Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2018-05-28 23:03:37 UTC
Primary IDFDB000846
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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).
CAS Number121-34-6
Structure
Thumb
Synonyms
SynonymSource
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
4 Hydroxy 3 methoxybenzoic Acidbiospider
4-hydroxy-3-methoxy-Benzoatebiospider
4-hydroxy-3-methoxy-Benzoic acidbiospider
4-Hydroxy-3-methoxybenzoic acid (vanillic acid)biospider
4-hydroxy-m-Anisatebiospider
4-hydroxy-m-Anisic acidbiospider
Acid, 4-Hydroxy-3-methoxybenzoicbiospider
Benzoic acid, 4-hydroxy-3-methoxy-biospider
m-Anisic acid, 4-hydroxy-biospider
P hydroxy m methoxy benzoic acidbiospider
P-hydroxy-m-methoxy-benzoic acidbiospider
P-hydroxy-m-methoxy-benzonic acidbiospider
P-vanillatebiospider
P-vanillic acidbiospider
Protocatechuic acid, 3-methyl esterbiospider
VAbiospider
Va (van)biospider
VNLbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H8O4
IUPAC name4-hydroxy-3-methoxybenzoic acid
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(O)C=CC(=C1)C(O)=O
Average Molecular Weight168.148
Monoisotopic Molecular Weight168.042258738
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 57.14%; H 4.80%; O 38.06%DFC
    Melting PointMp 210°DFC
    Boiling PointNot Available
    Experimental Water Solubility1.5 mg/mL at 14 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
    Experimental logP1.43HANSCH,C ET AL. (1995)
    Experimental pKapKa2 9.39 (25°)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    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
    ChemSpider ID8155
    ChEMBL IDCHEMBL120568
    KEGG Compound IDC06672
    Pubchem Compound ID8468
    Pubchem Substance IDNot Available
    ChEBI ID16632
    Phenol-Explorer ID414
    DrugBank IDDB02130
    HMDB IDHMDB00484
    CRC / DFC (Dictionary of Food Compounds) IDBJS05-K:BJS01-G
    EAFUS ID3829
    Dr. Duke ID4-HYDROXY-3-METHOXY-BENZOIC-ACID|VANILLIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00002682
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1051611
    SuperScent IDNot Available
    Wikipedia IDVA
    Phenol-Explorer Metabolite ID414
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
    allelopathicDUKE
    anti helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti fatigue52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
    anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti peroxidantDUKE
    anti radicularDUKE
    anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti sicklingDUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    ascaricide33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    cholereticDUKE
    fungicide24127 A substance used to destroy fungal pests.DUKE
    immunosuppressant35705 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.DUKE
    laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    ubiquiotDUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    dairy
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    milky
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    sweet
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    creamy
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    powdery
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    vanilla
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    bean
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.