Record Information
Version1.0
Creation date2010-04-08 22:09:12 UTC
Update date2015-10-09 22:33:14 UTC
Primary IDFDB010587
Secondary Accession NumbersNot Available
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 Number1335-08-6
Structure
Thumb
Synonyms
SynonymSource
4-AnisateGenerator
4-Anisic acidChEBI
4-MethoxybenzoateGenerator
AnisateGenerator
Anisic acidChEBI
Badianic aciddb_source
DraconateGenerator
Draconic acidChEBI
Dragonic aciddb_source
FEMA 3945db_source
P-AnisateGenerator
P-Anisic acidChEBI
p-Anisic acid, 8CIdb_source
P-MethoxybenzoateGenerator
P-Methoxybenzoic acidChEBI
Umbellinic aciddb_source
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 KeyInChIKey=ZEYHEAKUIGZSGI-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C(O)=O
Average Molecular Weight152
Monoisotopic Molecular Weight152
Classification
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 63.15%; H 5.30%; O 31.55%DFC
Melting PointMp 184°DFC
Boiling PointBp 275-280°DFC
Experimental Water Solubility0.53 mg/mL at 37 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.96HANSCH,C ET AL. (1995)
Experimental pKapKa 4.5 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udr-3900000000-37a76df2abc65593a12fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udr-9700000000-a7c8d60e07932915543cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05n0-1920000000-e13ac77efe224f99116cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pc0-3900000000-39873d2b062e65c81fedView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9730000000-c4e338b3722c56f03a78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0pb9-0900000000-e12fd27c6bd5db5e2279View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0a041f6a0f7956c7a3b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-6bad7ffd64345511fe82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-0udr-3900000000-47cdda0bd47b983d915cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-2900000000-914fa5e9764ecaca52beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-8900000000-ff833ddec48810872135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-73a2bb654df643c39008View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-79c889c668d83b893177View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-a33773d623f5deb358bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-914fa5e9764ecaca52beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-8900000000-cdf1618ff93a8a9e54a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-73a2bb654df643c39008View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-79c889c668d83b893177View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-a33773d623f5deb358bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-95e733af07ea3a610eb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-04d40a78d70a72b47e73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9600000000-b76949cb30a21d1afd24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-9d87f412fc1d8edfb6dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-b0b312814568ad1a089cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9500000000-2d96be3fb0e31d3a6f73View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
putrid
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cadaverous
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).