Record Information
Version1.0
Creation date2010-04-08 22:09:53 UTC
Update date2019-11-26 03:05:40 UTC
Primary IDFDB011887
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-(2-Hydroxyphenyl)propanoic acid
Description3-(2-Hydroxyphenyl)propanoic acid, also known as melilotic acid or melilotate, 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. 3-(2-Hydroxyphenyl)propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-(2-Hydroxyphenyl)propanoic acid exists in all living organisms, ranging from bacteria to humans. 3-(2-Hydroxyphenyl)propanoic acid has been detected, but not quantified in, several different foods, such as bilberries, chinese cinnamons, herbs and spices, pulses, and red beetroots. This could make 3-(2-hydroxyphenyl)propanoic acid a potential biomarker for the consumption of these foods.
CAS Number495-78-3
Structure
Thumb
Synonyms
SynonymSource
2-Hydroxybenzenepropanoic acidChEBI
3-(2-Hydroxyphenyl)propionic acidChEBI
3-(O-Hydroxyphenyl) propionic acidChEBI
Melilotic acidChEBI
O-Hydroxyphenylpropionic acidChEBI
2-HydroxyphenylpropanoateKegg
MelilotateKegg
3-(2-Hydroxyphenyl)propionateKegg
2-HydroxybenzenepropanoateGenerator
3-(O-Hydroxyphenyl) propionateGenerator
O-HydroxyphenylpropionateGenerator
2-Hydroxyphenylpropanoic acidGenerator
3-(2-Hydroxyphenyl)propanoateGenerator
2-Hydroxy-benzenepropanoic acidHMDB
2-Hydroxybenzenepropanoic acid, 9ciHMDB
3-(2-Hydroxyphenyl) propanoic acidHMDB
3-(2-Hydroxyphenyl) propionateHMDB
3-(O-Hydroxyphenyl)propionic acid, 8ciHMDB
beta -(O-Hydroxyphenyl)propionic acidHMDB
beta-(O-Hydroxyphenyl)propionic acidHMDB
Hydrocoumaric acidHMDB
O-Hydroxyhydrocinnamic acidHMDB
OHPAMeSH
Ortho-hydroxyphenylpropionic acidMeSH
β-(o-hydroxyphenyl)propionic acidbiospider
2-hydroxybenzenepropanoic acidbiospider
2-Hydroxybenzenepropanoic acid, 9CIdb_source
3-(o-Hydroxyphenyl) propionic acidbiospider
3-(o-Hydroxyphenyl)propionic acid, 8CIdb_source
Benzenepropanoic acid, 2-hydroxy-biospider
Beta-(o-hydroxyphenyl)propionic acidbiospider
o-Hydroxyhydrocinnamic aciddb_source
O-hydroxyphenylpropionic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility2.76 g/LALOGPS
logP1.12ALOGPS
logP1.75ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
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
Polarizability16.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H10O3
IUPAC name3-(2-hydroxyphenyl)propanoic acid
InChI IdentifierInChI=1S/C9H10O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-4,10H,5-6H2,(H,11,12)
InChI KeyCJBDUOMQLFKVQC-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCC1=CC=CC=C1O
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-4-unsubstituted benzenoid
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.05%; H 6.07%; O 28.88%DFC
Melting PointMp 82-83°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa1 4.75 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-01r6-1920000000-ecd488078d5985eafbfbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-01r6-1920000000-ecd488078d5985eafbfbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-b8cabfe5c488ee1ed604JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3900000000-58936d8a48b093519ddfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00g0-9660000000-6b8bf956c80314489670JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-9be30b68ac3a0ad3df6eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-0dbababdf59aa8829b0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05fr-0900000000-168a901fccbb4f1968d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-1900000000-d8ea269e67bd24e633aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-5900000000-337a9131168ae129bf9eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-43f2a467bcbee742fee2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-5cf8803d756201d8053aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-2900000000-6784db2a14b98ff73d39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9300000000-20e163ee7cf68d1903d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-03d3c3e2a1e37e56c664JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-1aab1942696c4a143efbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-e8222e98d8f7bc4e7bdeJSpectraViewer
ChemSpider ID850
ChEMBL IDNot Available
KEGG Compound IDC01198
Pubchem Compound ID873
Pubchem Substance IDNot Available
ChEBI ID16104
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33752
CRC / DFC (Dictionary of Food Compounds) IDHBN89-X:HBN89-X
EAFUS IDNot Available
Dr. Duke IDMELILOTIC-ACID
BIGG IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
anti ulcerogenic49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
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).