Showing Compound Card for Eugenyl acetate (CDB000606)

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Record Information
Version1.0
Created at2020-03-19 00:46:18 UTC
Updated at2020-12-07 19:07:34 UTC
CannabisDB IDCDB000606
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEugenyl acetate
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. Eugenyl acetate has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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, MeSH
Eugenol acetateHMDB
Eugenyl acetateHMDB, MeSH
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
Chemical FormulaC12H14O3
Average Molecular Weight206.24
Monoisotopic Molecular Weight206.0943
IUPAC Name2-methoxy-4-(prop-2-en-1-yl)phenyl acetate
Traditional Nameeugenyl acetate
CAS Registry Number93-28-7
SMILES
COC1=C(OC(C)=O)C=CC(CC=C)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point30 - 31 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSEugenyl acetate, non-derivatized, GC-MS Spectrumsplash10-03dl-5900000000-07dccf5db214bbe5da36Spectrum
GC-MSEugenyl acetate, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-9c3ff0de59c85e8294b0Spectrum
GC-MSEugenyl acetate, non-derivatized, GC-MS Spectrumsplash10-03di-4900000000-67c6396f6b356ed19199Spectrum
GC-MSEugenyl acetate, non-derivatized, GC-MS Spectrumsplash10-03dl-5900000000-07dccf5db214bbe5da36Spectrum
GC-MSEugenyl acetate, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-9c3ff0de59c85e8294b0Spectrum
GC-MSEugenyl acetate, non-derivatized, GC-MS Spectrumsplash10-03di-4900000000-67c6396f6b356ed19199Spectrum
Predicted GC-MSEugenyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-4900000000-a304eb063db0dbfb4754Spectrum
Predicted GC-MSEugenyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0190000000-aac08a05e91542bc8ee62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0a4i-0490000000-7b507551acbb774fdb392020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4r-0970000000-103298343d2eeedb4b712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-052r-0930000000-790979ed2c402e55985f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-052r-0920000000-fca2cfe497d7997a05d92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-052r-0910000000-85b083c7cb397c23ae7d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-052r-0900000000-cd22b7ee4e8289af04cd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-059i-0900000000-bffea5112bca02611ffb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-05br-0900000000-b4fc4d81a5f5db11ba7d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-05dr-0900000000-9c4086a215cced0aaebc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00bi-0900000000-d5a5b0376c1d44d532692020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-004i-1900000000-fa5b9e1fa96c52be882a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-004i-3900000000-cf5ef9e2fee8299440e92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-004l-5900000000-e7818cc62a6d1f999ef82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0fvi-9700000000-096c27413dd813f427c82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-000i-0900000000-34fbb1b55cebae7182b32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-004i-0900000000-73ec60ea1131e1a259372020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-000i-0900000000-af68f4a566c5bf7574cb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-0a4i-4900000000-cd4aeb3ab174f068fb152020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-00di-0900000000-3742e23de9fd8aace9482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-0a4j-0900000000-9720dfd149796e13f6072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-000i-0900000000-a327ab73af988d78e2682020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000i-0900000000-5a75ad949f6ef3df602a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-000i-0900000000-b0b4702efee1e33224282020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0079-0900000000-7ecf1428cf5a2ae600b52020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034122
DrugBank IDNot Available
Phenol Explorer Compound ID647
FoodDB IDFDB012393
KNApSAcK IDC00053972
Chemspider ID6869
KEGG Compound IDC14567
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7136
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]