Record Information
Version1.0
Creation date2010-04-08 22:08:00 UTC
Update date2018-01-23 19:02:26 UTC
Primary IDFDB008271
Secondary Accession Numbers
  • FDB030691
Chemical Information
FooDB Name3-Phenylpropanoic acid
DescriptionHydrocinnamic acid is an analogue of phenylalanine. It is a substrate of the enzyme oxidoreductases [EC 1.14.12.-] in the pathway phenylalanine metabolism (KEGG). 3-Phenylpropanoic acid is found in many foods, some of which are purple laver, quinoa, custard apple, and conch.
CAS Number501-52-0
Structure
Thumb
Synonyms
SynonymSource
3-Phenyl-propionic acidChEBI
3-Phenylpropanoic acidChEBI
3-PhenylpropionsaeureChEBI
3PPChEBI
Benzenepropanoic acidChEBI
Benzenepropionic acidChEBI
Benzylacetic acidChEBI
beta-Phenylpropionic acidChEBI
Dihydrocinnamic acidChEBI
HydrozimtsaeureChEBI
PhenylpropanoateChEBI
3-Phenylpropionic acidKegg
3-Phenyl-propionateGenerator
3-PhenylpropanoateGenerator
BenzenepropanoateGenerator
BenzenepropionateGenerator
BenzylacetateGenerator
b-PhenylpropionateGenerator
b-Phenylpropionic acidGenerator
beta-PhenylpropionateGenerator
Β-phenylpropionateGenerator
Β-phenylpropionic acidGenerator
DihydrocinnamateGenerator
Phenylpropanoic acidGenerator
3-PhenylpropionateGenerator
HydrocinnamateGenerator
3-Phenyl-N-propionateHMDB
3-Phenyl-N-propionic acidHMDB
Omega-phenylpropanoateHMDB
Omega-phenylpropanoic acidHMDB
W-PhenylpropanoateHMDB
W-Phenylpropanoic acidHMDB
3-Phenylpropionic acid, sodium saltHMDB
3-Phenyl propionic acidHMDB
HYDROCINNAMIC ACIDChEBI
Phenylpropionic acidHMDB
beta-Phenylpropanoic acidHMDB
β-Phenylpropanoic acidHMDB
ω-Phenylpropanoic acidHMDB
Benzenepropanoic acid, 9CIdb_source
beta-Phenylpropioic acidbiospider
Homotoluic aciddb_source
Hydrocinnamic aciddb_source
omega-Phenylpropanoatebiospider
omega-Phenylpropanoic acidbiospider
Phenyl propionic acidbiospider
w-Phenylpropanoatebiospider
w-Phenylpropanoic acidbiospider
β-phenylpropionateGenerator
β-phenylpropionic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility1.7 g/LALOGPS
logP1.84ALOGPS
logP2.06ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.97 m³·mol⁻¹ChemAxon
Polarizability15.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H10O2
IUPAC name3-phenylpropanoic acid
InChI IdentifierInChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)
InChI KeyXMIIGOLPHOKFCH-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCC1=CC=CC=C1
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
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
  • 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
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 71.98%; H 6.71%; O 21.31%DFC
Melting PointMp 48.5°DFC
Boiling PointBp6 125-129°DFC
Experimental Water Solubility5.9 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.84HANSCH,C ET AL. (1995)
Experimental pKapKa 4.66 (H2O)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-1920000000-829ee511cbcb511eaa0dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-6910000000-1df0ef2a35aedd93b1f0View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9600000000-685b73e7f17a8be64f76View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9400000000-6b08d11fe7d8828ea0b4View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0900000000-271b64525610b577f87cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9300000000-faf8506e70502be88599View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6x-9800000000-6d3e3634b1663556c431View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-1940000000-4bdbde45f0dac2b3ec59View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1920000000-829ee511cbcb511eaa0dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-6910000000-1df0ef2a35aedd93b1f0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-2910000000-b14f8ca2c631d87eb834View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-8900000000-bbfe334bf7c6f8fab3edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0596-9510000000-32f6cb9988fbfb2c022eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-60af9a7ac23f78383156View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-9009f92e094d3f88cea0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-1009c57a9a26d3fd03a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udl-9600000000-f55343cc6dbf913455ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0006-9400000000-6b08d11fe7d8828ea0b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (JEOL JMS-D-300) , Positivesplash10-0udi-0900000000-271b64525610b577f87cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0udl-9300000000-0b08772b626dd7c66febView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-56bd4f79b41d2e676de8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052b-2900000000-b4b013241fad936a6040View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9100000000-21973848f978136e5896View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID10181339
ChEMBL IDCHEMBL851
KEGG Compound IDC05629
Pubchem Compound ID107
Pubchem Substance IDNot Available
ChEBI ID28631
Phenol-Explorer ID975
DrugBank IDDB02024
HMDB IDHMDB00764
CRC / DFC (Dictionary of Food Compounds) IDDFK03-O:DFK03-O
EAFUS ID3020
Dr. Duke IDDIHYDROCINNAMIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDHCI
Flavornet ID501-52-0
GoodScent IDrw1020511
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID975
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
Flavours
FlavorCitations
balsamic
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musk
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cinnamon
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).