You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.

Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-09-11 01:33:56 UTC
NP-MRD IDNP0000013
Secondary Accession NumbersNone
Natural Product Identification
Common NameVanillic acid
DescriptionVanillic acid, also known as vanillate or acide vanillique, belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Vanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillic acid exists in all living species, ranging from bacteria to humans. Vanillic acid is a sweet, bean, and creamy tasting compound. Outside of the human body, Vanillic acid is found, on average, in the highest concentration within a few different foods, such as corianders, white wines, and garden onions and in a lower concentration in rye bread, rosemaries, and parsnips. Vanillic acid has also been detected, but not quantified in, several different foods, such as salmonberries, vanilla, figs, red beetroots, and highbush blueberries. This could make vanillic acid a potential biomarker for the consumption of these foods. A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.
Structure
Thumb
Synonyms
ValueSource
4-Hydroxy-3-methoxybenzoic acidChEBI
4-Hydroxy-3-methoxybenzoateKegg
VanillateGenerator
3-Methoxy-4-hydroxybenzoateHMDB
3-Methoxy-4-hydroxybenzoic acidHMDB
4-Hydroxy-3-methoxy-benzoateHMDB
4-Hydroxy-3-methoxy-benzoic acidHMDB
4-Hydroxy-m-anisateHMDB
4-Hydroxy-m-anisic acidHMDB
Acide vanilliqueHMDB
p-VanillateHMDB
p-Vanillic acidHMDB
Protocatechuic acid 3-methyl esterHMDB
Acid, 4-hydroxy-3-methoxybenzoicHMDB
p Hydroxy m methoxy benzoic acidHMDB
4 Hydroxy 3 methoxybenzoic acidHMDB
Acid, vanillicHMDB
Acid, p-hydroxy-m-methoxy-benzoicHMDB
p-Hydroxy-m-methoxy-benzoic acidHMDB
Vanillic acidKEGG
2-Methoxy-4-carboxyphenolPhytoBank
Methylprotocatechuic acidPhytoBank
VAPhytoBank
m-Methoxy-p-hydroxy-benzoic acidPhytoBank
Chemical FormulaC8H8O4
Average Molecular Weight168.148
Monoisotopic Molecular Weight168.042258738
IUPAC Name4-hydroxy-3-methoxybenzoic acid
Traditional Namevanillic acid
CAS Registry Number121-34-6
SMILES
COC1=C(O)C=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
InChI KeyWKOLLVMJNQIZCI-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesPlantae; Eubacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point211.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.5 mg/mL at 14 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP1.43HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility5.7 g/LALOGPS
logP1.7ALOGPS
logP1.17ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0000484
DrugBank IDNot Available
Phenol Explorer Compound ID414
FoodDB IDFDB000846
KNApSAcK IDC00002682
Chemspider ID8155
KEGG Compound IDC06672
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVanillic acid
METLIN ID5471
PubChem Compound8468
PDB IDNot Available
ChEBI ID30816
References
General References
  1. Muskiet FA, Groen A: Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma. Clin Chem. 1979 Jul;25(7):1281-4. [PubMed:455649 ]
  2. Ebinger G, Verheyden R: On the occurence of vanillic acid in human brain and cerebrospinal fluid. J Neurol. 1976 Apr 23;212(2):133-8. [PubMed:57225 ]
  3. Lee BL, New AL, Kok PW, Ong HY, Shi CY, Ong CN: Urinary trans,trans-muconic acid determined by liquid chromatography: application in biological monitoring of benzene exposure. Clin Chem. 1993 Sep;39(9):1788-92. [PubMed:8375048 ]
  4. Dhananjaya BL, Nataraju A, Rajesh R, Raghavendra Gowda CD, Sharath BK, Vishwanath BS, D'Souza CJ: Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006 Sep 15;48(4):411-21. Epub 2006 Jul 7. [PubMed:16899266 ]