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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:55:04 UTC
Update Date2021-10-13 06:38:54 UTC
HMDB IDHMDB0034122
Secondary Accession Numbers
  • HMDB34122
Metabolite Identification
Common NameAceteugenol
DescriptionAceteugenol, also known as eugenol acetate, 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. Aceteugenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Aceteugenol is a sweet-, carnation-, and clove-tasting compound. Outside of the human body, aceteugenol is found, on average, in the highest concentration in a few different foods, such as cloves, Ceylon cinnamons, and sweet bay. Aceteugenol has also been detected, but not quantified in, several different foods, such as nutmegs, herbs and spices, cumins, star anises, and lemon balms. This could make aceteugenol a potential biomarker for the consumption of these foods. Aceteugenol is a flavouring agent found in Caraway, oil of clove (Syzygium aromaticum), cinnamon leaf (Cinnamomum verum), and other essential oils.
Structure
Data?1588714570
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 Weight206.2378
Monoisotopic Molecular Weight206.094294314
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point30 - 31 °CNot Available
Boiling Point92.67 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility109700 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.410 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP10(3) g/LALOGPS
logP10(2.52) g/LChemAxon
logS10(-3.1) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.16431661259
DarkChem[M-H]-146.25331661259
DeepCCS[M+H]+145.89430932474
DeepCCS[M-H]-143.53630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AceteugenolCOC1=C(OC(C)=O)C=CC(CC=C)=C12331.8Standard polar33892256
AceteugenolCOC1=C(OC(C)=O)C=CC(CC=C)=C11520.7Standard non polar33892256
AceteugenolCOC1=C(OC(C)=O)C=CC(CC=C)=C11548.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Aceteugenol EI-B (Non-derivatized)splash10-03dl-5900000000-07dccf5db214bbe5da362017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aceteugenol EI-B (Non-derivatized)splash10-03di-1900000000-9c3ff0de59c85e8294b02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aceteugenol EI-B (Non-derivatized)splash10-03di-4900000000-67c6396f6b356ed191992017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aceteugenol EI-B (Non-derivatized)splash10-03dl-5900000000-07dccf5db214bbe5da362018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aceteugenol EI-B (Non-derivatized)splash10-03di-1900000000-9c3ff0de59c85e8294b02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aceteugenol EI-B (Non-derivatized)splash10-03di-4900000000-67c6396f6b356ed191992018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aceteugenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-4900000000-a304eb063db0dbfb47542017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aceteugenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 1V, positive-QTOFsplash10-0a4i-0190000000-aac08a05e91542bc8ee62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 2V, positive-QTOFsplash10-0a4i-0490000000-7b507551acbb774fdb392020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 3V, positive-QTOFsplash10-0a4r-0970000000-103298343d2eeedb4b712020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 4V, positive-QTOFsplash10-052r-0930000000-790979ed2c402e55985f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 4V, positive-QTOFsplash10-052r-0920000000-fca2cfe497d7997a05d92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 5V, positive-QTOFsplash10-052r-0910000000-85b083c7cb397c23ae7d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 6V, positive-QTOFsplash10-052r-0900000000-cd22b7ee4e8289af04cd2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 7V, positive-QTOFsplash10-059i-0900000000-bffea5112bca02611ffb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 8V, positive-QTOFsplash10-05br-0900000000-b4fc4d81a5f5db11ba7d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 9V, positive-QTOFsplash10-05dr-0900000000-9c4086a215cced0aaebc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 12V, positive-QTOFsplash10-00bi-0900000000-d5a5b0376c1d44d532692020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 15V, positive-QTOFsplash10-004i-1900000000-fa5b9e1fa96c52be882a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 18V, positive-QTOFsplash10-004i-3900000000-cf5ef9e2fee8299440e92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 21V, positive-QTOFsplash10-004l-5900000000-e7818cc62a6d1f999ef82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol Orbitrap 27V, positive-QTOFsplash10-0fvi-9700000000-096c27413dd813f427c82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol n/a 14V, positive-QTOFsplash10-000i-0900000000-34fbb1b55cebae7182b32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol n/a 14V, positive-QTOFsplash10-004i-0900000000-73ec60ea1131e1a259372020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol n/a 14V, positive-QTOFsplash10-000i-0900000000-af68f4a566c5bf7574cb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Aceteugenol n/a 14V, positive-QTOFsplash10-0a4i-4900000000-cd4aeb3ab174f068fb152020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aceteugenol 10V, Positive-QTOFsplash10-0a4i-1970000000-078b3c4b086a815a01792016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aceteugenol 20V, Positive-QTOFsplash10-05mn-1910000000-de079e69f30f2740b8382016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aceteugenol 40V, Positive-QTOFsplash10-00ke-8900000000-144bb0f796b3acec879a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aceteugenol 10V, Negative-QTOFsplash10-0a4i-3690000000-eca8212470cdf5fac0612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aceteugenol 20V, Negative-QTOFsplash10-0bta-3920000000-934e30142781c78ac3582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aceteugenol 40V, Negative-QTOFsplash10-0a4m-7900000000-163bde03d45c33c013972016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID647
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1627481
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .