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vanillyl ethyl ether

Chemical Structure

General Material Information

Preferred name vanillyl ethyl ether
Trivial Name Vanillyl ethyl ether
Short Description ethyl 4-hydroxy-3-methoxybenzyl ether
Formula C10 H14 O3
CAS Number 13184-86-6
FEMA Number 3815
Flavis Number 4.094
ECHA Number 236-136-4
FDA UNII 1423UFT5P6
Nikkaji Number J213.731C
MDL MFCD06409999
NMR Predictor External link
JECFA Food Flavoring 887 vanillyl ethyl ether
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 13184-86-6 ; VANILLYL ETHYL ETHER
Synonyms
  • p- cresol, a-ethoxy-2-methoxy-
  • alpha- ethoxy-2-methoxy-p-cresol
  • alpha- ethoxy-2-methoxy-para-cresol
  • 4-( ethoxymethyl)-2-methoxyphenol
  • ethyl 4-hydroxy-3-methoxybenzyl ether
  • ethyl vanillyl ether
  • 4-hydroxy-3-methoxybenzyl ethyl ether
  • phenol, 4-(ethoxymethyl)-2-methoxy-
  • vanillin ethyl ether
  • 4-(ethoxymethyl)-2-methoxyphenol
  • p-Cresol, α-ethoxy-2-methoxy-
  • 4-Hydroxy-3-methoxybenzyl ethyl ether
  • Vanillyl alcohol ethyl ether

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

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Literature & References

4-(ethoxymethyl)-2-methoxyphenol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:13184-86-6
Pubchem (cid):61586
Pubchem (sid):135019038
Publications by US Patents
4,657,700 - Fragrance compositions containing benzyl ethers
Publications by PubMed
[Chemical constituents from tubers of Cremastra appendiculata].
[Chemical constituents of Cudrania cochinchinensis].
[Phenolic derivatives from Wisteria sinensis sweet caulis].
Inhibition of arachidonic acid metabolism by the Andean crude drug Parastrephia lucida (Meyen) Cabrera.
Inhibition of arachidonic acid metabolism by the Andean crude drug Parastrephia lucida (Meyen) Cabrera.
A study on anticancer activity of Caulis Spatholobi extract on human osteosarcoma Saos-2 cells.
Biodegradation of 2,4-dichlorophenol by shiitake mushroom (Lentinula edodes) using vanillin as an activator.
[Chemical constituents from aqueous extract of Gastrodia elata].
Effects of glucam P-20, vanillin, and fixolide on mosquito repellency of citronella oil lotions.
Simultaneous determination of five active compounds in chimonanthus nitens by double-development HPTLC and scanning densitometry.
Lignin structural variation in hardwood species.
Triacylglyceride measurement in small quantities of homogenised insect tissue: comparisons and caveats.
Artificial aging of Uva di Troia and Primitivo wines using oak chips inoculated with Penicillium purpurogenum.
Identification of DypB from Rhodococcus jostii RHA1 as a lignin peroxidase.
Improved iterative synthesis of linearly disassembling dendrons.
Physicochemical, nutritional, and functional characterization of fruits xoconostle (Opuntia matudae) pears from Central-México Region.
Total synthesis of (+)-schweinfurthins B and E.
A rapid and precise method for determination of D/H ratios of plant methoxyl groups.
[Studies on the chemical constituents of Litsea lancifolia].
Qualitative and quantitative analysis of four species of Curcuma rhizomes using twice development thin layer chromatography.
Oxidation of lignin using aqueous polyoxometalates in the presence of alcohols.
Evaluation of a Hypocrea jecorina enzyme preparation for hydrolysis of Tifton 85 bermudagrass.
Vanillin, 4-hydroxybenzyl aldehyde and 4-hydroxybenzyl alcohol prevent hippocampal CA1 cell death following global ischemia.
Protective effects of several components of Gastrodia elata on lipid peroxidation in gerbil brain homogenates.
[Chemical constituents from roots of Ardisia punctata].
In vitro androgenicity in pulp and paper mill effluents.
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.
Application of solid-phase extraction for determination of phenolic compounds in barrique wines.
Guaiacylglycerol-7'-O-methyl 8'-vanillic acid ether and related compounds from Boreava orientalis.
Chemical analysis and antifungal activity of the essential oil of Calea clematidea.
Maturing wines in oak barrels. Effects of origin, volume, and age of the barrel on the wine volatile composition.
Production of oxychemicals from precipitated hardwood lignin.
Formation and Degradation of Furfuryl Alcohol, 5-Methylfurfuryl Alcohol, Vanillyl Alcohol, and Their Ethyl Ethers in Barrel-Aged Wines.
Inhibition of oxidation of human low-density lipoproteins by phenolic substances in different essential oils varieties.
Network of C-H...O interactions in 4-benzyloxy-3-methoxybenzaldehyde (vanillin benzyl ether).
Characterization of the key aroma compounds in dried fruits of the West African peppertree Xylopia aethiopica (Dunal) A. Rich (Annonaceae) using aroma extract dilution analysis.
Concentrations of salinomycin in eggs and tissues of laying chickens fed medicated feed for 14 days followed by withdrawal for 3 days.
Oxidation of phenolic arylglycerol beta-aryl ether lignin model compounds by manganese peroxidase from Phanerochaete chrysosporium: oxidative cleavage of an alpha-carbonyl model compound.
Degradation of non-phenolic beta-o-4 lignin substructure model compounds by Acinetobacter sp.
Devil's-claw (Proboscidea louisianica), essential oil and its components : Potential allelochemical agents on cotton and wheat.
Thiol-mediated oxidation of nonphenolic lignin model compounds by manganese peroxidase of Phanerochaete chrysosporium.
Isolation and characterization of an anaerobic dehydrodivanillin-degrading bacterium.
[Simultaneous analysis of aromatic aldehydes and coumarins with high pressure liquid chromatography. Application to wines and brandies stored in oak barrels].
Anaerobic degradation of veratrylglycerol-beta-guaiacyl ether and guaiacoxyacetic acid by mixed rumen bacteria.
Alarm substances of the stingless bee,Trigona silvestriana.
Catabolism of arylglycerol-beta-aryl ethers lignin model compounds by Pseudomonas cepacia 122.
Whole-cell bioconversion of vanillin to vanillic acid by Streptomyces viridosporus.
Biosynthesis, deposition, and partial characterization of potato suberin phenolics.
Gas-chromatographic estimation of 3-methoxy-4-hydroxy phenylglycol after transformation to vanillin methoxime trimethylsilyl ether.
Gas-chromatographic estimation of urinary vanillylmandelic acid after transformation to vanillin methoxime trimethylsilyl ether.
[Benzoins, benzils and benzilic acids of o-vanillin- and o-novovanillin ether].

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
HMDB (The Human Metabolome Database):HMDB37641
FooDB:FDB016757
Export Tariff Code:2909.50.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 182.21917724609
Specific gravity @ 25 °C
Pounds per Gallon 9.203 to 9.261
Refractive Index 1.528 to 1.532 @ 20 °C
Vapor Pressure 0.003 mmHg @ 25 °C
Flash Point TCC Value 120 °C TCC
logP (o/w) 1.571 est
Solubility
alcohol Yes
water, 2262 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Chocolate
alcoholic, rummy, sweet, chocolate, creamy, vanilla, spicy, nutmeg, smoky
Odor strength medium
Substantivity > 400 hour(s) at 20.00 % in ethyl alcohol
Luebke, William tgsc, (2009) At 20.00 % in ethyl alcohol. alcoholic rum sweet chocolate creamy vanilla spicy nutmeg smoky
Flavor Type: Rummy
rummy, chocolate, creamy, vanilla
Luebke, William tgsc, (2009) Sweet rummy chocolate creamy vanilla

Occurrences

Potential Uses

Applications
Odor purposes Amber, Vanilla, Woody
Flavoring purposes Smoke

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 36 - Wear suitable protective clothing.
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:
oral-rat LD50 > 2000 mg/kg
(Dufour, 1994)

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 vanillyl ethyl ether usage levels up to:
0.6000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 20.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 22.00 (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: 17. Update in publication number(s): 22
Click here to view publication 17
average usual ppmaverage maximum ppm
baked goods: 5.0000015.00000
beverages(nonalcoholic): 30.00000300.00000
beverages(alcoholic): 30.00000300.00000
breakfast cereal: 5.0000010.00000
cheese: --
chewing gum: 200.00000600.00000
condiments / relishes: --
confectionery froastings: 100.00000500.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 3.000005.00000
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 100.00000500.00000
imitation dairy: --
instant coffee / tea: 3.0000010.00000
jams / jellies: --
meat products: --
milk products: 20.00000200.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: 50.00000500.00000
soft candy: 100.00000500.00000
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) on a request from the Commission related to Flavouring Group Evaluation 20 (FGE.20): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical group 23
View page or View pdf

Flavouring Group Evaluation 52 (FGE.52): Consideration of hydroxy- and alkoxy-substituted benzyl derivatives evaluated by JECFA (57th meeting) structurally related to benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters evaluated by EFSA in FGE.20 (2005) (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 20, Revision 1 (FGE.20Rev1): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters from chemical group 23
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 20, Revision 2 (FGE.20Rev2): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 20, Revision 3(FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :61586
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-(ethoxymethyl)-2-methoxyphenol
Chemidplus:0013184866