Record Information
Version1.0
Creation date2010-04-08 22:08:21 UTC
Update date2020-04-21 18:02:13 UTC
Primary IDFDB008969
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAnisic acid
DescriptionP-anisic acid, also known as 4-methoxybenzoic acid or anisate, belongs to P-methoxybenzoic acids and derivatives class of compounds. Those are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. P-anisic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). P-anisic acid can be synthesized from benzoic acid. P-anisic acid can also be synthesized into methyl p-anisate. P-anisic acid is a faint, sweet, and cadaverous tasting compound found in anise, cocoa bean, fennel, and german camomile, which makes P-anisic acid a potential biomarker for the consumption of these food products. P-anisic acid can be found primarily in feces. P-anisic acid exists in all eukaryotes, ranging from yeast to humans.
CAS Number1335-08-6
Structure
Thumb
Synonyms
SynonymSource
4-Anisic acidChEBI
Anisic acidChEBI
Draconic acidChEBI
p-Methoxybenzoic acidChEBI
4-Methoxybenzoic acidKegg
4-AnisateGenerator
AnisateGenerator
DraconateGenerator
p-MethoxybenzoateGenerator
4-MethoxybenzoateGenerator
p-AnisateGenerator
4-Anisic acid, copper (+2) saltHMDB
4-Anisic acid, 14C-carboxyHMDB
4-Anisic acid, potassium saltHMDB
4-Anisic acid, sodium saltHMDB
Para-anisic acidHMDB
p-Anisic acidChEBI
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point185 oC
Boiling PointNot Available
Experimental Water Solubility90 mg/mL at 140 oCSEIDELL,A (1941)
Experimental logP1.96HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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-e12fd27c6bd5db5e2279Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0a041f6a0f7956c7a3b6Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-6bad7ffd64345511fe82Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-0udr-3900000000-47cdda0bd47b983d915cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-2900000000-914fa5e9764ecaca52beSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-8900000000-ff833ddec48810872135Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-73a2bb654df643c39008Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4l-9000000000-79c889c668d83b893177Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-a33773d623f5deb358bdSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-914fa5e9764ecaca52beSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-8900000000-cdf1618ff93a8a9e54a2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-73a2bb654df643c39008Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-79c889c668d83b893177Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-a33773d623f5deb358bdSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-5900000000-363567f758c8c83ac30bSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-b47c0af75d7db614046aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-95e733af07ea3a610eb7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-04d40a78d70a72b47e73Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9600000000-b76949cb30a21d1afd24Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-9d87f412fc1d8edfb6dcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0900000000-b0b312814568ad1a089cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9500000000-2d96be3fb0e31d3a6f73Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-df1626fb55c07fc9a9a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-d22d130da7710d898328Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0nor-9000000000-217f416ce9c5874adb57Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID231
Dr. Duke IDANISIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti rheumatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti salmonella33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).