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Showing Compound Anisic acid (FDB008969)

Record Information
Version1.0
Creation date2010-04-08 22:08:21 UTC
Update date2025-11-18 23:14:50 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
MOLSDFPDBSMILESInChI
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
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-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 IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0001101
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID231
Dr. Duke IDANISIC-ACID
BIGG IDNot Available
KNApSAcK IDC00029536
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDP-Anisic_acid
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 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-rheumatic52217 An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions.DUKE
Anti-salmonella33282 An agent that targets and eliminates Salmonella bacteria, reducing the risk of food poisoning and gastrointestinal infections. Therapeutically, it is used to treat salmonellosis, a disease caused by Salmonella infection, and to prevent outbreaks in high-risk individuals, such as those with weakened immune systems.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Tyrosinase inhibitor59997 An agent that blocks the activity of tyrosinase, an enzyme involved in melanin production, reducing skin pigmentation. Therapeutically used to treat hyperpigmentation disorders, such as melasma and vitiligo, and as a skin-lightening agent in dermatology.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).