Back to Compounds

3,4-Dihydroxyphenylacetic acid (FDB000316)

Record Information
Version1.0
Creation date2010-04-08 22:04:31 UTC
Update date2019-11-26 02:54:37 UTC
Primary IDFDB000316
Secondary Accession Numbers
  • FDB030384
Chemical Information
FooDB Name3,4-Dihydroxyphenylacetic acid
Description3,4-Dihydroxybenzeneacetic acid, also known as 3,4-dihydroxyphenyl acetate or dopacetic acid, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxybenzeneacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxybenzeneacetic acid exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydroxybenzeneacetic acid is found, on average, in the highest concentration within olives and beers. 3,4-Dihydroxybenzeneacetic acid has also been detected, but not quantified in, several different foods, such as alfalfa, caraway, sunflowers, oriental wheats, and hazelnuts. This could make 3,4-dihydroxybenzeneacetic acid a potential biomarker for the consumption of these foods.
CAS Number102-32-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.23 g/LALOGPS
logP0.93ALOGPS
logP1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability15.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O4
IUPAC name2-(3,4-dihydroxyphenyl)acetic acid
InChI IdentifierInChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
InChI KeyCFFZDZCDUFSOFZ-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=CC(O)=C(O)C=C1
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
Classification
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting Point168
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logP0.98SANGSTER (1994)
    Experimental pKa4.25
    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
    GC-MS3,4-Dihydroxyphenylacetic acid, 3 TMS, GC-MS Spectrumsplash10-004i-0942000000-54f714e694a7c3daeaf4Spectrum
    GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-004i-0931000000-c4bb79d921fb42cf1b40Spectrum
    GC-MS3,4-Dihydroxyphenylacetic acid, 3 TMS, GC-MS Spectrumsplash10-00di-9310000000-9490bd0ec921894341f4Spectrum
    GC-MS3,4-Dihydroxyphenylacetic acid, 3 TMS, GC-MS Spectrumsplash10-004i-0952000000-d45a1420d6ae61cb9169Spectrum
    GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-004i-0942000000-54f714e694a7c3daeaf4Spectrum
    GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-004i-0931000000-c4bb79d921fb42cf1b40Spectrum
    GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9310000000-9490bd0ec921894341f4Spectrum
    GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-004i-0952000000-d45a1420d6ae61cb9169Spectrum
    GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-004i-0931000000-3fab9c521f7f85372b94Spectrum
    Predicted GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3900000000-9badffe195f5e0ba98e0Spectrum
    Predicted GC-MS3,4-Dihydroxyphenylacetic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-4093000000-178e6eeb94df071e6c15Spectrum
    Predicted GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS3,4-Dihydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-709dd9faccdbbb3dc0882017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-cf69597350b36ab341992021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-298c198dac69afd9b0a32021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-ace1596cdfcf99646e9f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-0900000000-e7f718ad00bdba6675832021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-1900000000-d8334a99b44e227f0c592021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1900000000-72071b19a4bfa3da409d2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-3e7377f36ca2547f48852012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2900000000-60e1fc55d54131c2923e2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fi0-9400000000-c63542b296bac95866e22012-07-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a72015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb72015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d12015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-a59d2cab0d3d859760a72015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-1900000000-6f630370c11294562cb72015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9800000000-a45be46f3b52664dd4d12015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-aec26fe78ab78ddd40212021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-2900000000-e59402b8b36f408fbe1c2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9400000000-f36bad25ade880ae2e1f2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3a2015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b52015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b482015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-579796710abc38249c3a2015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0900000000-22f8a4f4efd0f10804b52015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zmi-9700000000-42b3de6bccbc10ad7b482015-05-27View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID532
    ChEMBL IDCHEMBL1284
    KEGG Compound IDC01161
    Pubchem Compound ID547
    Pubchem Substance IDNot Available
    ChEBI ID1386
    Phenol-Explorer ID572
    DrugBank IDDB01702
    HMDB IDHMDB01336
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDHOMOPROTOCATECHUIC-ACID|3,4-DIHYDROXYPHENYL-ACETATE
    BIGG ID36946
    KNApSAcK IDC00040996
    HET IDDHY
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia ID3,4-Dihydroxyphenylacetic_acid
    Phenol-Explorer Metabolite ID572
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    Pathways
    NameSMPDB LinkKEGG Link
    Tyrosine MetabolismSMP00006 map00350
    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).