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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 20:22:28 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
Vanillic acidKEGG
2-Methoxy-4-carboxyphenolPhytoBank
Methylprotocatechuic acidPhytoBank
VAPhytoBank
m-Methoxy-p-hydroxy-benzoic acidPhytoBank
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
1D NMR1H NMR Spectrum (1D, DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, DMSO, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Acer nikoenseKNApSAcK Database
Ailanthus integrifoliaKNApSAcK Database
Ajuga taiwanensisKNApSAcK Database
Allium sativumKNApSAcK Database
Alnus japonicaKNApSAcK Database
Amburana cearensisKNApSAcK Database
Amphibolis antarcticaKNApSAcK Database
Amphibolis griffithiiKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Aristolochia manshuriensisKNApSAcK Database
Aristolochia pubescensKNApSAcK Database
Begonia nantoensisKNApSAcK Database
Callicarpa integerrimaKNApSAcK Database
Carica papayaKNApSAcK Database
Casearia membranaceaKNApSAcK Database
Catharanthus roseusKNApSAcK Database
Ceratostigma willmottianumKNApSAcK Database
Cichorium intybusKNApSAcK Database
Cinnamomum philippinenseKNApSAcK Database
Cinnamomum subavenium MIQ.KNApSAcK Database
Citrus sudachiKNApSAcK Database
Cleidion spiciflorum (Burm. f.) Merr.KNApSAcK Database
Colubrina faralaotra subsp.trichocarpa.KNApSAcK Database
Crocus sativusKNApSAcK Database
Curcuma domesticaKNApSAcK Database
Cymodocea rotundataKNApSAcK Database
Cymodocea serrulataKNApSAcK Database
Cyperus rotundus L.KNApSAcK Database
Derris scandensKNApSAcK Database
Dicliptera ripariaKNApSAcK Database
Dipsacus asperKNApSAcK Database
Elaeagnus pungensKNApSAcK Database
Engelhardia roxburghianaKNApSAcK Database
Ephedra equisetinaKNApSAcK Database
Erica australisKNApSAcK Database
Eriocaulon buergerianumKNApSAcK Database
Fagara spp.KNApSAcK Database
Fagara tessmannii Engl.KNApSAcK Database
Falcaria vulgarisKNApSAcK Database
Ficus septicaKNApSAcK Database
Glehnia littoralisKNApSAcK Database
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
Humulus lupulusKNApSAcK Database
Hydrangea chinensisKNApSAcK Database
Hyoscyamus nigerKNApSAcK Database
Leptolaena diospyroideaKNApSAcK Database
Leptolaena paucifloraKNApSAcK Database
Magnolia denudataKNApSAcK Database
Magnolia liliifloraKNApSAcK Database
Mangifera indicaKNApSAcK Database
Matricaria chamomillaKNApSAcK Database
Medicago sativaKNApSAcK Database
Melia azedarachKNApSAcK Database
Melilotus messanensisKNApSAcK Database
Microtropis fokienensisKNApSAcK Database
Microtropis japonicaKNApSAcK Database
Notopterygium incisumKNApSAcK Database
Opuntia dilleniiKNApSAcK Database
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
Phellodendron amurense var.wilsoniiKNApSAcK Database
Phellodendron japonicum MAXIMKNApSAcK Database
Phyllospadix scouleriKNApSAcK Database
Phyllospadix serrulatusKNApSAcK Database
Picea ajanensisKNApSAcK Database
Picea obovataKNApSAcK Database
Picrorhiza kurrooaKNApSAcK Database
Picrorhiza kurrosaKNApSAcK Database
Pinus sibiricaKNApSAcK Database
Plantago lanceolataKNApSAcK Database
Plantago majorKNApSAcK Database
Plantago mediaKNApSAcK Database
Polytrichum communeKNApSAcK Database
Populus pseudosimoniiKNApSAcK Database
Posidonia australisKNApSAcK Database
Posidonia oceanicaKNApSAcK Database
Prunus aviumKNApSAcK Database
Pseudolarix kaempferi Gord.KNApSAcK Database
Pterocarpus santalinusKNApSAcK Database
Punica granatumKNApSAcK Database
Ranunculus baudotiiKNApSAcK Database
Rhaponticum carthamoidesKNApSAcK Database
Rosa caninaKNApSAcK Database
Rubia yunnanensisKNApSAcK Database
Salvia officinalisKNApSAcK Database
Solanum tuberosumKNApSAcK Database
Sparganium stoloniferumKNApSAcK Database
Spiraea formosanaKNApSAcK Database
Syringodium filiformeKNApSAcK Database
Syringodium isoetifoliumKNApSAcK Database
Taraxacum formosanumKNApSAcK Database
Taxus baccataKNApSAcK Database
Tetracentron sinenseKNApSAcK Database
Thalassia hemprichiiKNApSAcK Database
Thalassia testudinumKNApSAcK Database
Thalassodendron ciliatumKNApSAcK Database
Toona ciliataKNApSAcK Database
Trachelospermum asiaticumKNApSAcK Database
Trichosanthes kirilowiiKNApSAcK Database
Triticum aestivumKNApSAcK Database
Tupistra chinensisKNApSAcK Database
Veronica peregrina L.KNApSAcK Database
Viscum coloratumKNApSAcK Database
Vittaria anguste-elongataKNApSAcK Database
Zanthoxylum simulansKNApSAcK Database
Zea mays L.KNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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,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
Polarizability15.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
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 ]