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2-methoxy-4-vinyl phenol

Chemical Structure

General Material Information

Preferred name 2-methoxy-4-vinyl phenol
Trivial Name 4-Vinylguaiacol
Short Description 2-methoxy-4-vinylphenol
Formula C9 H10 O2
CAS Number 7786-61-0
FEMA Number 2675
Flavis Number 4.009
ECHA Number 232-101-2
FDA UNII DA069CTH0O
Nikkaji Number J134.783G
Beilstein Number 2044521
MDL MFCD00015437
COE Number 177
NMR Predictor External link
JECFA Food Flavoring 725 2-methoxy-4-vinylphenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 7786-61-0 ; 2-METHOXY-4-VINYLPHENOL
Synonyms
  • 4-ethenyl-2-methoxyphenol
  • guaiacol, 4-vinyl-
  • 2-hydroxy-3-methoxystyrene
  • 4-hydroxy-3-methoxystyrene
  • 4-hydroxy-3-methoxyvinyl benzene
  • 4-hydroxy-3-methoxyvinylbenzene
  • 2-methoxy-4-ethenylphenol
  • 3-methoxy-4-hydroxystyrene
  • 2-methoxy-4-vinyl phenol
  • 2-methoxy-4-vinylphenol
  • o- methoxy-p-vinylphenol
  • phenol, 2-methoxy-4-vinyl-
  • phenol, 4-ethenyl-2-methoxy-
  • phenol, 4-vinyl-2-methoxy-
  • varamol (IFF)
  • varamol-106 (IFF)
  • p- vinyl catechol-o-methyl ether
  • para- vinyl catechol-ortho-methyl ether
  • 4-vinyl guaiacol
  • p- vinyl guaiacol
  • para- vinyl guaiacol
  • 4-vinyl guaiacol natural 1% in ethyl acetate
  • 4-vinyl guaiacol natural 1% in ethyl alcohol
  • 4-vinyl guaiacol natural 1% in P.G.
  • 4-vinyl guaiacol natural 5% in ethyl acetate
  • 4-vinyl guaiacol natural 5% in ethyl alcohol
  • 4-vinyl guaiacol natural 5% in P.G.
  • 4-vinyl-2-methoxy-phenol
  • 4-vinyl-2-methoxyphenol
  • 4-vinyl-guaiacol
  • p- vinylcatechol-o-methyl ether
  • vinylcatechol-O-methyl ether, p-
  • 4-vinylguaiacol
  • p- vinylguaiacol
  • para- vinylguaiacol
  • 4-vinylguaiacol 10% in PG.
  • 4-vinylguaiacol in 10% P.G.
  • vinylguaiacol natural 10% in triacetin
  • 4-vinylguaiacol pure
  • 4-ethenyl-2-methoxyphenol
  • 2-Methoxy-4-vinylphenol
  • 4-Vinylguaiacol
  • o-Methoxy-p-vinylphenol
  • p-Vinylguaiacol
  • 4-Hydroxy-3-methoxyvinylbenzene
  • 3-Methoxy-4-hydroxystyrene
  • 4-Hydroxy-3-methoxystyrene
  • 4-Vinyl-2-methoxyphenol
  • 2-Methoxy-4-ethenylphenol
  • Varamol 106
  • (4-Hydroxy-3-methoxyphenyl)ethene

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

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Literature & References

4-ethenyl-2-methoxyphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:7786-61-0
Pubchem (cid):332
Pubchem (sid):135019909
Flavornet:7786-61-0
Pherobase:View
Publications by PubMed
Characterization of the key aroma compounds in two bavarian wheat beers by means of the sensomics approach.
Evaluation of aroma differences between high-salt liquid-state fermentation and low-salt solid-state fermentation soy sauces from China.
[Chemical consitituents from root of Isatis indigotica].
Key aroma compounds in roasted in-shell peanuts.
Chemical characterization and acaricide potential of essential oil from aerial parts of Tagetes patula L. (Asteraceae) against engorged adult females of Rhipicephalus sanguineus (Latreille, 1806).
Characterization of the aroma signature of styrian pumpkin seed oil ( Cucurbita pepo subsp. pepo var. Styriaca) by molecular sensory science.
Identification of aroma active compounds of cereal coffee brew and its roasted ingredients.
Bioprocess design for the microbial production of natural phenolic compounds by Debaryomyces hansenii.
Production of vinyl derivatives from alkaline hydrolysates of corn cobs by recombinant Escherichia coli containing the phenolic acid decarboxylase from Lactobacillus plantarum CECT 748T.
Characterization of the key aroma compounds in rape honey by means of the molecular sensory science concept.
Anti-inflammatory effect of 2-methoxy-4-vinylphenol via the suppression of NF-κB and MAPK activation, and acetylation of histone H3.
Decarboxylation of ferulic acid to 4-vinyl guaiacol by Streptomyces setonii.
Analysis of essential oils from Scutellaria orientalis ssp. alpina and S. utriculata by GC and GC-MS.
Efficient synthesis of hydroxystyrenes via biocatalytic decarboxylation/deacetylation of substituted cinnamic acids by newly isolated Pantoea agglomerans strains.
Characterization of odor-active compounds of various cherry wines by gas chromatography-mass spectrometry, gas chromatography-olfactometry and their correlation with sensory attributes.
Characteristics of lignin from flax shives as affected by extraction conditions.
Cloning, sequencing, and overexpression in Escherichia coli of the Enterobacter sp. Px6-4 gene for ferulic acid decarboxylase.
Chemical composition and antimicrobial activity of volatiles from Degenia velebitica, a European stenoendemic plant of the Brassicaceae family.
2-Methoxy-4-vinylphenol can induce cell cycle arrest by blocking the hyper-phosphorylation of retinoblastoma protein in benzo[a]pyrene-treated NIH3T3 cells.
Changes in volatile aroma compounds of organic fragrant rice during storage under different conditions.
Volatile compounds and the changes in their concentration levels during storage in beers containing varying malt concentrations.
Identification of novel aroma-active thiols in pan-roasted white sesame seeds.
Volatile constituents of the aerial parts of white salsify (Tragopogon porrifolius L., Asteraceae).
Bioproduction of lauryl lactone and 4-vinyl guaiacol as value-added chemicals in two-phase biotransformation systems.
Analysis of essential oil from Teucrium maghrebinum Greuter et Burdet growing wild in Algeria.
Pharmacological activity of compounds extracted from persimmon peel (Diospyros kaki THUNB.).
Free and hydrolytically released volatile compounds of Vitis vinifera L. cv. Fiano grapes as odour-active constituents of Fiano wine.
[Insecticidal activity and active components of alcohol extract from Juglans mandshurica Maxim leaves].
Formation of 4-vinyl guaiacol as an intermediate in bioconversion of ferulic acid by Schizophyllum commune.
A structure-activity relationship study on a natural germination inhibitor, 2-methoxy-4-vinylphenol (MVP), in wheat seeds to evaluate its mode of action.
Changes in key odorants of raw coffee beans during storage under defined conditions.
[Extraction and determination of essential oils in Indocalamus latifolius leaves and Indocalamus tessellatus leaves].
Comparison of three lychee cultivar odor profiles using gas chromatography-olfactometry and gas chromatography-sulfur detection.
[Studies on the chemical constituents of the essential oil from the leaves of Dalbergia odorifera T. Chen].
[Contrastive analysis of volatile oil from Serissa serissoides in different seasons].
Impact odorants of different young white wines from the Canary Islands.
Effect of overexpression of Saccharomyces cerevisiae Pad1p on the resistance to phenylacrylic acids and lignocellulose hydrolysates under aerobic and oxygen-limited conditions.
Change in the flavor of black tea drink during heat processing.
Identification of potent odorants in Japanese green tea (Sen-cha).
Solid-phase extraction and HPLC determination of 4-vinyl guaiacol and its precursor, ferulic acid, in orange juice.
Compounds inhibiting prostaglandin synthesis isolated from Ipomoea pes-caprae.

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):C17883
HMDB (The Human Metabolome Database):HMDB13744
FooDB:FDB000857
YMDB (Yeast Metabolome Database):YMDB01624
Export Tariff Code:2909.50.0090
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 150.17709350586
Specific gravity @ 25 °C
Pounds per Gallon 9.195 to 9.278
Specific gravity @ 20 °C
Pounds per Gallon 9.205 to 9.289
Refractive Index 1.57 to 1.58 @ 20 °C
Refractive Index 1.57 to 1.584 @ 20 °C
Melting Point 25 to 29°C @ 760 mm Hg
Vapor Pressure 0.019 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 2.573 est
Solubility
alcohol Yes
water, 926 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Spicy
spicy, clove, carnation, phenolic, peppery, smoky, woody, powdery
Odor strength high , recommend smelling in a 0.10 % solution or less
Substantivity 240 hour(s) at 100.00 %
Luebke, William tgsc, (2021) At 0.10 % in dipropylene glycol. sweet spicy clove carnation phenolic peppery smoky woody powdery
Flavor Type: Spicy
spicy, powdery, clove, phenolic, woody, smoky, balsamic, amber
Luebke, William tgsc, (2021) Spicy powdery clove phenolic woody smoky balsamic amber
4-Vinylguaiacol is an important constituent in distilled spirits (whiskey, rum) where it contributes to the overall sweet smoky background notes. It also contributes to the flavour of Tobacco. Used in Coffee, Chocolate, Spice, Vanilla, Tea, Whiskey, Rum, Tobacco, Roasted Peanut and Strawberry flavors. Also used in Artificial Smoke flavors. This material is considered to be an important aroma contributor to "Traimener" wines. Normal use levels in finished consumer product: 0.05-1 ppm. Council of Europe limits: Foods (1 ppm); Beverages (1 ppm). Sweet
Useful in: brown cocoa, brown coffee, brown others, vanilla, savory meat, alcoholics. Clove, Smoky, Balsamic, Vanilla

Occurrences

Potential Uses

Applications
Odor purposes Apple, Chocolate, Coffee, Oriental, Patchouli, Peanut, Peanut, Saffron, Spice, Spice, Strawberry, Tobacco, Vanilla, Vetiver, Woody
Flavoring purposes Rum, Smoke, Tea, Tomato, Whiskey
Other purposes Topnotes
Cosmetic purposes Perfuming agents

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 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)
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 2-methoxy-4-vinyl phenol usage levels up to:
0.0500 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 2.60 (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: 20.0000024.00000
beverages(nonalcoholic): 2.000003.00000
beverages(alcoholic): 20.0000040.00000
breakfast cereal: --
cheese: --
chewing gum: 2.000005.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 4.0000011.00000
fruit ices: --
gelatins / puddings: 4.000006.00000
granulated sugar: --
gravies: 3.000006.00000
hard candy: 1.000008.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 3.000007.00000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 8.000009.00000
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
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):7786-61-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :332
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-ethenyl-2-methoxyphenol
Chemidplus:0007786610
RTECS:SL8205000 for cas# 7786-61-0