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Showing Compound 3-Methoxy-4-hydroxyphenylacetic acid (FDB001783)

Record Information
Version1.0
Creation date2010-04-08 22:05:06 UTC
Update date2019-11-26 02:56:40 UTC
Primary IDFDB001783
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methoxy-4-hydroxyphenylacetic acid
DescriptionHomovanillic acid, also known as vanillacetate or homovanillate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Homovanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Homovanillic acid exists in all living species, ranging from bacteria to humans. Homovanillic acid is found, on average, in the highest concentration within olives and beers. Homovanillic acid has also been detected, but not quantified in, avocado and milk (cow). This could make homovanillic acid a potential biomarker for the consumption of these foods. Homovanillic acid is a potentially toxic compound.
CAS Number306-08-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(4-Hydroxy-3-methoxyphenyl)acetic acidChEBI
3-Methoxy-4-hydroxyphenylacetateChEBI
3-Methoxy-4-hydroxyphenylacetic acidChEBI
4-Hydroxy-3-methoxybenzeneacetic acidChEBI
HVAChEBI
Vanillacetic acidChEBI
(4-Hydroxy-3-methoxyphenyl)acetateGenerator
4-Hydroxy-3-methoxybenzeneacetateGenerator
VanillacetateGenerator
HomovanillateGenerator
3-Methoxy-4-hydroxy-phenylacetic acidHMDB
4-Hydroxy 3-methoxyphenylacetic acidHMDB
4-Hydroxy-3-methoxyphenylacetic acidHMDB
HomovanilateHMDB
Homovanilic acidHMDB
Homovanillinic acidHMDB
VanilacetateHMDB
Vanilacetic acidHMDB
3 Methoxy 4 hydroxyphenylacetic acidHMDB
Acid, 3-methoxy-4-hydroxyphenylaceticHMDB
Acid, 4-hydroxy-3-methoxyphenylaceticHMDB
4 Hydroxy 3 methoxyphenylacetic acidHMDB
Acid, homovanillicHMDB
3'-Methoxy-4'-hydroxyphenylacetic acidHMDB
3’-methoxy-4’-hydroxyphenylacetic acidHMDB
4'-Hydroxy-3'-methoxy-phenylacetic acidHMDB
2-(4-Hydroxy-3-methoxyphenyl)acetic acidHMDB
4'-Hydroxy-3'-methoxyphenylacetic acidHMDB
HMPAbiospider
Homovanillic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility2.72 g/LALOGPS
logP1.02ALOGPS
logP1.15ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.81 m³·mol⁻¹ChemAxon
Polarizability17.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O4
IUPAC name2-(4-hydroxy-3-methoxyphenyl)acetic acid
InChI IdentifierInChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
InChI KeyQRMZSPFSDQBLIX-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(CC(O)=O)=CC=C1O
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
Classification
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

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 stateNot Available
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting Point138-140 oC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logP0.33LAHANN,TR ET AL. (1989)
    Experimental pKa4.41
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-b8c848b70c066282b36f2014-09-20View Spectrum
    GC-MS3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-056r-1962000000-4f8e427392aa8e136095Spectrum
    GC-MS3-Methoxy-4-hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrumsplash10-056r-2972000000-f53a7b3ac40c099e3c99Spectrum
    GC-MS3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9800000000-def178a40b9d8cc16724Spectrum
    GC-MS3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-06vi-0596000000-729a4b24107b98261cb2Spectrum
    GC-MS3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-056r-1962000000-4f8e427392aa8e136095Spectrum
    GC-MS3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-056r-2972000000-f53a7b3ac40c099e3c99Spectrum
    GC-MS3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-056r-1962000000-24557ef3db49c59cd5ddSpectrum
    Predicted GC-MS3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1900000000-cb0e3eb7a6d9e785a2f8Spectrum
    Predicted GC-MS3-Methoxy-4-hydroxyphenylacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01w0-9352000000-0e2f11bc503dd5ce6345Spectrum
    Predicted GC-MS3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS3-Methoxy-4-hydroxyphenylacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS3-Methoxy-4-hydroxyphenylacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS3-Methoxy-4-hydroxyphenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS3-Methoxy-4-hydroxyphenylacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS3-Methoxy-4-hydroxyphenylacetic 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)splash10-000i-0900000000-994a78c607c1b6a724d22012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00fr-4900000000-ca5ef14a72dcdf3cf9fe2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9700000000-44f2784ec5407e93ea572012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0019-0900000000-aafe8aee1cf8c42b941a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-1900000000-313fe6eb451badd5c0522012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0609-6900000000-11aa4fb169e782205ea32012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-9200000000-637a59b417fe2b2e7f582012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-9000000000-7b87b58730add4511c8a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0019-0900000000-aafe8aee1cf8c42b941a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-313fe6eb451badd5c0522017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0609-6900000000-11aa4fb169e782205ea32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9200000000-1bc951858c2e658a79af2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-7b87b58730add4511c8a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0900000000-0c3c4c703b4b9743a5212017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0900000000-a5e048e5e58ed8e57ecd2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-0079-0900000000-35fbf40336719c96dd3d2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-b408942abbf2cafac06e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-39dd2b8775ad5c5ec2f02021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-4900000000-c9fd7643f48c0e43dc872021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-57e5685e37a2d70f9ab42015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0900000000-b8470b9851db4df96b612015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-3900000000-2690d7c586d4f7c3dccf2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0900000000-713f0600845faa67fec32015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-0900000000-30a79a8a4d5cf0ffc8642015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-2900000000-6f967f9e7f7117a9d1e42015-04-25View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDC05582
    Pubchem Compound ID1738
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID574
    DrugBank IDNot Available
    HMDB IDHMDB00118
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke ID4-HYDROXY-3-METHOXYPHENYLACETIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00029504
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDHomovanillic acid
    Phenol-Explorer Metabolite ID574
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    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.