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Showing Compound 2-Hydroxyphenylacetic acid (FDB012331)

Record Information
Version1.0
Creation date2010-04-08 22:10:07 UTC
Update date2019-11-26 03:06:35 UTC
Primary IDFDB012331
Secondary Accession Numbers
  • FDB030339
Chemical Information
FooDB Name2-Hydroxyphenylacetic acid
Descriptionortho-Hydroxyphenylacetic acid, also known as (O-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. ortho-Hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. ortho-Hydroxyphenylacetic acid has been detected, but not quantified in, several different foods, such as sweet cherries (Prunus avium), elliott's blueberries (Vaccinium elliottii), malabar spinaches (Basella alba), dandelions (Taraxacum officinale), and grapefruit/pummelo hybrids (Citrus paradisi X Citrus maxima). This could make ortho-hydroxyphenylacetic acid a potential biomarker for the consumption of these foods. ortho-Hydroxyphenylacetic acid, with regard to humans, has been found to be associated with several diseases such as irritable bowel syndrome and eosinophilic esophagitis; ortho-hydroxyphenylacetic acid has also been linked to the inborn metabolic disorder phenylketonuria. Based on a literature review a significant number of articles have been published on ortho-Hydroxyphenylacetic acid.
CAS Number614-75-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(O-Hydroxyphenyl)acetic acidChEBI
2'-Hydroxyphenylacetic acidChEBI
2-Hydroxybenzeneacetic acidChEBI
2-Hydroxyphenylacetic acidChEBI
O-Hydroxyphenylacetic acidChEBI
(O-Hydroxyphenyl)acetateGenerator
2'-HydroxyphenylacetateGenerator
2-HydroxybenzeneacetateGenerator
2-HydroxyphenylacetateGenerator
O-HydroxyphenylacetateGenerator
Ortho-hydroxyphenylacetateGenerator
(2-Hydroxyphenyl)acetateHMDB
(2-Hydroxyphenyl)acetic acidHMDB
(O-Hydroxyphenyl)-acetateHMDB
(O-Hydroxyphenyl)-acetic acidHMDB
2-HPAAHMDB
HydroxyphenylacetateHMDB
Hydroxyphenylacetic acidHMDB
O-Hydroxyphenyl acetic acidHMDB
Ortho-hydroxyphenylacetic acidMeSH
2-Hydroxybenzeneacetic acid, 9CIdb_source
o-Hydroxy-a-toluic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility6.38 g/LALOGPS
logP0.99ALOGPS
logP1.31ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O3
IUPAC name2-(2-hydroxyphenyl)acetic acid
InChI IdentifierInChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyCCVYRRGZDBSHFU-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=CC=CC=C1O
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
Classification
Description Belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acids
Direct Parent2(hydroxyphenyl)acetic acids
Alternative Parents
Substituents
  • 2(hydroxyphenyl)acetic acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 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
Disposition

Route of exposure:

Biological location:

Source:

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 stateLiquid
    Physical DescriptionNot Available
    Mass CompositionC 63.15%; H 5.30%; O 31.55%DFC
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    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-MS2-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-ca3851c9928227913a97Spectrum
    GC-MS2-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrumsplash10-0w29-1970000000-de8569a7d279b97680a4Spectrum
    GC-MS2-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0960000000-1018d2254ff44190f41aSpectrum
    GC-MS2-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-ca3851c9928227913a97Spectrum
    GC-MS2-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0w29-1970000000-de8569a7d279b97680a4Spectrum
    Predicted GC-MS2-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1900000000-0a090cff04cd89d36022Spectrum
    Predicted GC-MS2-Hydroxyphenylacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6930000000-1903392fd44f061e93ebSpectrum
    Predicted GC-MS2-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS2-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS2-Hydroxyphenylacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS2-Hydroxyphenylacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS2-Hydroxyphenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS2-Hydroxyphenylacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS2-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-c0378212353f9c2470602012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0900000000-2e1d10888e4b882683d42012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-1900000000-87d962f7cd6aa06c48322012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0900000000-e7c99cfd03a6c025cf2c2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0900000000-e7c99cfd03a6c025cf2c2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-69f9fe8670d9a6ce3b782021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-77bc386fb6ce14ec2dd12021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-7fb7c81915195d1050782021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-8f1c3458a31199029d712021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-5900000000-b7dfc901d3e6c4db398b2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-e31e91ce81a098f179442021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-e7bfeba3bf5179c0cbfb2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-0c76ffcb76d341ed2f1d2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-7900000000-1b46df694de9c5dd84ca2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-81d25cd8f42ea4104dc92021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-4ad240d4583d43a1ec3e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-bd8c8286e031da5cb96c2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-8900000000-1c3e198c05d77bf0541f2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-17130a549d9e41fac3f62021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-6a2b0b911cb357174c272017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-06436376438e44718bb72017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9300000000-19f4bd2f314d6c0b49bd2017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-c00a2e1956529eb24b432017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-0900000000-a60511b0d006628958712017-09-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-4900000000-68a51d2b15b093ce15452017-09-01View Spectrum
    NMR
    TypeDescriptionView
    1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, 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, 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
    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, 400 MHz, H2O, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID11476
    ChEMBL IDCHEMBL240714
    KEGG Compound IDC05852
    Pubchem Compound ID11970
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID953
    DrugBank IDNot Available
    HMDB IDHMDB00669
    CRC / DFC (Dictionary of Food Compounds) IDHGJ50-U:HGJ50-U
    EAFUS IDNot Available
    Dr. Duke IDO-HYDROXYPHENYLACETIC-ACID
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDOHP
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID953
    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
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).