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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:28:09 UTC
HMDB IDHMDB0000484
Secondary Accession Numbers
  • HMDB00484
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
ValueSource
4-Hydroxy-3-methoxybenzoic acidChEBI
4-Hydroxy-3-methoxybenzoateGenerator
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-methoxybenzoicMeSH
P Hydroxy m methoxy benzoic acidMeSH
4 Hydroxy 3 methoxybenzoic acidMeSH
Acid, vanillicMeSH
Acid, P-hydroxy-m-methoxy-benzoicMeSH
P-Hydroxy-m-methoxy-benzoic acidMeSH
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
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

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
Polarizability15.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0hp2-2691000000-8409d9c758b023c6576bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gb9-2900000000-ccd8d4a214bc1a7f08c5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0hp2-2691000000-8409d9c758b023c6576bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0g0b-2981000000-a58243e35d1e3a64d2aaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4i-1900000000-851f4a1738be8dd91d47View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-7390000000-18c5f822b380ea00aa26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0gb9-0900000000-0aa6709c16899e222086View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0900000000-9aa2b9d4aa89e6ac12abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-0900000000-6d98ebfa89f4b8ee1e6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0gb9-2900000000-babed327a6e49c6f7d51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-105f33777cee542cf6dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-05fr-1900000000-a502792703fa2f211035View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-5900000000-037ef32f4c68a5252b92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9800000000-ecd60ac022f5fee1d5efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-066u-9300000000-c63f7f792794f3c748a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0923211100-7e9f357f7429cff05524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0923211100-7e9f357f7429cff05524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0923211100-7e9f357f7429cff05524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0900000000-8e112ffa4dcc7c08b0fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0uxr-0900000000-29a2674dccd1fa478bd5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-105f33777cee542cf6dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05fr-1900000000-c4ce596998934098267bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-342964fa3647815dd1d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-f16c365899f9d95733d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-5900000000-e5593db0a935e1534bc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-6a1a2db582acd95348eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0600-0900000000-eda6cfe601d63ed00f8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-b2c1e3f6b255e94a10afView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0gb9-6900000000-c13506201c3612fc7ca5View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.8 (2.0-8.1) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.272 +/- 0.036 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.248 +/- 0.026 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.295 +/- 0.036 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.314 +/- 0.043 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.255 +/- 0.024 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.245 +/- 0.027 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.229 +/- 0.024 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.901 +/- 0.71 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
FecesDetected and Quantified5.828 +/- 3.0925 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.423 +/- 13.857 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.542 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.661 +/- 4.996 nmol/g of fecesAdult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 414 details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified11.2 +/- 3.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.43 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0750-19.200 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.991 +/- 3.942 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified1.6 (0.6-3.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.596 +/- 0.131 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.855 +/- 0.512 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified1.0 (0.0-2.5) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.574 +/- 0.184 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected and Quantified3.45 +/- 1.002 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
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
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)Download (PDF)
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 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Vanillic acid → 6-(4-carboxy-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vanillic acid → 3,4,5-trihydroxy-6-(4-hydroxy-3-methoxybenzoyloxy)oxane-2-carboxylic aciddetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
Vanillic acid → Vanilloylglycinedetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Vanillic acid → Vanillic acid 4-sulfatedetails