Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2024-11-29 22:27:57 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
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
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
    Physico-Chemical Properties - Experimental
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-0gb9-6900000000-c13506201c3612fc7ca52015-03-01View Spectrum
    GC-MSVanillic acid, 2 TMS, GC-MS Spectrumsplash10-0hp2-2691000000-8409d9c758b023c6576bSpectrum
    GC-MSVanillic acid, non-derivatized, GC-MS Spectrumsplash10-0gb9-2900000000-ccd8d4a214bc1a7f08c5Spectrum
    GC-MSVanillic acid, non-derivatized, GC-MS Spectrumsplash10-0hp2-2691000000-8409d9c758b023c6576bSpectrum
    GC-MSVanillic acid, non-derivatized, GC-MS Spectrumsplash10-0g0b-2981000000-a58243e35d1e3a64d2aaSpectrum
    Predicted GC-MSVanillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4i-1900000000-851f4a1738be8dd91d47Spectrum
    Predicted GC-MSVanillic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dj-7390000000-18c5f822b380ea00aa26Spectrum
    Predicted GC-MSVanillic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSVanillic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSVanillic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSVanillic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSVanillic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSVanillic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0gb9-0900000000-0aa6709c16899e2220862012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0900000000-9aa2b9d4aa89e6ac12ab2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-0900000000-6d98ebfa89f4b8ee1e6b2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0gb9-2900000000-babed327a6e49c6f7d512012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-105f33777cee542cf6df2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-05fr-1900000000-a502792703fa2f2110352012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-5900000000-037ef32f4c68a5252b922012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9800000000-ecd60ac022f5fee1d5ef2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-066u-9300000000-c63f7f792794f3c748a02012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0923211100-7e9f357f7429cff055242017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0923211100-7e9f357f7429cff055242017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01f2017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01f2017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0923211100-7e9f357f7429cff055242017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0900000000-8e112ffa4dcc7c08b0fd2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01f2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0uxr-0900000000-29a2674dccd1fa478bd52017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-105f33777cee542cf6df2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05fr-1900000000-c4ce596998934098267b2017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-342964fa3647815dd1d22016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-f16c365899f9d95733d32016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-5900000000-e5593db0a935e1534bc62016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-6a1a2db582acd95348ea2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0600-0900000000-eda6cfe601d63ed00f8d2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-b2c1e3f6b255e94a10af2016-09-12View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, DMSO, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, DMSO, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    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
    Processing...
    Biological Effects and Interactions
    Health Effects / Bioactivities
    EnzymesNot Available
    Pathways
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    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.