Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:31 UTC
NP-MRD IDNP0000013
Secondary Accession NumbersNone
Natural Product 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-methoxybenzoateKegg
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-methoxybenzoicHMDB
p Hydroxy m methoxy benzoic acidHMDB
4 Hydroxy 3 methoxybenzoic acidHMDB
Acid, vanillicHMDB
Acid, p-hydroxy-m-methoxy-benzoicHMDB
p-Hydroxy-m-methoxy-benzoic acidHMDB
2-Methoxy-4-carboxyphenolHMDB
Methylprotocatechuic acidHMDB
VAHMDB
m-Methoxy-p-hydroxy-benzoic acidHMDB
Vanillic acidKEGG
Chemical FormulaC8H8O4
Average Mass168.1480 Da
Monoisotopic Mass168.04226 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO, simulated)Varshavi.d262021-10-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Abutilon indicumPlant
Acer nikoenseKNApSAcK Database
Aganosma caryophyllata-
Ailanthus integrifoliaKNApSAcK Database
Ajuga taiwanensisKNApSAcK Database
Allium cepaFooDB
Allium sativumKNApSAcK Database
Alnus japonicaKNApSAcK Database
Amburana cearensisKNApSAcK Database
Amphibolis antarcticaKNApSAcK Database
Amphibolis griffithiiKNApSAcK Database
Anethum graveolensFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Aristolochia manshuriensisKNApSAcK Database
Aristolochia pubescensKNApSAcK Database
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Avena sativa L.FooDB
Begonia nantoensisKNApSAcK Database
Beta vulgaris ssp. ciclaFooDB
Brassica napus var. napusFooDB
Brassica oleracea var. italicaFooDB
Callicarpa integerrimaKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Carica papayaKNApSAcK Database
Carica papaya L.Plant
Casearia membranaceaKNApSAcK Database
Catharanthus roseusKNApSAcK Database
Ceratostigma willmottianumKNApSAcK Database
Chamomilla rectitaPlant
Chenopodium albumFooDB
Cichorium intybusKNApSAcK Database
Cinnamomum philippinenseKNApSAcK Database
Cinnamomum subaveniumPlant
Cinnamomum subavenium MIQ.KNApSAcK Database
Citrullus colocynthisPlant
Citrus paradisiFooDB
Citrus sudachiKNApSAcK Database
Cleidion spiciflorum (Burm. f.) Merr.KNApSAcK Database
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colubrina faralaotra subsp.trichocarpa.KNApSAcK Database
Coriandrum sativum L.FooDB
Crocus sativusKNApSAcK Database
Cuminum cyminumFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaFooDB
Cymodocea rotundataKNApSAcK Database
Cymodocea serrulataKNApSAcK Database
Cyperus rotundusPlant
Cyperus rotundus L.KNApSAcK Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • Adrian J. Parr, Annie Ng, and Keith W. Waldron Ester-Linked Phenolic Components of Carrot Cell Wa...
Derris scandensKNApSAcK Database
Dicliptera ripariaKNApSAcK Database
Dipsacus asperKNApSAcK Database
Elaeagnus pungensKNApSAcK Database
Elettaria cardamomumFooDB
Engelhardia roxburghianaKNApSAcK Database
Ephedra equisetinaKNApSAcK Database
Equsetum arvense-
Erica australisKNApSAcK Database
Eriocaulon buergerianumKNApSAcK Database
Fagara spp.KNApSAcK Database
Fagara tessmannii Engl.KNApSAcK Database
Fagopyrum esculentumFooDB
Falcaria vulgarisKNApSAcK Database
Ficus caricaFooDB
Ficus septicaKNApSAcK Database
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Ginkgo bilobaFooDB
Glehnia littoralisKNApSAcK Database
Glycine maxFooDB
Gomphrena celosioidesKNApSAcK Database
Gossypium mexicanumKNApSAcK Database
Grindelia aphanactisKNApSAcK Database
Gymnadenia conopsea R.BR.KNApSAcK Database
Halodule uninervisKNApSAcK Database
Halodule wrightiiKNApSAcK Database
Halophila engelmanniiKNApSAcK Database
Halophila hawaiianaKNApSAcK Database
Hibiscus taiwanensisKNApSAcK Database
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Humulus lupulusKNApSAcK Database
Hydrangea chinensisKNApSAcK Database
Hyoscyamus nigerKNApSAcK Database
Hyssopus officinalis L.FooDB
Juglans nigra L.FooDB
Lentinus edodes-
Leptolaena diospyroideaKNApSAcK Database
Leptolaena paucifloraKNApSAcK Database
Magnolia denudataKNApSAcK Database
Magnolia liliifloraKNApSAcK Database
Malus pumilaFooDB
Mangifera indicaKNApSAcK Database
Maranta arundinaceaFooDB
Matricaria chamomillaKNApSAcK Database
Matricaria recutitaFooDB
Medicago sativaKNApSAcK Database
Melia azedarachKNApSAcK Database
Melilotus messanensisKNApSAcK Database
Melissa officinalis L.FooDB
Mentha spicataFooDB
Microtropis fokienensisKNApSAcK Database
Microtropis japonicaKNApSAcK Database
Musa x paradisiacaFooDB
Neopicrorhiza scrophulariiflora-
Notopterygium incisumKNApSAcK Database
Ocimum basilicumFooDB
Olea europaeaFooDB
Opunitia dillenii HAW.-
Opuntia dilleniiKNApSAcK Database
Origanum majoranaFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
Oryza sativaFooDB
Oryza sativa cv. HeugjinjubyeoKNApSAcK Database
Oxalis corniculataKNApSAcK Database
Paeonia hybridaKNApSAcK Database
Panax ginsengKNApSAcK Database
Paratecoma koraiensisKNApSAcK Database
Pelargonium reniformeKNApSAcK Database
Peperomia duclouxii C. DC.KNApSAcK Database
Peperomia suiKNApSAcK Database
Petroselinum crispumFooDB
Phellodendron amurense var.wilsoniiKNApSAcK Database
Phellodendron japonicum MAXIMKNApSAcK Database
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllospadix scouleriKNApSAcK Database
Phyllospadix serrulatusKNApSAcK Database
Picea ajanensisKNApSAcK Database
Picea jezoensis var. jezoensisPlant
Picea obovataKNApSAcK Database
Picrorhiza kurrooaKNApSAcK Database
Picrorhiza kurrosaKNApSAcK Database
Picrorrhiza scrophulariaeflora-
Pimpinella anisumFooDB
Pinus sibiricaKNApSAcK Database
Pisum sativumFooDB
Plantago lanceolataKNApSAcK Database
Plantago majorKNApSAcK Database
Plantago mediaKNApSAcK Database
Polytrichum communeKNApSAcK Database
Populus pseudosimoniiKNApSAcK Database
Posidonia australisKNApSAcK Database
Posidonia oceanicaKNApSAcK Database
Prunus armeniacaFooDB
Prunus aviumKNApSAcK Database
Prunus cerasusFooDB
Prunus dulcisFooDB
Pseudolarix kaempferi Gord.KNApSAcK Database
Pterocarpus santalinusKNApSAcK Database
Punica granatumKNApSAcK Database
Ranunculus baudotiiKNApSAcK Database
Rhaponticum carthamoidesKNApSAcK Database
Rheum rhabarbarumFooDB
Rohdea chinensisPlant
Rosa caninaKNApSAcK Database
Rubia yunnanensisKNApSAcK Database
Rubus idaeusFooDB
Rubus spectabilisFooDB
Salvia officinalisKNApSAcK Database
Salvia rosmarinusFooDB
Sarcolaeana multiflora-
Scrophularia frutescensPlant
Scrophularis sambucifolia-
Secale cerealeFooDB
Sesamum indicumFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum tuberosumKNApSAcK Database
Solori scandensPlant
Sparganium stoloniferumKNApSAcK Database
Spiraea formosanaKNApSAcK Database
Strobilanthes crispusPlant
Syringodium filiformeKNApSAcK Database
Syringodium isoetifoliumKNApSAcK Database
Taraxacum formosanumKNApSAcK Database
Taraxacum officinaleFooDB
Taxus baccataKNApSAcK Database
Terminalia catappaPlant
Terminalia chebulaPlant
Terminalia nigrovenulosaPlant
Tetracentron sinenseKNApSAcK Database
Thalassia hemprichiiKNApSAcK Database
Thalassia testudinumKNApSAcK Database
Thalassodendron ciliatumKNApSAcK Database
Theobroma cacaoFooDB
Thymus vulgarisFooDB
Toona ciliataKNApSAcK Database
Trachelospermum asiaticumKNApSAcK Database
Tribulus terrestrisPlant
Trichosanthes kirilowiiKNApSAcK Database
Trifolium pratensePlant
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Tupistra chinensisKNApSAcK Database
Vaccinium corymbosumFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Vaccinium vitis-idaeaFooDB
VanillaFooDB
Veronica peregrina L.KNApSAcK Database
Viscum coloratumKNApSAcK Database
Vitis vinifera L.FooDB
Vittaria anguste-elongataKNApSAcK Database
Withania somniferaPlant
Zanthoxylum simulansKNApSAcK Database
Zea mays L.KNApSAcK Database
Zingiber officinaleFooDB
Zostera marinaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Pseudomonas pseudoalcaligenesKNApSAcK Database
Streptomyces sp. GW23/1540KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point211.5 °Chttps://en.wikipedia.org/wiki/Vanillic_acid
Boiling Point353.43 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.5 mg/mL at 14 °CYalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogP1.43Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (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
Polarizability15.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000484
DrugBank IDNot Available
Phenol Explorer Compound ID414
FoodDB 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
Good Scents IDrw1051611
References
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 ]
  5. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]