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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:48 UTC
Update Date2021-10-13 06:25:03 UTC
HMDB IDHMDB0032617
Secondary Accession Numbers
  • HMDB32617
Metabolite Identification
Common NameMethyl phenylacetate
DescriptionMethyl phenylacetate, also known as fema 2733 or mephaneine, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Methyl phenylacetate is a sweet, almond, and floral tasting compound. Methyl phenylacetate is found, on average, in the highest concentration within corns. Methyl phenylacetate has also been detected, but not quantified, in several different foods, such as cocoa and cocoa products, coffee and coffee products, fruits, and pepper (c. frutescens). This could make methyl phenylacetate a potential biomarker for the consumption of these foods. Methyl phenylacetate has a strong odor similar to honey. It is a colorless liquid that is only slightly soluble in water, but soluble in most organic solvents. It is used in the flavor industry and in perfumes to impart honey scents. This compound also occurs in brandy, capsicum, coffee, honey, pepper, and some wine. Methyl phenyldiazoacetate, precursor to cyclopropanation agents, is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base. Methyl phenylacetate is an organic compound that is the methyl ester of phenylacetic acid, with the structural formula C6H5CH2COOCH3.
Structure
Data?1563862283
Synonyms
ValueSource
Methyl phenylacetic acidGenerator
FEMA 2733HMDB
MephaneineHMDB
Methyl alpha-toluateHMDB
Methyl ester OF phenylacetic acidHMDB
Methyl 2-phenylacetic acidGenerator
Methyl phenylacetateMeSH
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Namemethyl 2-phenylacetate
Traditional Namemethyl phenylacetate
CAS Registry Number101-41-7
SMILES
COC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
InChI KeyCRZQGDNQQAALAY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point215.00 to 217.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2072 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.83Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP10(2.03) g/LALOGPS
logP10(1.76) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.13 m³·mol⁻¹ChemAxon
Polarizability16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.77531661259
DarkChem[M-H]-131.68231661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized)splash10-0006-9200000000-389b3d6431858f4110c92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized)splash10-0006-9200000000-eeeabb5445489ab0953b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized)splash10-0006-9100000000-18e224838518b1ddae9f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized)splash10-0006-9100000000-1edd67a79f223f8276412017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized)splash10-0006-9200000000-389b3d6431858f4110c92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized)splash10-0006-9200000000-eeeabb5445489ab0953b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized)splash10-0006-9100000000-18e224838518b1ddae9f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl phenylacetate EI-B (Non-derivatized)splash10-0006-9100000000-1edd67a79f223f8276412018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl phenylacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-87bae92e5b97546941aa2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl phenylacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9200000000-52232f96c18eca1b23942015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 10V, Positive-QTOFsplash10-0gb9-0900000000-f25a76df13db20a2b4102016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 20V, Positive-QTOFsplash10-0gbc-3900000000-511b0f2135ac341e4b052016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 40V, Positive-QTOFsplash10-0006-9300000000-137ed2396b7316ce05792016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 10V, Negative-QTOFsplash10-0002-0900000000-f12b2444ec831bdb6ca92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 20V, Negative-QTOFsplash10-00kb-0900000000-714e146d401300f08a2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 40V, Negative-QTOFsplash10-014i-4900000000-d72c1c0fc3949b615eb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 10V, Negative-QTOFsplash10-0007-9800000000-5ae7754141b3f8f634c02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 20V, Negative-QTOFsplash10-00kf-9500000000-09614850d98f667a51b72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 40V, Negative-QTOFsplash10-0006-9000000000-ee5158f79753ba716d142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 10V, Positive-QTOFsplash10-0006-9600000000-ab903e003c3368a3914e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 20V, Positive-QTOFsplash10-0006-9000000000-d017d7725bdee26883d12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl phenylacetate 40V, Positive-QTOFsplash10-0006-9000000000-5190dde93ea85ed050ff2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB010559
KNApSAcK IDC00051576
Chemspider ID7278
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl phenylacetate
METLIN IDNot Available
PubChem Compound7559
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008431
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.. .