Record Information
Version1.0
Created at2020-03-18 23:21:44 UTC
Updated at2020-12-07 19:06:55 UTC
CannabisDB IDCDB006148
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameVanillic acid
DescriptionVanillic acid, also known as vanillate, 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. Vanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillic acid is a phenolic acid or chlorogenic acid that is an oxidized form of vanillin. Vanillic acid is also an intermediate in the production of vanillin from ferulic acid. It is found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. Açaí oil is particularly rich in vanillic acid (1,616 ± 94 mg/kg). Vanillic acid is also found in wine and vinegar.Vanillic acid is a metabolic by-product 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 also a microbial metabolite found in several bacterial genera including Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072 , 10543794 , 11728709 , 9579070 ).
Structure
Thumb
Synonyms
ValueSource
4-HYDROXY-3-methoxybenzoATEChEBI
4-HYDROXY-3-methoxybenzoic acidGenerator
VanillateGenerator
Vanillic acidGenerator
Chemical FormulaC8H7O4
Average Molecular Weight167.14
Monoisotopic Molecular Weight167.0344
IUPAC Name4-hydroxy-3-methoxybenzoate
Traditional Name4-hydroxy-3-methoxybenzoate
CAS Registry Number6746-48-1
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)/p-1
InChI KeyWKOLLVMJNQIZCI-UHFFFAOYSA-M
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
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic anion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point210 - 213 °CWikipedia
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.04ALOGPS
logP1.17ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.59 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.6 m³·mol⁻¹ChemAxon
Polarizability15.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-35ba9477c2a80f8e5c53Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0900000000-eb2178b1865054dab1ceSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-7900000000-dbf28dfc72f92a18a175Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-626d449dddc4d2d47ec5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-6a319e19fb40b9ad2b59Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9600000000-3f1b035788ad593819b9Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.006 mg/g dry wt
    • Jiamin Zheng, Yil...
details
GabriolaDetected and Quantified0.018 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Island HoneyDetected and Quantified0.005 mg/g dry wt
    • Jiamin Zheng, Yil...
details
QuadraDetected and Quantified0.01 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Tangerine DreamDetected and Quantified0.007 mg/g dry wt
    • Jiamin Zheng, Yil...
details
HMDB IDNot Available
DrugBank IDDB02130
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVanillic acid
METLIN IDNot Available
PubChem Compound23199
PDB IDNot Available
ChEBI ID16632
References
General References
  1. 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. doi: 10.1016/j.toxicon.2006.06.017. Epub 2006 Jul 7. [PubMed:16899266 ]
  2. Achterholt S, Priefert H, Steinbuchel A: Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol. 2000 Dec;54(6):799-807. doi: 10.1007/s002530000431. [PubMed:11152072 ]
  3. Overhage J, Priefert H, Steinbuchel A: Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl Environ Microbiol. 1999 Nov;65(11):4837-47. [PubMed:10543794 ]
  4. Plaggenborg R, Steinbuchel A, Priefert H: The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett. 2001 Nov 27;205(1):9-16. doi: 10.1111/j.1574-6968.2001.tb10918.x. [PubMed:11728709 ]
  5. Venturi V, Zennaro F, Degrassi G, Okeke BC, Bruschi CV: Genetics of ferulic acid bioconversion to protocatechuic acid in plant-growth-promoting Pseudomonas putida WCS358. Microbiology. 1998 Apr;144 ( Pt 4):965-73. doi: 10.1099/00221287-144-4-965. [PubMed:9579070 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125