• Home
• Browse »
  • Metabolite Browse
  • Diseases
  • Pathways
  • Biofluids
  • Classes
  • Protein
  • Metabolite Library
• Search »
  • Chem Query
  • Text Query
  • Sequence Search
  • Advanced Search
  • MS Search
  • MS/MS Search
  • GC/MS Search
  • 1D NMR Search
  • 2D NMR Search
• About »
  • About the HMDB
  • Release Notes
  • Citing the HMDB
  • What's New
  • Statistics
  • Data Sources
  • Other Databases
• Downloads
• Contact Us

Human Metabolome Database Version 3.5

Showing metabocard for Vanillic acid (HMDB00484)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2005-11-16 08:48:42 -0700
Update Date	2013-02-08 17:08:40 -0700
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 ).
Structure	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	3-Methoxy-4-hydroxybenzoate 3-Methoxy-4-hydroxybenzoic acid 4-Hydroxy-3-methoxy-Benzoate 4-Hydroxy-3-methoxy-Benzoic acid 4-Hydroxy-3-methoxybenzoate 4-Hydroxy-3-methoxybenzoic acid 4-Hydroxy-m-Anisate 4-Hydroxy-m-Anisic acid Acide vanillique p-Vanillate p-Vanillic acid Protocatechuic acid 3-methyl ester Vanillate 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 Comments Blood Detected and Quantified 4.8 (2.0-8.1) uM Adult (>18 years old) Both Normal Not Available Blood Detected and Quantified 0.272 +/- 0.036 uM Adult (>18 years old) Male Normal Before ingestion of water Blood Detected and Quantified 0.248 +/- 0.026 uM Adult (>18 years old) Male Normal 2 h after ingestion of water Blood Detected and Quantified 0.295 +/- 0.036 uM Adult (>18 years old) Male Normal Before ingestion of quercetin Blood Detected and Quantified 0.314 +/- 0.043 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of quercetin Blood Detected and Quantified 0.255 +/- 0.024 uM Adult (>18 years old) Male Normal Before ingestion of (-)-epicathechin Blood Detected and Quantified 0.245 +/- 0.027 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of (-)-epicathechin Blood Detected and Quantified 0.229 +/- 0.024 uM Adult (>18 years old) Male Normal Before ingestion of epigallocatechin gallate Blood Detected and Quantified 0.901 +/- 0.71 uM Adult (>18 years old) Male Normal 2 h after ingestion of 200 mg of... Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 414 Not Available Urine Detected and Quantified 11.2 +/- 3.2 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 1.6 (0.6-3.3) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR Urine Detected and Quantified 0.596 +/- 0.131 umol/mmol creatinine Adult (>18 years old) Male Normal Before ingestion of 200 mg of quercetin Urine Detected and Quantified 0.855 +/- 0.512 umol/mmol creatinine Adult (>18 years old) Male Normal 5-h after ingestion of 200 mg of quercetin Urine Detected and Quantified 1.0 (0.0-2.5) umol/mmol creatinine Adult (>18 years old) Not Specified Normal Not Available Urine Detected and Quantified 0.574 +/- 0.184 umol/mmol creatinine Adult (>18 years old) Male Normal 5-h after ingestion of 200 mg of quercetin,...
Abnormal Concentrations
	Biofluid Status Value Age Sex Condition Comments Urine Detected and not Quantified Not Applicable Adult (>18 years old) Both Hypertension (mild) After 4-wk comsumption of polyphenol-rich MIX.... Urine Detected and not Quantified Not Applicable Adult (>18 years old) Both Hypertension (mild) After 4-wk comsumption of polyphenol-rich GJX...
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank ID	DB02130
Phenol Explorer Compound ID	414
Phenol Explorer Metabolite ID	414
FoodDB ID	FDB000846
KNApSAcK ID	C00002682
Chemspider ID	8155
KEGG Compound ID	C06672
BioCyc ID	CPD-2042
BiGG ID	Not Available
Wikipedia Link	VA
NuGOwiki Link	HMDB00484
Metagene Link	HMDB00484
METLIN ID	5471
PubChem Compound	8468
PDB ID	Not Available
ChEBI ID	30816
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	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 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 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

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government.