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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:44:29 UTC
Update Date2022-03-07 02:53:55 UTC
HMDB IDHMDB0033967
Secondary Accession Numbers
  • HMDB33967
Metabolite Identification
Common NameEthyl benzoate
DescriptionEthyl benzoate, also known as benzoic ether or fema 2422, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Ethyl benzoate is the ester formed by the condensation of benzoic acid and ethanol. It is a component of some artificial fruit flavors. It is a colorless liquid that is almost insoluble in water, but miscible with most organic solvents. As with many volatile esters, ethyl benzoate has a pleasant odor. Ethyl benzoate is a sweet, anise, and balsam tasting compound. Ethyl benzoate has been detected, but not quantified, in several different foods, such as black elderberries, pomes, alcoholic beverages, allspices, and blackcurrants. It has also been found in various fruits, e.g. apple, banana, sweet cherryand is also present in milk, butter, wines, black tea, bourbon vanilla and fruit brandies. Ethyl benzoate is a potentially toxic compound. ;
Structure
Data?1563862488
Synonyms
ValueSource
Benzoic acid ethyl esterChEBI
Benzoic acid, ethyl esterChEBI
Benzoic etherChEBI
Benzoyl ethyl etherChEBI
Ethyl benzenecarboxylateChEBI
Benzoate ethyl esterGenerator
Benzoate, ethyl esterGenerator
Ethyl benzenecarboxylic acidGenerator
Ethyl benzoic acidGenerator
2,4-Dihydroxy-6-methylbenzoateHMDB
2,4-Dihydroxy-6-methylbenzoic acidHMDB
2-Methoxy-1-phenyl-ethanoneHMDB
4,6-Dihydroxy-O-toluic acidHMDB
Benzoic acid, C12-13-alkyl estersHMDB
Benzoic acid, C14-15-alkyl estersHMDB
Benzoic acid, C9-11-alkyl estersHMDB
Benzoic acid,ethyl esterHMDB
Ethylester kyseliny benzooveHMDB
FEMA 2422HMDB
O-Orsellinic acidHMDB
OrsellinateHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Nameethyl benzoate
Traditional Nameethyl benzoate
CAS Registry Number93-89-0
SMILES
CCOC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c1-2-11-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3
InChI KeyMTZQAGJQAFMTAQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Benzoyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-34 °CNot Available
Boiling Point75.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.72 mg/mL at 25 °CNot Available
LogP2.64Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.83 g/LALOGPS
logP2.39ALOGPS
logP2.33ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.83 m³·mol⁻¹ChemAxon
Polarizability16.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.58931661259
DarkChem[M-H]-130.35831661259
DeepCCS[M+H]+131.68430932474
DeepCCS[M-H]-127.85330932474
DeepCCS[M-2H]-165.28930932474
DeepCCS[M+Na]+140.75630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl benzoateCCOC(=O)C1=CC=CC=C11778.2Standard polar33892256
Ethyl benzoateCCOC(=O)C1=CC=CC=C11151.2Standard non polar33892256
Ethyl benzoateCCOC(=O)C1=CC=CC=C11207.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-2900000000-37faa5967536e1c37df12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a6r-5900000000-c9d5dba851f474dd94562017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-5900000000-240d67885345369282f32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-6900000000-5b05b2c2170f6252ca9a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-1900000000-4dfdb3091a0b0e276d972017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate CI-B (Non-derivatized)splash10-0ab9-2900000000-642cce491cf1fc2d77842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0pdi-7900000000-da9006b983d81f0771962017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0pdi-8900000000-44a1b5b320f6a221cb8a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-1900000000-f9719df41d062495f6502017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-2900000000-37faa5967536e1c37df12018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a6r-5900000000-c9d5dba851f474dd94562018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-5900000000-240d67885345369282f32018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-6900000000-5b05b2c2170f6252ca9a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-1900000000-4dfdb3091a0b0e276d972018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate CI-B (Non-derivatized)splash10-0ab9-2900000000-642cce491cf1fc2d77842018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0pdi-7900000000-da9006b983d81f0771962018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0pdi-8900000000-44a1b5b320f6a221cb8a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl benzoate EI-B (Non-derivatized)splash10-0a4i-1900000000-f9719df41d062495f6502018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl benzoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3900000000-5e6280da53233e98e4152016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl benzoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-4900000000-b14d01178eaee5ec18d32014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 10V, Positive-QTOFsplash10-0udi-0900000000-86368d5a557887feaf322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 20V, Positive-QTOFsplash10-0pb9-1900000000-b8ded68691c400a7c3ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 40V, Positive-QTOFsplash10-0a4i-8900000000-58fb24e660c8d2bff1892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 10V, Negative-QTOFsplash10-0002-1900000000-ddca82f0ff01b64c98d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 20V, Negative-QTOFsplash10-0f92-3900000000-dab9271d0d827cbe329c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 40V, Negative-QTOFsplash10-004i-9400000000-36b3029eb6eec5567af52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 10V, Negative-QTOFsplash10-0002-1900000000-20bd5ddcafdc7ff644b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 20V, Negative-QTOFsplash10-004i-9400000000-d120db94c385cdc932752021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 40V, Negative-QTOFsplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 10V, Positive-QTOFsplash10-0ab9-2900000000-345e7e905026a0d866d62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 20V, Positive-QTOFsplash10-0a6r-5900000000-e1fcea40403e16c81fc02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl benzoate 40V, Positive-QTOFsplash10-0a6r-8900000000-8279275c91418beaccbe2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDFDB012197
KNApSAcK IDC00053157
Chemspider ID6897
KEGG Compound IDC01839
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl_benzoate
METLIN IDNot Available
PubChem Compound7165
PDB IDNot Available
ChEBI ID156074
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1154981
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .