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Showing Compound 4-Methoxybenzoic acid (FDB010587)

Record Information
Version1.0
Creation date2010-04-08 22:09:12 UTC
Update date2019-11-26 03:03:51 UTC
Primary IDFDB010587
Secondary Accession Numbers
  • FDB008969
Chemical Information
FooDB Name4-Methoxybenzoic acid
DescriptionFlavouring agent. Food additive listed in the EAFUS Food Additive Database (Jan. 2001) 4-Methoxybenzoic acid, or anisic acid, is an organic compound which is a carboxylic acid found naturally in anise. It is a white crystalline solid which is insoluble in water and soluble in alcohols, ether, and ethyl acetate.; Anisic acid is a phenolic acid, an organic molecule commonly found in anis-seed, a common food spice. Anisic acid is occasionally found in human biofluids. Anisic acid has been characterized as a classical non-competitive inhibitor of the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA), and the hydroxylation of L-tyrosine catalyzed by tyrosinase (EC 1.14.18.1). Additionally, anisic acid is a metabolite of aniracetam, a cognition enhancer. (PMID: 14577637, 6480763, 6511847, 11597608)
CAS Number100-09-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility2 g/LALOGPS
logP1.63ALOGPS
logP1.47ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.37ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.78 m³·mol⁻¹ChemAxon
Polarizability14.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O3
IUPAC name4-methoxybenzoic acid
InChI IdentifierInChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyZEYHEAKUIGZSGI-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C(O)=O
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
Classification
Description Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • P-methoxybenzoic acid or derivatives
  • Benzoic acid
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAnisic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-3900000000-37a76df2abc65593a12fSpectrum
GC-MSAnisic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-9700000000-a7c8d60e07932915543cSpectrum
GC-MSAnisic acid, non-derivatized, GC-MS Spectrumsplash10-05n0-1920000000-e13ac77efe224f99116cSpectrum
GC-MSAnisic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-3900000000-37a76df2abc65593a12fSpectrum
GC-MSAnisic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-9700000000-a7c8d60e07932915543cSpectrum
GC-MSAnisic acid, non-derivatized, GC-MS Spectrumsplash10-05n0-1920000000-e13ac77efe224f99116cSpectrum
Predicted GC-MSAnisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pc0-3900000000-39873d2b062e65c81fedSpectrum
Predicted GC-MSAnisic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g0-9730000000-c4e338b3722c56f03a78Spectrum
Predicted GC-MSAnisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0pb9-0900000000-e12fd27c6bd5db5e22792012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0a041f6a0f7956c7a3b62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-6bad7ffd64345511fe822012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-0udr-3900000000-47cdda0bd47b983d915c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-2900000000-914fa5e9764ecaca52be2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-8900000000-ff833ddec488108721352012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-73a2bb654df643c390082012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-79c889c668d83b8931772012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-a33773d623f5deb358bd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-914fa5e9764ecaca52be2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-8900000000-cdf1618ff93a8a9e54a22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-73a2bb654df643c390082017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-79c889c668d83b8931772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-a33773d623f5deb358bd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-5900000000-363567f758c8c83ac30b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-b47c0af75d7db614046a2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-95e733af07ea3a610eb72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-04d40a78d70a72b47e732016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9600000000-b76949cb30a21d1afd242016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-9d87f412fc1d8edfb6dc2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-b0b312814568ad1a089c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9500000000-2d96be3fb0e31d3a6f732016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-df1626fb55c07fc9a9a42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-d22d130da7710d8983282021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0nor-9000000000-217f416ce9c5874adb572021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID10181338
ChEMBL IDCHEMBL21932
KEGG Compound IDC02519
Pubchem Compound ID7478
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID425
DrugBank IDDB02795
HMDB IDHMDB01101
CRC / DFC (Dictionary of Food Compounds) IDFFR17-A:FFR17-A
EAFUS ID2206
Dr. Duke ID4-METHOXYBENZOIC-ACID|P-ANISIC-ACID
BIGG IDNot Available
KNApSAcK IDC00029536
HET IDANN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1031871
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).