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Showing Compound 2-Hydroxyphloretic acid (FDB019021)

Record Information
Version1.0
Creation date2010-04-08 22:14:05 UTC
Update date2019-11-26 03:16:59 UTC
Primary IDFDB019021
Secondary Accession Numbers
  • FDB017136
Chemical Information
FooDB Name2-Hydroxyphloretic acid
DescriptionHydroxyphenyllactic acid, also known as 4-hydroxyphenyllactate or HPLA, 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. Hydroxyphenyllactic acid exists in all eukaryotes, ranging from yeast to plants to humans. Hydroxyphenyllactic acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), breakfast cereal, cereals and cereal products, chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make hydroxyphenyllactic acid a potential biomarker for the consumption of these foods. Hydroxyphenyllactic acid, with regard to humans, has been found to be associated with several diseases such as supragingival plaque, colorectal cancer, and eosinophilic esophagitis; hydroxyphenyllactic 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 Hydroxyphenyllactic acid.
CAS Number306-23-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Hydroxy-3-(4-hydroxyphenyl)propanoateChEBI
2-Hydroxy-3-(p-hydroxyphenyl)propionic acidChEBI
4-Hydroxyphenyllactic acidChEBI
beta-(4-Hydroxyphenyl)lactic acidChEBI
beta-(p-Hydroxyphenyl)lactic acidChEBI
DL-p-Hydroxyphenyllactic acidChEBI
p-Hydroxyphenyl lactic acidChEBI
4-HydroxyphenyllactateKegg
p-HydroxyphenyllactateKegg
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acidGenerator
2-Hydroxy-3-(p-hydroxyphenyl)propionateGenerator
b-(4-Hydroxyphenyl)lactateGenerator
b-(4-Hydroxyphenyl)lactic acidGenerator
beta-(4-Hydroxyphenyl)lactateGenerator
Β-(4-hydroxyphenyl)lactateGenerator
Β-(4-hydroxyphenyl)lactic acidGenerator
b-(p-Hydroxyphenyl)lactateGenerator
b-(p-Hydroxyphenyl)lactic acidGenerator
beta-(p-Hydroxyphenyl)lactateGenerator
Β-(p-hydroxyphenyl)lactateGenerator
Β-(p-hydroxyphenyl)lactic acidGenerator
DL-p-HydroxyphenyllactateGenerator
p-Hydroxyphenyl lactateGenerator
p-Hydroxyphenyllactic acidGenerator
HydroxyphenyllactateGenerator
(RS)-3-(4-Hydroxyphenyl)lactateHMDB
(RS)-3-(4-Hydroxyphenyl)lactic acidHMDB
3-(4-Hydroxyphenyl)-DL-lactateHMDB
3-(4-Hydroxyphenyl)-DL-lactic acidHMDB
3-(4-Hydroxyphenyl)lactateHMDB
3-(p-Hydroxyphenyl)-lactateHMDB
3-(p-Hydroxyphenyl)-lactic acidHMDB
a,4-DihydroxybenzenepropanoateHMDB
a,4-Dihydroxybenzenepropanoic acidHMDB
b-(p-Hydroxyphenyl)-DL-lactateHMDB
b-(p-Hydroxyphenyl)-DL-lactic acidHMDB
beta-(p-Hydroxyphenyl)-DL-lactateHMDB
beta-(p-Hydroxyphenyl)-DL-lactic acidHMDB
DL-3-(4-Hydroxyphenyl)lactateHMDB
DL-3-(4-Hydroxyphenyl)lactic acidHMDB
HPLAHMDB
4-Hydroxyphenyllactic acid, (DL)-isomerHMDB
Para-hydroxyphenyllactic acidHMDB
2-HydroxyphloretateHMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acidHMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid HMDB
(RS)-3-(4-hydroxyphenyl)lactateHMDB
(RS)-3-(4-hydroxyphenyl)lactic acidHMDB
2-Hydroxy-3-(P-hydroxyphenyl)propionateGenerator
2-Hydroxy-3-(P-hydroxyphenyl)propionic acidChEBI
2-Hydroxyphloretic acidmanual
3-(4-Hydroxyphenyl)lactic acidHMDB
3-(4-Hydroxyphenyl)lactic acid, 8CIdb_source
3-(P-Hydroxyphenyl)-lactateHMDB
3-(P-Hydroxyphenyl)-lactic acidHMDB
a,4-Dihydroxybenzenepropanoic acid, 9CIdb_source
b-(P-Hydroxyphenyl)-DL-lactateHMDB
b-(P-Hydroxyphenyl)-DL-lactic acidHMDB
b-(P-Hydroxyphenyl)lactateGenerator
b-(P-Hydroxyphenyl)lactic acidGenerator
beta-(P-Hydroxyphenyl)-DL-lactateHMDB
beta-(P-Hydroxyphenyl)-DL-lactic acidHMDB
beta-(P-Hydroxyphenyl)lactateGenerator
beta-(P-Hydroxyphenyl)lactic acidChEBI
DL-P-HydroxyphenyllactateGenerator
DL-P-Hydroxyphenyllactic acidChEBI
P-Hydroxyphenyl lactateGenerator
P-Hydroxyphenyl lactic acidChEBI
β-(4-hydroxyphenyl)lactateGenerator
β-(4-hydroxyphenyl)lactic acidGenerator
β-(P-hydroxyphenyl)lactateGenerator
β-(P-hydroxyphenyl)lactic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility4.79 g/LALOGPS
logP0.87ALOGPS
logP0.88ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.44 m³·mol⁻¹ChemAxon
Polarizability17.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O4
IUPAC name2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
InChI IdentifierInChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
InChI KeyJVGVDSSUAVXRDY-UHFFFAOYSA-N
Isomeric SMILESOC(CC1=CC=C(O)C=C1)C(O)=O
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
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
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 59.34%; H 5.53%; O 35.13%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-MSxi-2-Hydroxyphloretic acid, 3 TMS, GC-MS Spectrumsplash10-004i-1911000000-424dc0a114976e4a6052Spectrum
GC-MSxi-2-Hydroxyphloretic acid, non-derivatized, GC-MS Spectrumsplash10-004i-1911000000-424dc0a114976e4a6052Spectrum
GC-MSxi-2-Hydroxyphloretic acid, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-b7f0ddb24f5c187d4540Spectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-3900000000-aece5a68ba54ab74c5eeSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003r-5496000000-fbb65d0c963e70625e95Spectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSxi-2-Hydroxyphloretic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00li-2900000000-ea59f9dcf58b55bec6ca2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-054n-9300000000-5b39aa5183630ccd7f4d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0k92-9200000000-c698fdbe1eefac6e9eab2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01qi-0900000000-640a5a477752571a14432012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03di-0900000000-45b5f23bae1a9641fb0b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01qi-0900000000-640a5a477752571a14432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-03ei-0900000000-d89828d3625adabd215b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00ou-9000000000-60dd6237cac5c79c75082021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00ri-2900000000-69365cb4d9937f6a96e02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00li-1900000000-03a7d2e8f219eba66eee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-029i-0900000000-fd70bef080a1a354df5a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9400000000-65da3c598368dbad66cd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-052b-9100000000-6ad54b488ac0183ff4bf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9400000000-af41107b1e7be38f765c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-023a994f4d18e32123cd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-5900000000-8fcf87adaaae828f3aae2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00ri-2900000000-ed974245d122fcbc31c02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03ei-1900000000-fd1d5ff4f32cdcdf0a382021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00ec-9400000000-9b26dc9e6bb4e1a72cfb2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05o9-0900000000-a343595d5c411e940c252016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0900000000-1f777ab6b9486c1813552016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9800000000-db82c9bf8afdb32af6de2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-3e1a7023e9214816e8a52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-2900000000-c05e995d8c57a180bae72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mx-9800000000-729b43ad9499a14c2d012016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 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 ID9010
ChEMBL IDCHEMBL1162489
KEGG Compound IDC03672
Pubchem Compound ID9378
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID577
DrugBank IDNot Available
HMDB IDHMDB00755
CRC / DFC (Dictionary of Food Compounds) IDLNP81-X:LNP81-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2392410
KNApSAcK IDNot Available
HET IDNot Available
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference