4-ethyl guaiacol

4-ethylguaiacol

CAS: 2785-89-9 C9 H12 O2 MW: 152.19304000 spicy woody

Identification

Name4-ethyl guaiacol
IUPAC4-ethyl-2-methoxyphenol
CAS Number2785-89-9
EINECS220-500-4
FDA UNIIC9NFD83BJ5
Molecular FormulaC9 H12 O2
Molecular Weight152.19304000
MDL NumberMFCD00038714
Nikkaji NumberJ141.497F
CoE Number176

Regulatory

JECFA Food Flavoring716 4-ethylguaiacol
DG SANTE Food Flavourings04.008 4-ethylguaiacol
FEMA Number2436
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)2785-89-9 ; 4-ETHYLGUAIACOL
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

Physical Properties

Appearance colorless to pale yellow clear liquid (est)
Assay 98.00 to 100.00
Food Chemicals Codex Listed Yes
Specific Gravity 1.06100 to 1.06400 @ 25.00 °C.
Pounds per Gallon - (est). 8.829 to 8.854
Refractive Index 1.52500 to 1.53000 @ 20.00 °C.
Melting Point 13.00 to 15.00 °C. @ 760.00 mm Hg
Boiling Point 235.00 to 236.00 °C. @ 760.00 mm Hg, 82.00 to 85.00 °C. @ 1.30 mm Hg
Acid Value 1.00 max. KOH/g
Vapor Pressure 0.017000 mmHg @ 25.00 °C. (est)
Vapor Density 5.2 ( Air = 1 )
Flash Point 226.00 °F. TCC ( 107.78 °C. )
logP (o/w) 2.434 (est)
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength medium ,
Substantivity 304 hour(s) at 100.00 %
Odor Description
at 10.00 % in dipropylene glycol.
Spicy and clove-like with medicinal, woody and sweet vanilla nuances
spicy and clove-like with medicinal, woody and sweet vanilla nuances
Odor sample from Sigma-Aldrich
Taste Description
at 30.00 ppm.
spicy with a sweet vanilla background at 30 ppm.
Nice smoky, spicy and clove-like notes

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for 4-ethyl guaiacol usage levels up to1.0000 % 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)
baked goods-
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-
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-

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Potential Uses

FL bacon FR berry FR carnation FR cinnamon FR clove FR coffee FR cranberry FL dairy FR fruit FL meat smoked meat FR peru balsam FR pizza FL rum FL salmon smoked salmon FL smoke FR spice FL tea FR tobacco FR tolu balsam FL tomato FR vanilla FL vegetable FL whiskey

Natural Occurrence

beer PMC brandy grape brandy PMC cassia plant cinnamon PMC coffee arabica coffee bean corn seed malt PMC pepper bell pepper fruit rum PMC sesame seed soy sauce PMC tea leaf tomato whiskey wine

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- US Patents: 3,946,080 - Flavouring and perfuming ingredients PubMed: The binding of 4-ethylguaiacol with polyaniline-based materials in wines. US Patents: 3,952,024 - Furfurylthioacetone PubMed: Volatile fingerprint of Brazilian defective coffee seeds: corroboration of potential marker compounds and identification of new low quality indicators. PubMed: Characterisation of volatile compounds in a smoke flavouring from rice husk. PubMed: Sorption of 4-ethylguaiacol and 4-ethylphenol on yeast cell walls, using a synthetic wine. PubMed: Aromatic profile of ciders by chemical quantitative, gas chromatography-olfactometry, and sensory analysis. PubMed: Influence of the matrix composition on the volatility and sensory perception of 4-ethylphenol and 4-ethylguaiacol in model wine solutions. PubMed: On-line monitoring of food fermentation processes using electronic noses and electronic tongues: a review. PubMed: Metabolism of nonesterified and esterified hydroxycinnamic acids in red wines by Brettanomyces bruxellensis. PubMed: Occurrence of Brettanomyces/Dekkera in Brazilian red wines and its correlation with ethylphenols. PubMed: Evaluation of aroma differences between high-salt liquid-state fermentation and low-salt solid-state fermentation soy sauces from China. PubMed: Selective defunctionalization by TiO2 of monomeric phenolics from lignin pyrolysis into simple phenols. PubMed: Osmotic stress response in the wine yeast Dekkera bruxellensis. PubMed: Impact of Australian Dekkera bruxellensis strains grown under oxygen-limited conditions on model wine composition and aroma. PubMed: Studies on the key aroma compounds in raw (unheated) and heated Japanese soy sauce. PubMed: New application of the QuEChERS methodology for the determination of volatile phenols in beverages by liquid chromatography. PubMed: Bioprocess design for the microbial production of natural phenolic compounds by Debaryomyces hansenii. PubMed: Detection of Brettanomyces spp. in red wines using real-time PCR. PubMed: Prenatal and early sucking influences on dietary preference in newborn, weaning, and young adult cats. PubMed: Genome shuffling of Hansenula anomala to improve flavour formation of soy sauce. PubMed: Selective production of 4-ethylphenolics from lignin via mild hydrogenolysis. PubMed: Optimisation of a sensitive method based on ultrasound-assisted emulsification-microextraction for the simultaneous determination of haloanisoles and volatile phenols in wine. PubMed: Comparison of key aroma compounds in five different types of Japanese soy sauces by aroma extract dilution analysis (AEDA). PubMed: Characterization of the "viable but nonculturable" (VBNC) state in the wine spoilage yeast Brettanomyces. PubMed: Hydroxycinnamic acid ethyl esters as precursors to ethylphenols in wine. PubMed: Implications of Lactobacillus collinoides and Brettanomyces/Dekkera anomala in phenolic off-flavour defects of ciders. PubMed: Ultrasound-assisted emulsification-microextraction for the sensitive determination of Brett character responsible compounds in wines. PubMed: Identification and thermochemical analysis of high-lignin feedstocks for biofuel and biochemical production. PubMed: Comparison of fermented soybean paste (Doenjang) prepared by different methods based on profiling of volatile compounds. PubMed: 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. PubMed: Interaction Mechanisms between guaiacols and lignin: the conjugated double bond makes the difference. PubMed: Sorptive extraction with in-sample acetylation for gas chromatography-mass spectrometry determination of ethylphenol species in wine samples. PubMed: Optimisation of a simple and reliable method based on headspace solid-phase microextraction for the determination of volatile phenols in beer. PubMed: Use of microfungi in the treatment of oak chips: possible effects on wine. PubMed: Effect of halotolerant starter microorganisms on chemical characteristics of fermented chum salmon (Oncorhynchus keta) sauce. PubMed: Genome shuffling of Zygosaccharomyces rouxii to accelerate and enhance the flavour formation of soy sauce. PubMed: Inhibition by 2-methoxy-4-ethylphenol of Ca2+ influx through acquired and native N-methyl-D-aspartate-receptor channels. PubMed: Headspace solid-phase microextraction for direct determination of volatile phenols in cider. PubMed: Production of 4-ethylphenol from 4-hydroxycinnamic acid by Lactobacillus sp. isolated from a swine waste lagoon. PubMed: Identification and characterization of Dekkera bruxellensis, Candida pararugosa, and Pichia guilliermondii isolated from commercial red wines. PubMed: Spoilage yeasts in Patagonian winemaking: molecular and physiological features of Pichia guilliermondii indigenous isolates. PubMed: Chemical causes of the typical burnt smell after accidental fires. PubMed: Volatile composition of Merlot wine from different vine water status. PubMed: Minimization of ethylphenol precursors in red wines via the formation of pyranoanthocyanins by selected yeasts. PubMed: Molecular identification of Brettanomyces bruxellensis strains isolated from red wines and volatile phenol production. PubMed: Genetic diversity and physiological traits of Brettanomyces bruxellensis strains isolated from Tuscan Sangiovese wines. PubMed: Comparison of two SPME fibers for the extraction of some off-flavor cork-taint compounds in bottled wines investigated by GC-HRMS. PubMed: Prediction of sensory properties of Brazilian Arabica roasted coffees by headspace solid phase microextraction-gas chromatography and partial least squares. PubMed: Effects of elevated CO2 on grapevine (Vitis vinifera L.): volatile composition, phenolic content, and in vitro antioxidant activity of red wine. PubMed: Relationships between sensory descriptors, consumer acceptability and volatile flavor compounds of American dry-cured ham. PubMed: Smoke-derived taint in wine: the release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke. PubMed: Partial vinylphenol reductase purification and characterization from Brettanomyces bruxellensis. PubMed: Physiological and oenological traits of different Dekkera/Brettanomyces bruxellensis strains under wine-model conditions. PubMed: Comparison of metal oxide-based electronic nose and mass spectrometry-based electronic nose for the prediction of red wine spoilage. PubMed: 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. PubMed: Smoke-derived taint in wine: effect of postharvest smoke exposure of grapes on the chemical composition and sensory characteristics of wine. 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PubMed: 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. PubMed: Discovery of a eugenol oxidase from Rhodococcus sp. strain RHA1. PubMed: A 4-alkyl-substituted analogue of guaiacol shows greater repellency to savannah tsetse (Glossina spp.). PubMed: Determination of volatile phenols in wine using high-performance liquid chromatography with a coulometric array detector. PubMed: Characterization of aroma compounds in apple cider using solvent-assisted flavor evaporation and headspace solid-phase microextraction. PubMed: Determination of ethylphenols in wine by in situ derivatisation and headspace solid-phase microextraction-gas chromatography-mass spectrometry. PubMed: Determination of Brett character responsible compounds in wines by using multiple headspace solid-phase microextraction. 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PubMed: 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. PubMed: Fungal laccase-catalyzed degradation of hydroxy polychlorinated biphenyls. PubMed: Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium quality spanish aged red wines. PubMed: Characterization of odor-active compounds in Californian chardonnay wines using GC-olfactometry and GC-mass spectrometry. PubMed: Wood creosote, the principal active ingredient of seirogan, an herbal antidiarrheal medicine: a single-dose, dose-escalation safety and pharmacokinetic study. PubMed: Extraction and formation dynamic of oak-related volatile compounds from different volume barrels to wine and their behavior during bottle storage. PubMed: Determination of 4-ethylguaiacol and 4-ethylphenol in red wines using headspace-solid-phase microextraction-gas chromatography. PubMed: Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions. PubMed: Immobilized salt-tolerant yeasts: application of a new polyethylene-oxide support in a continuous stirred-tank reactor for flavour production. PubMed: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. PubMed: Measurement of urinary methoxyphenols and their use for biological monitoring of wood smoke exposure. PubMed: Solid-phase microextraction method development for headspace analysis of volatile flavor compounds. PubMed: Interactions between anthocyanins and aroma substances in a model system. Effect on the flavor of grape-derived beverages. PubMed: Quantitative analysis of 4-ethylphenol and 4-ethylguaiacol in red wine. PubMed: Potent odorants of raw Arabica coffee. Their changes during roasting. PubMed: [Anti-dermaptophyte activity of phenolic compounds in "mokusaku-eki"]. PubMed: Suppression of intestinal smooth muscle contraction by 4-ethylguaiacol, a constituent of wood creosote. PubMed: 2-Methylthiazolidine and 4-ethylguaiacol, male sex pheromone components of the cockroachNauphoeta cinerea (dictyoptera, blaberidae): A reinvestigation. PubMed: Suppression of intestinal smooth muscle contraction by phenolic compounds. PubMed: Analysis of beechwood creosote by gas chromatography-mass spectrometry and high-performance liquid chromatography.