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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:30 UTC
Update Date2022-03-07 02:53:13 UTC
HMDB IDHMDB0032056
Secondary Accession Numbers
  • HMDB32056
Metabolite Identification
Common NameEugenyl benzoate
DescriptionEugenyl benzoate belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Eugenyl benzoate is a mild, balsam, and clove tasting compound. Eugenyl benzoate has been detected, but not quantified in, herbs and spices. This could make eugenyl benzoate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Eugenyl benzoate.
Structure
Data?1563862213
Synonyms
ValueSource
Eugenyl benzoic acidGenerator
2-Methoxy-4-(2-propenyl)phenyl benzoateHMDB
4-Allyl-2-methoxyphenyl benzoateHMDB
Benzoyl eugenolHMDB
Eugenol benzoateHMDB
FEMA 2471HMDB
P-Eugenol, benzoateHMDB
Phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-benzoateHMDB
Phenol, 2-methoxy-4-(2-propenyl)-, benzoateHMDB
Phenol, 4-allyl-2-methoxy-, benzoateHMDB
Phenol, 4-allyl-2-methoxy-, benzoate (8ci)HMDB
2-Methoxy-4-(prop-2-en-1-yl)phenyl benzoic acidGenerator
Chemical FormulaC17H16O3
Average Molecular Weight268.3071
Monoisotopic Molecular Weight268.109944378
IUPAC Name2-methoxy-4-(prop-2-en-1-yl)phenyl benzoate
Traditional Name2-methoxy-4-(prop-2-en-1-yl)phenyl benzoate
CAS Registry Number531-26-0
SMILES
COC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C1
InChI Identifier
InChI=1S/C17H16O3/c1-3-7-13-10-11-15(16(12-13)19-2)20-17(18)14-8-5-4-6-9-14/h3-6,8-12H,1,7H2,2H3
InChI KeyZOGNBLKDKPCKGB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depside backbone
  • Benzoate ester
  • Phenol ester
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point69 - 70 °CNot Available
Boiling Point360.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.58 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.447 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0041 g/LALOGPS
logP4.23ALOGPS
logP4.58ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.61 m³·mol⁻¹ChemAxon
Polarizability29.26 ųChemAxon
Number of Rings2ChemAxon
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]+164.18531661259
DarkChem[M-H]-162.93431661259
DeepCCS[M+H]+166.23230932474
DeepCCS[M-H]-163.87430932474
DeepCCS[M-2H]-196.76130932474
DeepCCS[M+Na]+172.32630932474
AllCCS[M+H]+162.932859911
AllCCS[M+H-H2O]+159.132859911
AllCCS[M+NH4]+166.332859911
AllCCS[M+Na]+167.332859911
AllCCS[M-H]-166.332859911
AllCCS[M+Na-2H]-165.632859911
AllCCS[M+HCOO]-165.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Eugenyl benzoateCOC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C13066.9Standard polar33892256
Eugenyl benzoateCOC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C12119.5Standard non polar33892256
Eugenyl benzoateCOC1=C(OC(=O)C2=CC=CC=C2)C=CC(CC=C)=C12121.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Eugenyl benzoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0900000000-d69280ec09128f0ae4f32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eugenyl benzoate 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 - Eugenyl benzoate LC-ESI-qTof , Positive-QTOFsplash10-0006-0941000000-3bd383b4c3be332361cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenyl benzoate , positive-QTOFsplash10-0a4i-0911100000-5e96ef5e13b39ac5730f2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 10V, Positive-QTOFsplash10-014i-0690000000-d544ea9ffaa7aa0449f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 20V, Positive-QTOFsplash10-0aos-1930000000-417994551e57ef8ea0342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 40V, Positive-QTOFsplash10-0a4i-5900000000-33419990d4f460192cb52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 10V, Negative-QTOFsplash10-014i-0390000000-87b4f06ae0bdda655f172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 20V, Negative-QTOFsplash10-01di-3980000000-9a5971c7935a72d31ca62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 40V, Negative-QTOFsplash10-0fi1-5900000000-1064b308bea8bea674922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 10V, Negative-QTOFsplash10-014i-0090000000-eb5ab50d4e4aa7151b602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 20V, Negative-QTOFsplash10-0gb9-1390000000-ccd338fef71217893faf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 40V, Negative-QTOFsplash10-00fr-7910000000-3d0f78c588c415fa48ba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 10V, Positive-QTOFsplash10-00kf-0390000000-ebfaedbdd626a23e0eae2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 20V, Positive-QTOFsplash10-0a4i-1930000000-41a88c4e97ce81a358162021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenyl benzoate 40V, Positive-QTOFsplash10-0kxr-9700000000-3f5edd073f61a21886822021-09-24Wishart 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 IDNot Available
FooDB IDFDB008763
KNApSAcK IDC00053971
Chemspider ID56151
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62362
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1023511
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.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Eugenyl benzoate → Eugenoldetails