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Showing Compound Phloretic acid (FDB000849)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2024-11-29 22:26:58 UTC
Primary IDFDB000849
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhloretic acid
DescriptionDesaminotyrosine, also known as phloretinic acid or dihydro-p-coumarate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Desaminotyrosine is found, on average, in the highest concentration within olives (Olea europaea) and beer. Desaminotyrosine has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), peanuts (Arachis hypogaea), chickens (Gallus gallus), avocados (Persea americana), and domestic pigs (Sus scrofa domestica). This could make desaminotyrosine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Desaminotyrosine.
CAS Number501-97-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-(p-Hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenylpropionic acidChEBI
beta-(p-Hydroxyphenyl)propionic acidChEBI
Dihydro-p-coumaric acidChEBI
HYDROXYPHENYL propionIC ACIDChEBI
p-Hydroxyhydrocinnamic acidChEBI
p-Hydroxyphenylpropionic acidChEBI
Phloretinic acidChEBI
3-(4-Hydroxyphenyl)propanoateKegg
3-(4-Hydroxyphenyl)propionateGenerator
3-(p-Hydroxyphenyl)propionateGenerator
4-HydroxyphenylpropionateGenerator
b-(p-Hydroxyphenyl)propionateGenerator
b-(p-Hydroxyphenyl)propionic acidGenerator
beta-(p-Hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionateGenerator
Β-(p-hydroxyphenyl)propionic acidGenerator
Dihydro-p-coumarateGenerator
HYDROXYPHENYL propionateGenerator
p-HydroxyhydrocinnamateGenerator
p-HydroxyphenylpropionateGenerator
PhloretinateGenerator
PhloretateGenerator
3-(4-Hydroxyphenyl)propanoic acidGenerator
3-(4'-Hydroxyphenyl)-propionateHMDB
3-(4'-Hydroxyphenyl)-propionic acidHMDB
3-(4'-Hydroxyphenyl)propionic acidHMDB
3-(4-Hydroxy-phenyl)-propionateHMDB
3-(4-Hydroxy-phenyl)-propionic acidHMDB
3-(4-Hydroxyphenyl)-propionateHMDB
3-(4-Hydroxyphenyl)-propionic acidHMDB
3-(Para-hydroxyphenyl)propionateHMDB
3-(Para-hydroxyphenyl)propionic acidHMDB
4'-Hydroxyphenylpropionic acidHMDB
4-(4-HydroxyphenylpropanoateHMDB
4-(4-Hydroxyphenylpropanoic acidHMDB
4-Hydroxy-(9ci)benzenepropanoateHMDB
4-Hydroxy-(9ci)benzenepropanoic acidHMDB
4-Hydroxy-benzenepropanoateHMDB
4-Hydroxy-benzenepropanoic acidHMDB
4-HydroxybenzenepropanoateHMDB
4-Hydroxybenzenepropanoic acidHMDB
hydro-P-CoumarateHMDB
Hydro-p-coumaric acidHMDB
Hydroxy-hydrocinnamic acidHMDB
N-Hydroxysuccinimide esterHMDB
P-Hydroxy-benzene propionateHMDB
P-Hydroxy-benzene propionic acidHMDB
P-Hydroxy-hydrocinnamateHMDB
P-Hydroxy-hydrocinnamic acidHMDB
4-Hydroxyhydrocinnamic acidMeSH, HMDB
DesaminotyrosineChEBI
3-(4'-Hydroxyphenyl)propanoic acidPhytoBank
4-Hydroxybenzenepropionic acidPhytoBank
2,3-Dihydro-p-coumaric acidPhytoBank
3-(4’-Hydroxyphenyl)propanoic acidPhytoBank
3-(4’-Hydroxyphenyl)propionic acidPhytoBank
3-(p-Hydroxyphenyl)propanoic acidPhytoBank
4-(2-Carboxyethyl)phenolPhytoBank
4-(2-Carboxylethyl)phenolPhytoBank
4-Hydroxydihydrocinnamic acidPhytoBank
Dihydrocoumaric acidPhytoBank
p-Hydroxybenzene propanoic acidPhytoBank
p-Hydroxybenzene propionic acidPhytoBank
p-Hydroxyphenylpropanoic acidPhytoBank
beta-(4-Hydroxyphenyl)propanoic acidPhytoBank
beta-(4-Hydroxyphenyl)propionic acidPhytoBank
β-(4-Hydroxyphenyl)propanoic acidPhytoBank
β-(4-Hydroxyphenyl)propionic acidPhytoBank
beta-(p-Hydroxyphenyl)propanoic acidPhytoBank
β-(p-Hydroxyphenyl)propanoic acidPhytoBank
3-(4-hydroxyphenyl)propionatemanual
3-(4-Hydroxyphenyl)propionic acidmanual
3-(P-Hydroxyphenyl)propionic acidChEBI
3-(p-Hydroxyphenyl)propionic acid, 8CIdb_source
4-Hydroxybenzenepropanoic acid, 9CIdb_source
b-(P-Hydroxyphenyl)propionateGenerator
b-(P-Hydroxyphenyl)propionic acidGenerator
beta-(P-Hydroxyphenyl)propionateGenerator
beta-(P-Hydroxyphenyl)propionic acidChEBI
dihydro-P-CoumarateGenerator
HPPAdb_source
hydro-P-Coumaric acidHMDB
P-HydroxyhydrocinnamateGenerator
P-HydroxyphenylpropionateGenerator
P-Hydroxyphenylpropionic acidChEBI
Phloretic aciddb_source
β-(P-hydroxyphenyl)propionateGenerator
β-(P-hydroxyphenyl)propionic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility2.71 g/LALOGPS
logP1.15ALOGPS
logP1.75ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability16.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O3
IUPAC name3-(4-hydroxyphenyl)propanoic acid
InChI IdentifierInChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
InChI KeyNMHMNPHRMNGLLB-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCC1=CC=C(O)C=C1
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
Classification
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 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:

Biological role:

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 CompositionC 65.05%; H 6.07%; O 28.88%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-MSPhloretic acid, non-derivatized, GC-MS Spectrumsplash10-066r-9800000000-44e113d8fc2602ffba88Spectrum
    GC-MSPhloretic acid, non-derivatized, GC-MS Spectrumsplash10-004l-0900000000-5ae3f727b5218398aa83Spectrum
    GC-MSPhloretic acid, non-derivatized, GC-MS Spectrumsplash10-066r-9800000000-44e113d8fc2602ffba88Spectrum
    GC-MSPhloretic acid, non-derivatized, GC-MS Spectrumsplash10-004l-0900000000-5ae3f727b5218398aa83Spectrum
    Predicted GC-MSPhloretic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-3900000000-424e95de0b8037c4aa20Spectrum
    Predicted GC-MSPhloretic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00g0-9660000000-261dcfd72b0dbd1c03dfSpectrum
    Predicted GC-MSPhloretic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kv-5900000000-db98339dadc21116c7aa2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052r-9400000000-7d2340d4f6981ee8aecb2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00bi-9100000000-cac6ca239c2cbe36238d2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-e131522c5a7352167afb2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-3900000000-5c5920f4693d31baa6402012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9500000000-49bd07916272cdc49e682012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a6u-9100000000-683b03c9384a9a7508632012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-d4af6cba1b370fd620ed2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-514be816ed648e5588b72017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5c5920f4693d31baa6402017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9500000000-49bd07916272cdc49e682017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6u-9100000000-683b03c9384a9a7508632017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-d4af6cba1b370fd620ed2017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-3603746465916eaf1e982017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0601-1900000000-a85683e512fff2c291dd2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdi-9500000000-dbb0fa659379ccf4eb262017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-17bb794e8bbfe1aad6b32017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-9708817125183e0214a32017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-d9a164ed2938481885d92017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-5900000000-6672a989c0ad56cb16972021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fu-8900000000-f2a5c52c26b284a94a512021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-179e6648decb5dd319532021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aba-0900000000-3631ad60fd3a5053aacf2021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-28c2e194d667a26ec1522021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9300000000-20c3b533b0eccb02601e2021-09-24View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID9965
    ChEMBL IDCHEMBL1172560
    KEGG Compound IDC01744
    Pubchem Compound ID10394
    Pubchem Substance IDNot Available
    ChEBI ID32980
    Phenol-Explorer ID578
    DrugBank IDDB03897
    HMDB IDHMDB02199
    CRC / DFC (Dictionary of Food Compounds) IDBJT98-T:BJT98-T
    EAFUS IDNot Available
    Dr. Duke IDPHLORETIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00029471
    HET IDHPP
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    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
    Metabolsim and Physiological Effects of 4-EthylphenylsulfateSMP0125541 Not Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    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).
    — 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.
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.