Human Metabolome Database Version 3.5

Showing metabocard for Vanillic acid (HMDB00484)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:27:01 -0600
HMDB ID HMDB00484
Secondary Accession Numbers None
Metabolite Identification
Common Name Vanillic acid
Description Vanillic 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C8H8O4
Average Molecular Weight 168.1467
Monoisotopic Molecular Weight 168.042258744
IUPAC Name 4-hydroxy-3-methoxybenzoic acid
Traditional IUPAC Name vanillic acid
CAS Registry Number 121-34-6
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 Key WKOLLVMJNQIZCI-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Hydroxybenzoic 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 Parent Hydroxybenzoic Acid Derivatives
Ontology
Status Detected and Quantified
Origin
  • Food
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 211.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.5 mg/mL at 14 °C YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP 1.43 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 5.7 g/L ALOGPS
LogP 1.70 ALOGPS
LogP 1.17 ChemAxon
LogS -1.47 ALOGPS
pKa (strongest acidic) 4.16 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 41.76 ChemAxon
Polarizability 15.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
4.8 (2.0-8.1) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.272 +/- 0.036 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.248 +/- 0.026 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.295 +/- 0.036 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.314 +/- 0.043 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.255 +/- 0.024 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.245 +/- 0.027 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.229 +/- 0.024 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.901 +/- 0.71 uM Adult (>18 years old) Male Comment Normal
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414
  • Not Applicable
Urine Detected and Quantified
11.2 +/- 3.2 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.6 (0.6-3.3) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.596 +/- 0.131 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
0.855 +/- 0.512 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
1.0 (0.0-2.5) umol/mmol creatinine Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
0.574 +/- 0.184 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Comment Hypertension (mild)
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Comment Hypertension (mild)
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB02130 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID 414 Link_out
Phenol Explorer Metabolite ID 414 Link_out
FoodDB ID FDB000846
KNApSAcK ID C00002682 Link_out
Chemspider ID 8155 Link_out
KEGG Compound ID C06672 Link_out
BioCyc ID CPD-2042 Link_out
BiGG ID Not Available
Wikipedia Link VA Link_out
NuGOwiki Link HMDB00484 Link_out
Metagene Link HMDB00484 Link_out
METLIN ID 5471 Link_out
PubChem Compound 8468 Link_out
PDB ID Not Available
ChEBI ID 30816 Link_out
References
Synthesis Reference Pearl, 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) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  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 Link_out