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General Material Information

Preferred name methyl isoeugenol
Trivial Name Methylisoeugenol
Short Description 1,2-dimethoxy-4-(prop-1-enyl)benzene
Formula C11 H14 O2
CAS Number 93-16-3
FEMA Number 2476
ECHA Number 202-224-6
FDA UNII 46RN7Q97DE
Beilstein Number 0880472
MDL MFCD00009282
COE Number 186
NMR Predictor External link
JECFA Food Flavoring 1266 isoeugenyl methyl ether
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 93-16-3 ; ISOEUGENYL METHYL ETHER
Synonyms
  • benzene, 1,2-dimethoxy-4-(1-propen-1-yl)-
  • 3,4-dimethoxy-1,1-propen-1-yl benzene
  • 1,2-dimethoxy-4-(1-propen-1-yl) benzene
  • 1,2-dimethoxy-4-(1-propenyl) benzene
  • 1,2-dimethoxy-4-(1-propenyl)-benzene
  • 1,2-dimethoxy-4-(1-propenyl)benzene
  • 1,2-dimethoxy-4-(prop-1-en-1-yl)benzene
  • 1,2-dimethoxy-4-(prop-1-enyl)benzene
  • 1,2-dimethoxy-4-prop-1-enylbenzene
  • 1,2-dimethoxy-4-propen-1-yl benzene
  • 1-(3,4-dimethoxyphenyl)-1-propene
  • 3-(3,4-dimethoxyphenyl)-2-propene
  • 3,4-dimethoxypropylbenzene
  • ether, isoeugenyl methyl
  • iso eugenol methyl
  • 1,3,4-iso eugenol methyl ether
  • iso eugenol methyl ether
  • iso- eugenol methyl ether
  • iso eugenyl methyl ether
  • methyl iso eugenol
  • methylisoeugenol
  • 4-prop-1-enyl veratrole
  • 4-prop-1-enylveratrole
  • 4-propenyl veratrole
  • 4-(1-propenyl)-1,2-dimethoxybenzene
  • 4-propenylveratrole
  • 1-veratryl-1-propene
  • 1,2-dimethoxy-4-prop-1-enylbenzene
  • Benzene, 1,2-dimethoxy-4-propenyl-
  • Benzene, 1,2-dimethoxy-4-(1-propenyl)-
  • Veratrole, 4-propenyl-
  • 1,2-Dimethoxy-4-(1-propen-1-yl)benzene
  • Isoeugenol methyl ether
  • Isoeugenyl methyl ether
  • Isohomogenol
  • 4-Propenylveratrole
  • O-Methylisoeugenol
  • 1-(3,4-Dimethoxyphenyl)-1-propene
  • 3,4-Dimethoxypropenylbenzene
  • 4-Propenyl-1,2-dimethoxybenzene
  • 1-Veratryl-1-propene
  • 1,2-Dimethoxy-4-(1-propenyl)benzene
  • 3-(3,4-Dimethoxyphenyl)-2-propene
  • 4-(1-Propenyl)-1,2-dimethoxybenzene
  • NSC 46111
  • 3,4-Dimethoxy-β-methylstyrene
  • 1,2-Dimethoxy-4-propeneylbenzene

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

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Literature & References

1,2-dimethoxy-4-prop-1-enylbenzene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:93-16-3
Pubchem (cid):7128
Pubchem (sid):134972689
Pherobase:View
Publications by PubMed
Chemical compositions, phytotoxicity, and biological activities of Acorus calamus essential oils from Nepal.
Characterization of a self-sufficient trans-anethole oxygenase from Pseudomonas putida JYR-1.
Utility of rat liver S9 fractions to study skin-sensitizing prohaptens in a modified KeratinoSens assay.
Synthesis, spectroscopic characterization and DFT calculations of β-O-4 type lignin model compounds.
Neural coding of binary mixtures in a structurally related odorant pair.
Production of natural fragrance aromatic acids by coexpression of trans-anethole oxygenase and p-anisaldehyde dehydrogenase genes of Pseudomonas putida JYR-1 in Escherichia coli.
Isolation of a gene responsible for the oxidation of trans-anethole to para-anisaldehyde by Pseudomonas putida JYR-1 and its expression in Escherichia coli.
Involvement of 5-HT1A in the anxiolytic-like effect of dichloromethane fraction of Pimenta pseudocaryophyllus.
A hexane fraction of guava Leaves (Psidium guajava L.) induces anticancer activity by suppressing AKT/mammalian target of rapamycin/ribosomal p70 S6 kinase in human prostate cancer cells.
Chemical composition of the essential oil of aerial parts of Haussknechtia elymaitica Boiss. from Iran: a good natural source for trans-asaron.
Chemical composition, antinociceptive and anti-inflammatory properties of essential oil from the roots of Illicium lanceolatum.
Major constituents and antimicrobial activity of Korean herb Acorus calamus.
Terpenoid composition and antifungal activity of three commercially important essential oils against Aspergillus flavus and Aspergillus niger.
Phosphoinositide 3-kinase-dependent antagonism in mammalian olfactory receptor neurons.
Chemical composition of the essential oil of Feronia elephantum Correa.
Natural compounds endowed with cholinergic or anticholinergic activity. Enhancement of acetylcholine release by a quaternary derivative of L-hyoscyamine.
[Studies on constituents of rootsanel leaves from Desmodium blandum and their cytotoxic activity against growth of several tumor cells].
Nematicidal Activity of Plant Essential Oils and Components From Ajowan (Trachyspermum ammi), Allspice (Pimenta dioica) and Litsea (Litsea cubeba) Essential Oils Against Pine Wood Nematode (Bursaphelenchus Xylophilus).
threo-2-(2,6-dimethoxyphenoxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,3-diol: a conformational study.
Evidence for positive selection on the floral scent gene isoeugenol-O-methyltransferase.
NTP Toxicology and Carcinogenesis Studies of Methyleugenol (CAS NO. 93-15-2) in F344/N Rats and B6C3F1 Mice (Gavage Studies).
Inhibition of nicotinic acetylcholine receptors and calcium channels by clozapine in bovine adrenal chromaffin cells.
Lignin peroxidase initiates O2-dependent self-propagating chemical reactions which accelerate the consumption of 1-(3',4'-dimethoxyphenyl)propene.
Antiproliferative constituents in umbelliferae plants. IV. Constituents in the fruits of Anthriscus sylvestris Hoffm.
Synthesis, structure and quantitative structure-activity relationships of sigma receptor ligands, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl) piperazines.
A 28-day feeding study with methyl isoeugenol in rats.
Semiochemical attractants ofDiabrotica undecimpunctata howardi barber, southern corn rootworm, andDiabrotica virgifera virgifera leconte, the western corn rootworm (Coleoptera: Chrysomelidae).
Influence of vehicles on penetration through human epidermis of benzyl alcohol, isoeugenol and methyl isoeugenol.

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
KEGG (GenomeNet):C10478
HMDB (The Human Metabolome Database):HMDB41553
FooDB:FDB021536
Export Tariff Code:2909.30.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 178.23098754883
Specific gravity @ 25 °C
Pounds per Gallon 8.712 to 8.779
Specific gravity @ 20 °C
Pounds per Gallon 8.731 to 8.797
Refractive Index 1.566 to 1.569 @ 20 °C
Melting Point 16 to 17°C @ 760 mm Hg
Boiling Point 262 to 264°C @ 760 mm Hg
Vapor Pressure 0.011 mmHg @ 25 °C
Flash Point TCC Value 104.44 °C TCC
logP (o/w) 3.049 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
fixed oils Yes
paraffin oil Yes
water, 169.1 mg/L @ 25 °C (est) Yes
glycerin No
propylene glycol No
Stability
non-discoloring in most media Unspecified

Organoleptic Properties

Odor Type: Spicy
spicy, clove, floral, carnation, woody
Odor strength medium
Substantivity 240 hour(s) at 100.00 %
Luebke, William tgsc, (1988) At 100.00 %. spicy clove blossom carnation woody
Flavor Type: Spicy
spicy, clove, resinous, galanga, smoky, woody, powdery
Luebke, William tgsc, (1988) Spicy warm clove resinous galanga smoky woody powdery
Useful in: brown others, vanilla, savory spices, fruity red, fruity yellow, fruity tropical, sweet others, alcoholics. Spicy, woody, smoky, tar-like
General comment Spicy, woody, smoky, fatty

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Human Experience:
8 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 2500 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 865, 1975.

intravenous-mouse LD50 181 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 199, Pg. 226, 1972.

intraperitoneal-mouse LD50 570 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 199, Pg. 226, 1972.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 865, 1975.

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 methyl isoeugenol usage levels up to:
8.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 109.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 129.00 (μg/capita/day)
Structure Class: III
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: -18.00000
beverages(nonalcoholic): -4.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -110.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -7.70000
fruit ices: -7.70000
gelatins / puddings: -0.10000
granulated sugar: --
gravies: --
hard candy: -13.00000
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):

Scientific Opinion on Flavouring Group Evaluation 81 (FGE.81): Consideration of hydroxypropenylbenzenes evaluated by JECFA (61st meeting) structurally related to 2-methoxy-4-(prop-1-enyl)phenyl 3-methylbutyrate from chemical group 17 evaluated by EFSA in FGE.30
View page or View pdf

Scientific Opinion on the safety and efficacy of aromatic ethers including anisole derivatives (chemical group 26) when used as feed additives for all animal species
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):93-16-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7128
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
1,2-dimethoxy-4-prop-1-enylbenzene
Chemidplus:0000093163
RTECS:CZ7000000 for cas# 93-16-3