Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2020-09-17 15:35:09 UTC
Primary IDFDB012393
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAceteugenol
DescriptionEugenyl acetate, also known as acetyleugenol, is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. Eugenyl acetate is constituted by a benzene ring, substituted by a methoxy group acetoxy group in position 1, a methoxy group in position 2 and a propenoil moiety in position 4. It is the acetylated derivative of eugenol. Eugenyl acetate is a sweet, carnation, and clove tasting compound. It is found in the highest concentration in a few different foods, such as cloves, ceylon cinnamons, and sweet bay. It has also been detected, but not quantified, in nutmegs, herbs and spices, cumins, star anises, and lemon balms.
CAS Number93-28-7
Structure
Thumb
Synonyms
SynonymSource
1,3,4-Eugenol acetateHMDB
1-Acetoxy-2-methoxy-4-allylbenzeneHMDB
2-Methoxy-4-(2-propen-1-yl)phenyl acetateHMDB
2-Methoxy-4-(2-propenyl)phenyl acetateHMDB
4-Allyl-2-methoxyphenol acetateHMDB
4-Allyl-2-methoxyphenyl acetateHMDB
Aceto eugenolHMDB
Acetyl eugenolHMDB
AcetyleugenolHMDB
Eugenol acetateHMDB
Eugenyl acetateHMDB
FEMA 2469HMDB
Phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-acetateHMDB
Phenol, 2-methoxy-4-(2-propenyl)-, acetateHMDB
Phenol, 4-allyl-2-methoxy-, acetateHMDB
(2-Methoxy-4-prop-2-enylphenyl) acetateHMDB
2-Methoxy-4-(2-propenyl)phenol acetateHMDB
AceteugenolHMDB
O-AcetyleugenolHMDB
Eugenyl acetic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP3ALOGPS
logP2.52ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.94 m³·mol⁻¹ChemAxon
Polarizability22.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H14O3
IUPAC name2-methoxy-4-(prop-2-en-1-yl)phenyl acetate
InChI IdentifierInChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3
InChI KeySCCDQYPEOIRVGX-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC(C)=O)C=CC(CC=C)=C1
Average Molecular Weight206.2378
Monoisotopic Molecular Weight206.094294314
Classification
Description Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.89%; H 6.84%; O 23.27%DFC
Melting PointMp 30-31°DFC
Boiling PointBp13 163-164°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAceteugenol, non-derivatized, GC-MS Spectrumsplash10-03dl-5900000000-07dccf5db214bbe5da36Spectrum
GC-MSAceteugenol, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-9c3ff0de59c85e8294b0Spectrum
GC-MSAceteugenol, non-derivatized, GC-MS Spectrumsplash10-03di-4900000000-67c6396f6b356ed19199Spectrum
GC-MSAceteugenol, non-derivatized, GC-MS Spectrumsplash10-03dl-5900000000-07dccf5db214bbe5da36Spectrum
GC-MSAceteugenol, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-9c3ff0de59c85e8294b0Spectrum
GC-MSAceteugenol, non-derivatized, GC-MS Spectrumsplash10-03di-4900000000-67c6396f6b356ed19199Spectrum
Predicted GC-MSAceteugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-4900000000-a304eb063db0dbfb4754Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0190000000-aac08a05e91542bc8ee6Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0a4i-0490000000-7b507551acbb774fdb39Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4r-0970000000-103298343d2eeedb4b71Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-052r-0930000000-790979ed2c402e55985fSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-052r-0920000000-fca2cfe497d7997a05d9Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-052r-0910000000-85b083c7cb397c23ae7dSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-052r-0900000000-cd22b7ee4e8289af04cdSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-059i-0900000000-bffea5112bca02611ffbSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-05br-0900000000-b4fc4d81a5f5db11ba7dSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-05dr-0900000000-9c4086a215cced0aaebcSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00bi-0900000000-d5a5b0376c1d44d53269Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-004i-1900000000-fa5b9e1fa96c52be882aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-004i-3900000000-cf5ef9e2fee8299440e9Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-004l-5900000000-e7818cc62a6d1f999ef8Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0fvi-9700000000-096c27413dd813f427c8Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-000i-0900000000-34fbb1b55cebae7182b3Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-004i-0900000000-73ec60ea1131e1a25937Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-000i-0900000000-af68f4a566c5bf7574cbSpectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-0a4i-4900000000-cd4aeb3ab174f068fb15Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1970000000-078b3c4b086a815a0179Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mn-1910000000-de079e69f30f2740b838Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ke-8900000000-144bb0f796b3acec879aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3690000000-eca8212470cdf5fac061Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bta-3920000000-934e30142781c78ac358Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-7900000000-163bde03d45c33c01397Spectrum
NMRNot Available
ChemSpider ID6869
ChEMBL IDCHEMBL108299
KEGG Compound IDC14567
Pubchem Compound ID7136
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID647
DrugBank IDNot Available
HMDB IDHMDB34122
CRC / DFC (Dictionary of Food Compounds) IDHDW90-Y:HGS52-P
EAFUS ID1327
Dr. Duke IDEUGENYL-ACETATE|ACETOEUGENOL|ACETYL-EUGENOL|EUGENOL-ACETATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1005011
SuperScent ID7136
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
anti aggregantDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti radicularDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cholagogueDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
trypsin enhancerDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
clove
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
carnation
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
malt
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).