination of Brett character responsible compounds in wines by using multiple headspace solid-phase microextraction.
Rapid headspace solid-phase microextraction/gas chromatographic/mass spectrometric assay for the quantitative determination of some of the main odorants causing off-flavours in wine.
Physicochemical model to interpret the kinetics of aroma extraction during wine aging in wood. Model limitations suggest the necessary existence of biochemical processes.
Development of an enrichment medium to detect Dekkera/Brettanomyces bruxellensis, a spoilage wine yeast, on the surface of grape berries.
Synthesis and cosmetic whitening effect of glycosides derived from several phenylpropanoids.
Characterization of cachaça and rum aroma.
Flavor characteristics of lapsang souchong and smoked lapsang souchong, a special Chinese black tea with pine smoking process.
Main compounds responsible for off-odour of strawberries infected by Phytophthora cactorum.
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.
Fungal laccase-catalyzed degradation of hydroxy polychlorinated biphenyls.
Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium quality spanish aged red wines.
Characterization of odor-active compounds in Californian chardonnay wines using GC-olfactometry and GC-mass spectrometry.
Wood creosote, the principal active ingredient of seirogan, an herbal antidiarrheal medicine: a single-dose, dose-escalation safety and pharmacokinetic study.
Extraction and formation dynamic of oak-related volatile compounds from different volume barrels to wine and their behavior during bottle storage.
Determination of 4-ethylguaiacol and 4-ethylphenol in red wines using headspace-solid-phase microextraction-gas chromatography.
Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions.
Immobilized salt-tolerant yeasts: application of a new polyethylene-oxide support in a continuous stirred-tank reactor for flavour production.
Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins.
Measurement of urinary methoxyphenols and their use for biological monitoring of wood smoke exposure.
Solid-phase microextraction method development for headspace analysis of volatile flavor compounds.
Interactions between anthocyanins and aroma substances in a model system. Effect on the flavor of grape-derived beverages.
Quantitative analysis of 4-ethylphenol and 4-ethylguaiacol in red wine.
Potent odorants of raw Arabica coffee. Their changes during roasting.
[Anti-dermaptophyte activity of phenolic compounds in "mokusaku-eki"].
Suppression of intestinal smooth muscle contraction by 4-ethylguaiacol, a constituent of wood creosote.
2-Methylthiazolidine and 4-ethylguaiacol, male sex pheromone components of the cockroachNauphoeta cinerea (dictyoptera, blaberidae): A reinvestigation.
Suppression of intestinal smooth muscle contraction by phenolic compounds.
Analysis of beechwood creosote by gas chromatography-mass spectrometry and high-performance liquid chromatography.

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):HMDB40175
FooDB:FDB019887
YMDB (Yeast Metabolome Database):YMDB01615
Export Tariff Code:2909.50.2000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 152.19303894043
Specific gravity @ 25 °C
Pounds per Gallon 8.829 to 8.854
Refractive Index 1.525 to 1.53 @ 20 °C
Melting Point 13 to 15°C @ 760 mm Hg
Boiling Point 235 to 236°C @ 760 mm Hg
Boiling Point 82 to 85°C @ 1.3 mm Hg
Acid Value 1 max KOH/g
Vapor Pressure 0.017 mmHg @ 25 °C
Vapor Density 5.2
Flash Point TCC Value 107.78 °C TCC
logP (o/w) 2.434 est
Solubility
alcohol Yes
dipropylene glycol Yes
water, 693.8 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Spicy
spicy, smoky, bacon, phenolic, clove, medicinal, woody, sweet, vanilla
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 304 hour(s) at 100.00 %
Luebke, William tgsc, (1996) At 10.00 % in dipropylene glycol. spicy smoky bacon phenolic clove
Mosciano, Gerard P&F 15, No. 1, 19, (1990) Spicy and clove-like with medicinal, woody and sweet vanilla nuances
Flavor Type: Woody
woody, smoky, spicy, sweet, vanilla
Mosciano, Gerard P&F 15, No. 1, 19, (1990) At 30.00 ppm. Woody, smokey and spicy with a sweet vanilla background
Used as a background note in NI flavors (e.g., Cinnamon, Coffee, Cranberry, Rum, Tea, Whisky). Also used in Artificial Smoke flavours, and as a modifier in meat, spice, vanilla and tobacco flavors. Normal use levels in finished consumer product: 0.001-1 ppm. Council of Europe limits: Foods (1 ppm); Beverages (0.1 ppm). Spicy with a sweet vanilla background at 30 ppm.
4-ETHYLGUAIACOL has a typical smoky and clove-like profile complemented by interesting woody and sweet vanilla nuances which are excellent for sweet and meat flavors. Nice smoky, spicy and clove-like notes

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
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:
Not determined
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 guaiacol usage levels up to:
1.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 6.90 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.40 (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: --
beverages(nonalcoholic): -0.05000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -1.10000
fruit ices: -1.10000
gelatins / puddings: -0.23000
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 Substance Registry Services (TSCA):2785-89-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :62465
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
4-ethyl-2-methoxyphenol
Chemidplus:0002785899