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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:52 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 flavouring and scent agent that produces a pleasant, creamy odour. 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-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'nucleotidase activity (PMID: 16899266 ). Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072 , 10543794 , 11728709 , 9579070 ).
Structure
Thumb
Synonyms
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=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
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
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point211.5 °CNot Available
Boiling Point353.43 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.5 mg/mL at 14 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP1.43HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos136.22430932474
[M+H]+Not Available136.26http://allccs.zhulab.cn/database/detail?ID=AllCCS00000527
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected and Quantified3.45 +/- 1.002 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID414
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000172
Good Scents IDrw1051611
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

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-O-sulfatedetails