4-methyl guaiacol

phenol, 2-methoxy-4-methyl-

CAS: 93-51-6 C8 H10 O2 MW: 138.16610000 spicy spicy

Identification

Name4-methyl guaiacol
IUPAC2-methoxy-4-methylphenol
CAS Number93-51-6
EINECS202-252-9
FDA UNIIW9GW1KZG6N
Molecular FormulaC8 H10 O2
Molecular Weight138.16610000
MDL NumberMFCD00002378
Nikkaji NumberJ1.175D
Beilstein1862340
CoE Number175
XlogP31.30 (est)

Regulatory

JECFA Food Flavoring715 2-methoxy-4-methylphenol
DG SANTE Food Flavourings04.007 2-methoxy-4-methylphenol
FEMA Number2671
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)93-51-6 ; 2-METHOXY-4-METHYLPHENOL
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

Physical Properties

Appearance pale yellow clear liquid (est)
Assay 98.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 1.09000 to 1.10000 @ 25.00 °C.
Pounds per Gallon - (est). 9.070 to 9.153
Refractive Index 1.53400 to 1.54000 @ 20.00 °C.
Melting Point 5.00 °C. @ 760.00 mm Hg
Boiling Point 221.00 to 222.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.078000 mmHg @ 25.00 °C. (est)
Flash Point 211.00 °F. TCC ( 99.44 °C. )
logP (o/w) 1.925 (est)
Shelf Life 24.00 month(s) or longer if stored properly.
Storage store in cool, dry place in tightly sealed containers, protected from heat and light.
Soluble in alcohol

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength medium ,
Substantivity 132 hour(s) at 10.00 % in dipropylene glycol
Odor Description
at 10.00 % in dipropylene glycol.
at 1.00 % in ethyl alcohol.
carnation; cheese; chocolate; clove; jasmine; sweet; vanilla; meaty; woody; wine-like; green; smoky; coffee
sweet, spicy/phenolic vanilla
sweet-spicy, phenolic-leathery note, floral balsamic undertones
aromatic, spicy, clove, vanilla, phenolic, smoke-like
sweet, smoky, leathery fragrance with hints of vanilla and cloves
Odor sample from Advanced Biotech. Inc.
Taste Description
spicy clove woody leathery smoky coffee phenolic cocoa burnt
at 10.00 ppm.
spicy
phenolic, smoky, sweet, coffee, vanilla, cocoa
spicy, medicinal; vanilla, clove-like with phenolic nuances

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 740 mg/kg
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
IFRA Critical EffectDermal sensitization
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%)Category 1: Products applied to the lips
NotesIFRA FLAVOR REQUIREMENTS:
Maximised Survey-derived Daily Intakes (MSDI-EU)31.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA)3.00 (μg/capita/day)
baked goods4.00000
beverages(nonalcoholic)10.00000
beverages(alcoholic)0.60000
breakfast cereal-
cheese-
chewing gum15.00000
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy1.00000
fruit ices-
gelatins / puddings7.00000
granulated sugar-
gravies-
hard candy0.80000
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products12.00000
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy4.00000
soups-
sugar substitutes-
sweet sauces-

Advanced Biotech. Inc.

Inspired by Nature

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Beijing Lys Chemicals Co, LTD.

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Endeavour Specialty Chemicals Ltd

Expertise in high impact aroma chemicals

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Foreverest Resources Ltd.

Leading pine based chemicals supplier

Supplying turpentine based and natural/extracted flavor & fragrance ingredients.

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Jiangyin Healthway International Trade Co., Ltd

Independent Ingredients Supplier

We provide custom synthesis and contract manufacturing from milligrams to metric tonnes.

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Lluch Essence S.L.

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M&U International LLC

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Moellhausen S.P.A.

THE CHEMISTRY OF EMOTIONS

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Natural Advantage

Manufacturer of natural flavor ingredients

With over 25 years experience in the flavor and food ingredient industries.

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OQEMA

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Penta International Corporation

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Riverside Aromatics Ltd.

Speciality Aroma Chemicals, Naturals and Synthetics

A specialist supplier of raw materials to the flavour industry.

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Robinson Brothers Limited

Providing Excellence in Chemistry

Award-winning UK chemical manufacturer of chemical intermediates and high-impact aroma chemicals.

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Sigma-Aldrich

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Sunaux International

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Symrise AG

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Synerzine, Inc.

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TCI AMERICA

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R C Treatt and Co Ltd

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Qingdao Free Trade Zone United International Co Ltd

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Ernesto Ventós S.A.

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Vigon International

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Potential Uses

FR anise FL bacon FL/FR beech FL beverage FR castoreum FL cheese FL chocolate cocoa FR clove FR coffee confection FL dairy FR jasmin FL meat smoked meat FL nut FR root beer FL rum FR saffron FL salmon smoked salmon FL savory FL smoke FR strawberry FL tomato FR vanilla FL whiskey FR ylang ylang

Natural Occurrence

anise plant anise seed beechwood tar beer PMC champaca concrete @ 0.02% Data cheese gruyere cheese PMC clover yellow sweet clover cocoa coffee PMC corn seed hyacinthus orientalis absolute @ 0.02-0.04% Data jasmin flower malt PMC mushroom PMC pepper bell pepper fruit pork PMC rum PMC sherry PMC smoked foods PMC tea vanilla bourbon vanilla whiskey bourbon whiskey wine red wine wine white wine ylang ylang oil @ 0.07% Data ylang ylang oil CO2 extract @ 0.01% Data

Synonyms

homo catechol monomethyl ether creosol p- creosol para- creosol creosol natural homo guaiacol guaiacol, 4-methyl- 1- hydroxy-2-methoxy-4-methyl benzene 1- hydroxy-2-methoxy-4-methylbenzene 4- hydroxy-3-methoxy-1-methyl benzene 4- hydroxy-3-methoxytoluene 4- hydroxy-3-methylanisol 2- hydroxy-5-methylanisole 2- methoxy-4-cresol 3- methoxy-4-hydroxytoluene 2- methoxy-4-methyl phenol 2- methoxy-4-methylphenol 2- methoxy-4-methylphenol natural 2- methoxy-p-cresol 2- methoxy-para-cresol 4- methyl guaiacol nat.4- methyl guaiacol p- methyl guaiacol para- methyl guaiacol 4- methyl guaiacol natural 4- methyl guaiacol synthetic 4- methyl-2-methoxyphenol 4- methylguaiacol p- methylguaiacol para- methylguaiacol phenol, 2-methoxy-4-methyl- rohkcrsol valspice (Givaudan) valspice natural PubMed: Volatile composition and sensory properties of Vanilla × tahitensis bring new insights for vanilla quality control. PubMed: Effect of Carbonyl Inhibitors and Their H2O 2 Detoxification on Lactic Acid Fermentation. PubMed: Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII). PubMed: Spectrophotometric determination of irrigant extrusion using passive ultrasonic irrigation, EndoActivator, or syringe irrigation. PubMed: Microwave-assisted deuterium exchange: the convenient preparation of isotopically labelled analogues for stable isotope dilution analysis of volatile wine phenols. PubMed: Hydrogenation of biofuels with formic acid over a palladium-based ternary catalyst with two types of active sites. PubMed: Determination of the importance of in-mouth release of volatile phenol glycoconjugates to the flavor of smoke-tainted wines. PubMed: Extraction of phenols from lignin microwave-pyrolysis oil using a switchable hydrophilicity solvent. PubMed: Ion permeability of artificial membranes evaluated by diffusion potential and electrical resistance measurements. PubMed: Bamboo vinegar decreases inflammatory mediator expression and NLRP3 inflammasome activation by inhibiting reactive oxygen species generation and protein kinase C-α/δ activation. PubMed: Ultraviolet spectroscopy of fundamental lignin subunits: guaiacol, 4-methylguaiacol, syringol, and 4-methylsyringol. PubMed: Polycyclic aromatic hydrocarbons (PAH) and phenolic substances in meat products smoked with different types of wood and smoking spices. PubMed: In chemico evaluation of prohapten skin sensitizers: behavior of 2-methoxy-4-(¹³C)methylphenol in the peroxidase peptide reactivity assay (PPRA) as an alternative to animal testing. PubMed: Synthesis, characterization, and cure chemistry of renewable bis(cyanate) esters derived from 2-methoxy-4-methylphenol. PubMed: Exposure of grapes to smoke of vegetation with varying lignin composition and accretion of lignin derived putative smoke taint compounds in wine. PubMed: Rapid discrimination and characterization of vanilla bean extracts by attenuated total reflection infrared spectroscopy and selected ion flow tube mass spectrometry. PubMed: Contribution of several volatile phenols and their glycoconjugates to smoke-related sensory properties of red wine. PubMed: Synthesis of renewable bisphenols from creosol. PubMed: Classification of smoke tainted wines using mid-infrared spectroscopy and chemometrics. PubMed: Contents of polycyclic aromatic hydrocarbons (PAH) and phenolic substances in Frankfurter-type sausages depending on smoking conditions using glow smoke. PubMed: Shoo fly, don't bother me! Efficacy of traditional methods of protecting cattle from tsetse. PubMed: Occupational exposure to phenolic compounds at coke plants--urinary excretion of methoxyphenols as an indicator of exposure to methoxyphenols. PubMed: Field trial of a synthetic tsetse-repellent technology developed for the control of bovine trypanosomosis in Kenya. PubMed: Preferential inhibition by antidiarrheic 2-methoxy-4-methylphenol of Ca(2+) influx across acquired N-methyl-D-aspartate receptor channels composed of NR1/NR2B subunit assembly. PubMed: Determination of Eucalyptus spp lignin S/G ratio: a comparison between methods. PubMed: Photochemistry of tricyclo[5.2.2.0(2,6)]undeca-4,10-dien-8-ones: an efficient general route to substituted linear triquinanes from 2-methoxyphenols. Total synthesis of (+/-)-Delta(9(12))-capnellene. PubMed: Volatile composition of Merlot wine from different vine water status. PubMed: Smoke-derived taint in wine: the release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke. PubMed: Stereocontrolled synthesis of polyfunctionalized cis-decalins from 2-methoxyphenols: total syntheses of (+/-)-eremopetasidione, (+/-)-3 beta-angeloyloxyfuranoeremophilane, and (+/-)-3 beta-methacryloyloxyfuranoeremophilane. PubMed: Smoke-derived taint in wine: effect of postharvest smoke exposure of grapes on the chemical composition and sensory characteristics of wine. PubMed: 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. PubMed: Cytoprotective properties of phenolic antidiarrheic ingredients in cultured astrocytes and neurons of rat brains. PubMed: A 4-alkyl-substituted analogue of guaiacol shows greater repellency to savannah tsetse (Glossina spp.). PubMed: Tsetse and other biting fly responses to Nzi traps baited with octenol, phenols and acetone. PubMed: Oral administration of phenolic antidiarrheic ingredients prevents ovariectomy-induced bone loss. PubMed: Thermal stabilization of levoglucosan in aromatic substances. PubMed: Flavor characteristics of lapsang souchong and smoked lapsang souchong, a special Chinese black tea with pine smoking process. PubMed: Occupational exposure to toluene and its possible causative role in renal damage development in shoe workers. PubMed: Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin. 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: Degradation of phenol and cresols at low temperatures using a suspended-carrier biofilm process. PubMed: Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B. PubMed: Wood creosote, the principal active ingredient of seirogan, an herbal antidiarrheal medicine: a single-dose, dose-escalation safety and pharmacokinetic study. PubMed: Simultaneous determination of 2-methoxyphenol, 2-methoxy-4-methylphenol, 2,6-dimethoxyphenol and 4'-hydroxy-3'-methoxyacetophenone in urine by capillary gas chromatography. PubMed: Extraction and formation dynamic of oak-related volatile compounds from different volume barrels to wine and their behavior during bottle storage. PubMed: [Wood creosote: a historical study and its preparation in combination with herbal drugs]. PubMed: Lack of oncogenicity of wood creosote, the principal active ingredient of Seirogan, an herbal antidiarrheal medication, in Sprague-Dawley rats. PubMed: The first total synthesis of (+/-)-eremopetasidione. PubMed: Enzymatic synthesis of vanillin. 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: Comparison of the antidiarrheal effects of wood creosote and loperamide in the rat jejunum and colon in vitro. PubMed: Anti-diarrhoeal effects of seirogan in the rat small intestine and colon examined in vitro. PubMed: Urinary excretion of phenols as an indicator of occupational exposure in the coke-plant industry. PubMed: Pharmacokinetics of wood creosote: glucuronic acid and sulfate conjugation of phenolic compounds. PubMed: The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides: evidence that extended pi-conjugation dramatically stabilizes the quinone methide formed from eugenol. PubMed: o-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices. PubMed: Xylosylation of Phenolic Hydroxyl Groups of the Monomeric Lignin Model Compounds 4-Methylguaiacol and Vanillyl Alcohol by Coriolus versicolor. PubMed: Suppression of intestinal smooth muscle contraction by phenolic compounds. PubMed: Enzymic oxidation of capsaicin. PubMed: Application of the MTT colorimetric assay to measure cytotoxic effects of phenolic compounds on established rat dental pulp cells. PubMed: Analysis of beechwood creosote by gas chromatography-mass spectrometry and high-performance liquid chromatography. PubMed: Nuclear magnetic resonance studies on the spatial relationship of aromatic donor molecules to the heme iron of horseradish peroxidase. PubMed: [Suicide by schizophrenic patients in psychiatric hospitals]. PubMed: [Cresol burns in the eye (author's transl)]. PubMed: The cell envelope of the Legionnaires' disease bacterium. Morphologic and biochemical characteristics. PubMed: The metabolism of vanillin and isovanillin in the rat.