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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2021-09-07 16:45:32 UTC
HMDB IDHMDB0002072
Secondary Accession Numbers
  • HMDB02072
Metabolite Identification
Common Name4-Methoxyphenylacetic acid
Description4-methoxyphenylacetic acid is a monocarboxylic acid that is phenylacetic acid carrying a 4-methoxy substituent. It is used as an intermediate for pharmaceuticals and other organic synthesis. It has been found to inhibit the germination of cress and lettuce seeds. It has a role as a plant metabolite, a plant growth retardant and an Aspergillus metabolite. It is a monocarboxylic acid and a monomethoxybenzene. 4-Methoxyphenylacetic acid, also known as 4-methoxybenzeneacetate or 2-(p-anisyl)acetic acid, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 4-Methoxyphenylacetic acid is a 4-O-Methylated catecholamine metabolite found in normal human urine, cerebrospinal fluid and brain tissue.
Structure
Data?1582752227
Synonyms
ValueSource
(4-Methoxyphenyl)acetic acidChEBI
(p-Methoxyphenyl)acetic acidChEBI
2-(p-Anisyl)acetic acidChEBI
4-Methoxybenzeneacetic acidChEBI
Homoanisic acidChEBI
p-Methoxy-alpha-toluic acidChEBI
p-Methoxyphenylacetic acidChEBI
(4-Methoxyphenyl)acetateGenerator
(p-Methoxyphenyl)acetateGenerator
2-(p-Anisyl)acetateGenerator
4-MethoxybenzeneacetateGenerator
HomoanisateGenerator
p-Methoxy-a-toluateGenerator
p-Methoxy-a-toluic acidGenerator
p-Methoxy-alpha-toluateGenerator
p-Methoxy-α-toluateGenerator
p-Methoxy-α-toluic acidGenerator
p-MethoxyphenylacetateGenerator
4-MethoxyphenylacetateGenerator
3-Methoxyphenylacetic acid, potassium saltMeSH
3-Methoxyphenylacetic acidMeSH
(4-Methoxy-phenyl)-acetateHMDB
(4-Methoxy-phenyl)-acetic acidHMDB
4-Methoxy phenylacetic acidHMDB
4-Methoxy-benzeneacetateHMDB
4-Methoxy-benzeneacetic acidHMDB
homo-P-Anisic acidHMDB
P-Methoxyphenyl-acetateHMDB
P-Methoxyphenyl-acetic acidHMDB
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-(4-methoxyphenyl)acetic acid
Traditional Name4-methoxyphenylacetic acid
CAS Registry Number104-01-8
SMILES
COC1=CC=C(CC(O)=O)C=C1
InChI Identifier
InChI=1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
InChI KeyNRPFNQUDKRYCNX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point87 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18 mg/mLNot Available
LogP1.42HANSCH,C ET AL. (1995)
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.43 g/LALOGPS
logP1.73ALOGPS
logP1.45ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.83 m³·mol⁻¹ChemAxon
Polarizability16.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M+H]+ExperimentalMetCCS_train_pos137.4430932474
AllCCS[M+H]+ExperimentalNot Available137.951http://allccs.zhulab.cn/database/detail?ID=AllCCS00000528
DarkChem[M+H]+PredictedNot Available137.75631661259
DarkChem[M-H]-PredictedNot Available136.59231661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4-Methoxyphenylacetic acid,1TMS,#11555.4685https://arxiv.org/abs/1905.12712
4-Methoxyphenylacetic acid,1TBDMS,#11769.6365https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1900000000-3f38b31d62021162fa792017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1900000000-3f38b31d62021162fa792018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4900000000-c0ac9a8c960efa14aa9e2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9610000000-827c52ec2601e1848c832017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-4900000000-c0ac9a8c960efa14aa9e2021-09-05View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-9a07510e862a3a8fbc0f2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-4900000000-a51b42c5bcf30f73fa212012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-09ddc34c57dd8f759d362012-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-dd75ebae080e8172f70b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0900000000-484c747c20eb441a0e702017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9500000000-41ce119cf280dbf7526d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-0f38d32c191cd9ba89322017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06dj-0900000000-b2cf5d48884871a755b12017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-55e9339f98026f5943d32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-1b3f50229a3d0ec9c0bc2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-2900000000-a9f561b97c1d5a1e63112021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-b841e9a4caa432e86a172021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-0900000000-68e12f60465e411079c32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3900000000-0b3e0467ba9195464cf32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-6f175172d619e7e483742021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.123 +/- 0.032 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.107 +/- 0.035 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.113 +/- 0.029 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.175 +/- 0.066 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.126 +/- 0.029 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.114 +/- 0.012 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.111 +/- 0.03 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.445 +/- 0.382 uMAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.073 +/- 0.046 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral squamous cell carcinoma (OSCC) details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral leukoplakia (OLK) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022832
KNApSAcK IDNot Available
Chemspider ID7406
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6472
PubChem Compound7690
PDB IDNot Available
ChEBI ID55501
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]