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    General Material Information
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    PhysChem Properties
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    Organoleptic Properties
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eugenyl acetate

Chemical Structure

General Material Information

Preferred name eugenyl acetate
Trivial Name Eugenyl acetate
Short Description acetyl eugenol
Formula C12 H14 O3
CAS Number 93-28-7
FEMA Number 2469
Flavis Number 9.02
ECHA Number 202-235-6
FDA UNII V9OSB376X8
Nikkaji Number J34.551B
Beilstein Number 1964745
MDL MFCD00026191
COE Number 210
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1531 eugenyl acetate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 93-28-7 ; EUGENYL ACETATE
Synonyms
  • acetic acid 4-allyl-2-methoxy-phenyl ester
  • acetic acid eugenyl ester
  • 1-acetoxy-2-methoxy-4-allyl benzene
  • 1-acetoxy-2-methoxy-4-allylbenzene
  • acetyl eugenol
  • 4-allyl-2-methoxyphenol acetate
  • 4-allyl-2-methoxyphenyl acetate
  • 4-allyl-2-methoxyphenylacetat
  • eugenol acetate
  • 1,3,4-eugenol acetate
  • eugenyl acetate FCC
  • eugenyle acetate
  • 2-methoxy-4-(2-propen-1-yl) phenyl acetate
  • 2-methoxy-4-(2-propen-1-yl)phenyl acetate
  • 2-methoxy-4-(2-propenyl) phenyl acetate
  • 2-methoxy-4-(2-propenyl)phenol acetate
  • 2-methoxy-4-(2-propenyl)phenyl acetate
  • 2-methoxy-4-(prop-2-en-1-yl)phenyl acetate
  • 2-methoxy-4-prop-2-enylphenyl acetate
  • (2-methoxy-4-prop-2-enylphenyl) acetate
  • 2-methoxy-4,2-propen-1-yl phenyl acetate
  • phenol, 2-methoxy-4-(2-propenyl)-, acetate
  • phenol, 2-methoxy-4-(2-propen-1-yl)-, acetate
  • phenol, 2-methoxy-4-(2-propenyl)-, acetate
  • phenol, 4-allyl-2-methoxy-, acetate
  • 4-(2-propenyl)-2-methoxyphenyl ethanoate
  • (2-methoxy-4-prop-2-enylphenyl) acetate
  • Phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-acetate
  • Aceteugenol
  • Acetyleugenol
  • 4-Allyl-2-methoxyphenyl acetate
  • O-Acetyleugenol
  • NSC 1242
  • 2-Methoxy-4-(2-propenyl)phenol acetate
  • 2-Methoxy-4-(prop-2-en-1-yl)phenyl acetate

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

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Literature & References

(2-methoxy-4-prop-2-enylphenyl) acetate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:93-28-7
Pubchem (cid):7136
Pubchem (sid):134972842
Pherobase:View
Publications by Info
eugenol and related hydroxyallylbenzene derivatives
Publications by PubMed
Ultrasound-assisted extraction and quantitation of oils from Syzygium aromaticum flower bud (clove) with supercritical carbon dioxide.
Apoptosis-like death in Leishmania donovani promastigotes induced by eugenol-rich oil of Syzygium aromaticum.
Structure-activity relationships of monoterpenes and acetyl derivatives against Aedes aegypti (Diptera: Culicidae) larvae.
In vitro inhibitory effect of clove essential oil and its two active principles on tooth decalcification by apple juice.
Chemical variability in the essential oil of Cinnamomum tamala L. leaves from India.
Acaricidal activity of eugenol based compounds against scabies mites.
Efficacy of chemically characterized Piper betle L. essential oil against fungal and aflatoxin contamination of some edible commodities and its antioxidant activity.
Study of the aerosol fragrances of eugenol derivatives in Cananga odorata using diffuse reflectance infrared Fourier transform spectroscopy and gas chromatography.
The effect of clove oil on the transdermal delivery of ibuprofen in the rabbit by in vitro and in vivo methods.
Antioxidant properties of the essential oil of Eugenia caryophyllata and its antifungal activity against a large number of clinical Candida species.
Chemical composition and antioxidant properties of clove leaf essential oil.
Chemical composition and in vitro antimicrobial activities of the essential oils from endemic Psiadia species growing in mauritius.
Ovicidal and adulticidal effects of Eugenia caryophyllata bud and leaf oil compounds on Pediculus capitis.
Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
Veratryl alcohol-mediated oxidation of isoeugenyl acetate by lignin peroxidase.
Antiplatelet principles from a food spice clove (Syzygium aromaticum L) [corrected].

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):C14567
HMDB (The Human Metabolome Database):HMDB34122
FooDB:FDB012393
Export Tariff Code:2915.39.3500
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 206.24118041992
Specific gravity @ 25 °C
Pounds per Gallon 8.962 to 9.003
Specific gravity @ 20 °C
Pounds per Gallon 8.956 to 9.022
Refractive Index 1.516 to 1.52 @ 20 °C
Melting Point 24 to 27°C @ 760 mm Hg
Boiling Point 281 to 285°C @ 760 mm Hg
Acid Value 1 max KOH/g
Vapor Pressure 0.008 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 2.71 est
Solubility
alcohol Yes
essential oils Yes
paraffin oil Yes
water, 98.28 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Spicy
fresh, sweet, woody, clove, floral, carnation, malty, spicy
Odor strength medium
Substantivity 400 hour(s) at 100.00 %
Luebke, William tgsc, (1996) At 100.00 %. fresh sweet woody clove floral carnation malt spice
Flavor Type: Spicy
spicy, clove, allspice, carnation
Luebke, William tgsc, (1996) Spicy warm clove allspice sweet carnation
General comment Sweet aromatic, spicy-estery

Occurrences

Potential Uses

Applications
Odor purposes Acacia, Acorn, Allspice, Allspice, Amber, Ambreine, Ambrette oil replacer, Animal, Arnica flower, Autumn, Azalea, Balsam, Bay rum, Bayberry, Benzoin absolute replacer, Bread baked bread, Cabreuva wood, Calamus oil replacer, Carnation, Cassia, Cassia blossom, Castoreum, Chamomile, Champaca, Cherry black cherry, Chestnut blossom, Cinnamon, Citrus, Clove, Clove blossom, Coconut, Coconut tropical coconut, Coffee, Copaiba balsam, Coronilla, Croton eluteria bark, Currant, Cypress oil replacer, Dahlia, Daisy, Daphne, Date, Deertongue absolute replacer, Dogwood, Elder flower, Fagonia, Fenugreek, Fern, Fig, Fir balsam, Floral, Flouve, Flouve blossom, Forest, Genet, Gingerbread, Graham cracker, Green grass, Guaiacwood, Habuba, Hawthorn, Hay new mown hay, Heather, Hollyberry, Hugonia, Immortelle, Incense, Iris blossom, Jasmin, Juniper berry, Kewda, Labdanum, Leather, Lovage root, Maja, Malt, Moss, Mulberry, Musk, Narcissus, Nutmeg, Oakwood, Opoponax, Oriental, Osmanthus, Patchouli, Petunia, Plum, Powder, Pumpkin pie, Rose, Rose d'orient, Rose moss rose, Rose white rose, Saffron, Sandalwood, Scented stock, Spice, Spicewood, Strawberry, Sweet grass, Tobacco, Tonka bean, Tulip, Valerian, Vanilla, Wisteria, Woodruff, Woody, Yerba mate
Flavoring purposes Absinthe, Benzoin absolute replacer, Cake, Cappuccino, Capsicum, Caramel, Chicory root, Chocolate cacao, Cookie, Copaiba balsam, Croton eluteria bark, Fenugreek, Guaiacwood, Immortelle, Lovage root, Milk malted milk, Valerian, Yerba mate
Other purposes Blossom tropical blossom, Fantasy blends, Fixer, Liverwort, Straw, Timber, Weedy
Cosmetic purposes Fragrance

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 38 - Irritating to 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 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.
Human Experience:
20 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 1670 mg/kg
SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

intratracheal-rat LDLo 48 mg/kg
LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI
Archives of Toxicology. Vol. 59, Pg. 78, 1986.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 12, Pg. 877, 1974.

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 eugenyl acetate usage levels up to:
8.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 19.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 90.00 (μg/capita/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
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: -10.00000
beverages(nonalcoholic): -0.43000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: 25.00000100.00000
condiments / relishes: 2.000002.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -3.30000
fruit ices: -3.30000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -20.00000
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):

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 the safety and efficacy of allylhydroxybenzenes (chemical group 18) when used as flavourings 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):93-28-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7136
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(2-methoxy-4-prop-2-enylphenyl) acetate
Chemidplus:0000093287
RTECS:SJ4550000 for cas# 93-28-7