Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:27:01 UTC
HMDB IDHMDB00484
Secondary Accession NumbersNone
Metabolite Identification
Common NameVanillic acid
DescriptionVanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5'nucleotidase activity. (PMID: 16899266 ).
Structure
Thumb
Synonyms
  1. 3-Methoxy-4-hydroxybenzoate
  2. 3-Methoxy-4-hydroxybenzoic acid
  3. 4-Hydroxy-3-methoxy-Benzoate
  4. 4-Hydroxy-3-methoxy-Benzoic acid
  5. 4-Hydroxy-3-methoxybenzoate
  6. 4-Hydroxy-3-methoxybenzoic acid
  7. 4-Hydroxy-m-Anisate
  8. 4-Hydroxy-m-Anisic acid
  9. Acide vanillique
  10. p-Vanillate
  11. p-Vanillic acid
  12. Protocatechuic acid 3-methyl ester
  13. Vanillate
  14. Vanillic acid
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name4-hydroxy-3-methoxybenzoic acid
Traditional IUPAC Namevanillic acid
CAS Registry Number121-34-6
SMILES
COC1=CC(=CC=C1O)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
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassBenzoic Acid and Derivatives
Sub ClassHydroxybenzoic Acid Derivatives
Other Descriptors
  • Methoxyphenols and Derivatives
  • Organic Compounds
  • methoxybenzoic acid(ChEBI)
  • monohydroxybenzoic acid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Benzoyl
  • Carboxylic Acid
  • Phenol
  • Phenol Derivative
Direct ParentHydroxybenzoic Acid Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Food
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 area66.76ChemAxon
rotatable bond count2ChemAxon
refractivity41.76ChemAxon
polarizability15.87ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified4.8 (2.0-8.1) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.272 +/- 0.036 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified0.248 +/- 0.026 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified0.295 +/- 0.036 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified0.314 +/- 0.043 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified0.255 +/- 0.024 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified0.245 +/- 0.027 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified0.229 +/- 0.024 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified0.901 +/- 0.71 uMAdult (>18 years old)MaleCommentNormal
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
UrineDetected and Quantified11.2 +/- 3.2 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified1.6 (0.6-3.3) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified0.596 +/- 0.131 umol/mmol creatinineAdult (>18 years old)MaleCommentNormal
UrineDetected and Quantified0.855 +/- 0.512 umol/mmol creatinineAdult (>18 years old)MaleCommentNormal
UrineDetected and Quantified1.0 (0.0-2.5) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
UrineDetected and Quantified0.574 +/- 0.184 umol/mmol creatinineAdult (>18 years old)MaleCommentNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentHypertension (mild)
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentHypertension (mild)
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02130
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID414
Phenol Explorer Metabolite ID414
FoodDB IDFDB000846
KNApSAcK IDC00002682
Chemspider ID8155
KEGG Compound IDC06672
BioCyc IDCPD-2042
BiGG IDNot Available
Wikipedia LinkVA
NuGOwiki LinkHMDB00484
Metagene LinkHMDB00484
METLIN ID5471
PubChem Compound8468
PDB IDNot Available
ChEBI ID30816
References
Synthesis ReferencePearl, Irwin A. Reactions of vanillin and its derived compounds. I. The reaction of vanillin with silver oxide. Journal of the American Chemical Society (1946), 68 429-32.
Material Safety Data Sheet (MSDS)Not Available
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