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4-methyl guaiacol

Chemical Structure

General Material Information

Preferred name 4-methyl guaiacol
Trivial Name 2-Methoxy-4-methylphenol
Short Description phenol, 2-methoxy-4-methyl-
Formula C8 H10 O2
CAS Number 93-51-6
FEMA Number 2671
Flavis Number 4.007
ECHA Number 202-252-9
FDA UNII W9GW1KZG6N
Nikkaji Number J1.175D
Beilstein Number 1862340
MDL MFCD00002378
COE Number 175
NMR Predictor External link
JECFA Food Flavoring 715 2-methoxy-4-methylphenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 93-51-6 ; 2-METHOXY-4-METHYLPHENOL
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
  • p-Cresol, 2-methoxy-
  • 2-Methoxy-4-methylphenol
  • Homoguaiacol
  • 4-Hydroxy-3-methoxy-1-methylbenzene
  • 4-Hydroxy-3-methoxytoluene
  • 2-Methoxy-p-cresol
  • p-Methylguaiacol
  • 4-Methylguaiacol
  • p-Creosol
  • 4-Methyl-2-methoxyphenol
  • 3-Methoxy-4-hydroxytoluene
  • NSC 4969
  • 3-Methoxy-4-hydroxybenzaldhyde
  • Methyl guaiacol
  • Methylguaiacol-4

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

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Literature & References

2-methoxy-4-methylphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:93-51-6
Pubchem (cid):7144
Pubchem (sid):134972998
Pherobase:View
Publications by PubMed
Volatile composition and sensory properties of Vanilla × tahitensis bring new insights for vanilla quality control.
Effect of Carbonyl Inhibitors and Their H2O 2 Detoxification on Lactic Acid Fermentation.
Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII).
Spectrophotometric determination of irrigant extrusion using passive ultrasonic irrigation, EndoActivator, or syringe irrigation.
Microwave-assisted deuterium exchange: the convenient preparation of isotopically labelled analogues for stable isotope dilution analysis of volatile wine phenols.
Hydrogenation of biofuels with formic acid over a palladium-based ternary catalyst with two types of active sites.
Determination of the importance of in-mouth release of volatile phenol glycoconjugates to the flavor of smoke-tainted wines.
Extraction of phenols from lignin microwave-pyrolysis oil using a switchable hydrophilicity solvent.
Ion permeability of artificial membranes evaluated by diffusion potential and electrical resistance measurements.
Bamboo vinegar decreases inflammatory mediator expression and NLRP3 inflammasome activation by inhibiting reactive oxygen species generation and protein kinase C-α/δ activation.
Ultraviolet spectroscopy of fundamental lignin subunits: guaiacol, 4-methylguaiacol, syringol, and 4-methylsyringol.
Polycyclic aromatic hydrocarbons (PAH) and phenolic substances in meat products smoked with different types of wood and smoking spices.
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.
Synthesis, characterization, and cure chemistry of renewable bis(cyanate) esters derived from 2-methoxy-4-methylphenol.
Exposure of grapes to smoke of vegetation with varying lignin composition and accretion of lignin derived putative smoke taint compounds in wine.
Rapid discrimination and characterization of vanilla bean extracts by attenuated total reflection infrared spectroscopy and selected ion flow tube mass spectrometry.
Contribution of several volatile phenols and their glycoconjugates to smoke-related sensory properties of red wine.
Synthesis of renewable bisphenols from creosol.
Classification of smoke tainted wines using mid-infrared spectroscopy and chemometrics.
Contents of polycyclic aromatic hydrocarbons (PAH) and phenolic substances in Frankfurter-type sausages depending on smoking conditions using glow smoke.
Shoo fly, don't bother me! Efficacy of traditional methods of protecting cattle from tsetse.
Occupational exposure to phenolic compounds at coke plants--urinary excretion of methoxyphenols as an indicator of exposure to methoxyphenols.
Field trial of a synthetic tsetse-repellent technology developed for the control of bovine trypanosomosis in Kenya.
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.
Determination of Eucalyptus spp lignin S/G ratio: a comparison between methods.
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.
Volatile composition of Merlot wine from different vine water status.
Smoke-derived taint in wine: the release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke.
Stereocontrolled synthesis of polyfunctionalized cis-decalins from 2-methoxyphenols: total syntheses of (+/-)-eremopetasidione, (+/-)-3 beta-angeloyloxyfuranoeremophilane, and (+/-)-3 beta-methacryloyloxyfuranoeremophilane.
Smoke-derived taint in wine: effect of postharvest smoke exposure of grapes on the chemical composition and sensory characteristics of wine.
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.
Cytoprotective properties of phenolic antidiarrheic ingredients in cultured astrocytes and neurons of rat brains.
A 4-alkyl-substituted analogue of guaiacol shows greater repellency to savannah tsetse (Glossina spp.).
Tsetse and other biting fly responses to Nzi traps baited with octenol, phenols and acetone.
Oral administration of phenolic antidiarrheic ingredients prevents ovariectomy-induced bone loss.
Thermal stabilization of levoglucosan in aromatic substances.
Flavor characteristics of lapsang souchong and smoked lapsang souchong, a special Chinese black tea with pine smoking process.
Occupational exposure to toluene and its possible causative role in renal damage development in shoe workers.
Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin.
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.
Degradation of phenol and cresols at low temperatures using a suspended-carrier biofilm process.
Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B.
Wood creosote, the principal active ingredient of seirogan, an herbal antidiarrheal medicine: a single-dose, dose-escalation safety and pharmacokinetic study.
Simultaneous determination of 2-methoxyphenol, 2-methoxy-4-methylphenol, 2,6-dimethoxyphenol and 4'-hydroxy-3'-methoxyacetophenone in urine by capillary gas chromatography.
Extraction and formation dynamic of oak-related volatile compounds from different volume barrels to wine and their behavior during bottle storage.
[Wood creosote: a historical study and its preparation in combination with herbal drugs].
Lack of oncogenicity of wood creosote, the principal active ingredient of Seirogan, an herbal antidiarrheal medication, in Sprague-Dawley rats.
The first total synthesis of (+/-)-eremopetasidione.
Enzymatic synthesis of vanillin.
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.
Comparison of the antidiarrheal effects of wood creosote and loperamide in the rat jejunum and colon in vitro.
Anti-diarrhoeal effects of seirogan in the rat small intestine and colon examined in vitro.
Urinary excretion of phenols as an indicator of occupational exposure in the coke-plant industry.
Pharmacokinetics of wood creosote: glucuronic acid and sulfate conjugation of phenolic compounds.
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.
o-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices.
Xylosylation of Phenolic Hydroxyl Groups of the Monomeric Lignin Model Compounds 4-Methylguaiacol and Vanillyl Alcohol by Coriolus versicolor.
Suppression of intestinal smooth muscle contraction by phenolic compounds.
Enzymic oxidation of capsaicin.
Application of the MTT colorimetric assay to measure cytotoxic effects of phenolic compounds on established rat dental pulp cells.
Analysis of beechwood creosote by gas chromatography-mass spectrometry and high-performance liquid chromatography.
Nuclear magnetic resonance studies on the spatial relationship of aromatic donor molecules to the heme iron of horseradish peroxidase.
[Suicide by schizophrenic patients in psychiatric hospitals].
[Cresol burns in the eye (author's transl)].
The cell envelope of the Legionnaires' disease bacterium. Morphologic and biochemical characteristics.
The metabolism of vanillin and isovanillin in the rat.

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
HMDB (The Human Metabolome Database):HMDB32136
FooDB:FDB008862
Export Tariff Code:2909.50.2000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 138.16610717773
Specific gravity @ 25 °C
Pounds per Gallon 9.07 to 9.153
Refractive Index 1.534 to 1.54 @ 20 °C
Boiling Point 221 to 222°C @ 760 mm Hg
Vapor Pressure 0.078 mmHg @ 25 °C
Flash Point TCC Value 99.44 °C TCC
logP (o/w) 1.925 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
water, 2093 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Spicy
spicy, clove, vanilla, phenolic, medicinal, leathery, woody, smoky, burnt, sweet, candy
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 132 hour(s) at 10.00 % in dipropylene glycol
Luebke, William tgsc, (2021) At 10.00 % in dipropylene glycol. spicy clove vanilla phenolic medicinal leathery woody smoky burnt
Mosciano, Gerard P&F 23, No. 6, 31, (1998) At 1.00 % in ethyl alcohol. Sweet, candy, spice, eugenol, vanilla, leather, spicy, smoky
Flavor Type: Spicy
spicy, clove, woody, leathery, smoky, coffee, phenolic, cocoa, burnt, vanilla, chemical
Luebke, William tgsc, (2021) Spicy clove woody leathery smoky coffee phenolic cocoa burnt
Mosciano, Gerard P&F 23, No. 6, 31, (1998) At 10.00 ppm. VaniIla, spice, eugenol, woody and leather nuances with no residual chemical notes
Used in rum, nut, clove, vanilla flavours for savoury at 35ppm, soft confection at 10ppm, beverages at 5ppm, and dairy confection/desserts at 2ppm. Spicy
Useful in: brown nuts, brown cocoa, brown coffee, brown others, dairy, vanilla, savory spices, savory meat, sweet others, alcoholics. Phenolic, smoky, sweet, coffee, vanilla, cocoa
General comment Spicy, medicinal; vanilla, clove-like with phenolic nuances

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
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 37/39 - Wear suitable 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 4), H302
Skin irritation (Category 2), H315
Eye irritation (Category 2A), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
H315 - Causes skin irritation
H319 - Causes serious eye irritation
H335 - May cause respiratory irritation
Precautionary statement(s)
P261 - Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P271 - Use only outdoors or in a well-ventilated area.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302 + P352 - IF ON SKIN: wash with plenty of soap and water.
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.
P312 - Call a POISON CENTER or doctor/physician if you feel unwell.
P330 - Rinse mouth.
P332 + P313 - IF SKIN irritation occurs: Get medical advice/attention.
P337 + P313 - IF eye irritation persists: Get medical advice/attention.
P362 - Take off contaminated clothing and wash before reuse.
P403 + P233 - Store in a well-ventilated place. Keep container tightly closed.
P405 - Store locked up.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
oral-rat LD50 740 mg/kg
Folia Medica Cracoviensia. Vol. 32, Pg. 309, 1991.

intravenous-mouse LD50 76 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 164, Pg. 30, 1966.

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
IFRA Critical Effect:
Dermal sensitization
View the IFRA Standard
View IFRA Standards Library for complete information.
Please review Amendment 49 IFRA documentation for complete information.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%):
Category 1: Products applied to the lips
0.0085 %
Category 2: Products applied to the axillae
0.0025 %
Category 3: Products applied to the face/body using fingertips
0.051 %
Category 4: Products related to fine fragrance
0.047 %
Category 5: Products applied to the face and body using the hands (palms), primarily leave-on
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on
0.012 %
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on
0.012 %
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on
0.012 %
Category 5D: Baby Creams, baby Oils and baby talc
0.012 %
Category 6: Products with oral and lip exposure
0.028 %
Category 7: Products applied to the hair with some hand contact
Category 7A: Rinse-off products applied to the hair with some hand contact
0.096 %
Category 7B: Leave-on products applied to the hair with some hand contact
0.096 %
Category 8: Products with significant anogenital exposure
0.005 %
Category 9: Products with body and hand exposure, primarily rinse off
0.092 %
Category 10: Household care products with mostly hand contact
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products)
0.33 %
Category 10B: Household aerosol/spray products
0.33 %
Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
0.18 %
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
0.18 %
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin
No Restriction
Notes:
IFRA FLAVOR REQUIREMENTS:

Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

Maximised Survey-derived Daily Intakes (MSDI-EU): 31.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 3.00 (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. Update in publication number(s): 29
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 4.0000011.00000
beverages(nonalcoholic): 10.0000021.00000
beverages(alcoholic): 0.6000010.00000
breakfast cereal: --
cheese: --
chewing gum: 15.0000025.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 1.000002.00000
fruit ices: --
gelatins / puddings: 7.0000018.00000
granulated sugar: --
gravies: --
hard candy: 0.800000.80000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 12.0000035.00000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 4.0000010.00000
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):93-51-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7144
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-methoxy-4-methylphenol
Chemidplus:0000093516
RTECS:GP1755000 for cas# 93-51-6