Record Information
Version1.0
Creation date2010-04-08 22:08:00 UTC
Update date2019-11-26 03:02:22 UTC
Primary IDFDB008271
Secondary Accession Numbers
  • FDB030691
Chemical Information
FooDB Name3-Phenylpropanoic acid
DescriptionHydrocinnamic acid, also known as phenylpropanoate or dihydrocinnamate, 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. Hydrocinnamic acid is a weakly acidic compound (based on its pKa). Hydrocinnamic acid exists in all living organisms, ranging from bacteria to humans. Hydrocinnamic acid is a sweet, balsamic, and cinnamon tasting compound. Hydrocinnamic acid has been detected, but not quantified in, several different foods, such as sago palms, roselles, tree ferns, yellow zucchinis, and other cereal products. This could make hydrocinnamic acid a potential biomarker for the consumption of these foods.
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
Phenylpropionic acidHMDB
beta-Phenylpropanoic acidHMDB
Β-phenylpropanoic acidHMDB
Ω-phenylpropanoic acidHMDB
HYDROCINNAMIC ACIDChEBI
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
BioavailabilityYesChemAxon
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-1920000000-829ee511cbcb511eaa0dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-6910000000-1df0ef2a35aedd93b1f0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9600000000-685b73e7f17a8be64f76JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9400000000-6b08d11fe7d8828ea0b4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0900000000-271b64525610b577f87cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-9300000000-faf8506e70502be88599JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6x-9800000000-6d3e3634b1663556c431JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-1940000000-4bdbde45f0dac2b3ec59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1920000000-829ee511cbcb511eaa0dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-6910000000-1df0ef2a35aedd93b1f0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-2910000000-b14f8ca2c631d87eb834JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-8900000000-bbfe334bf7c6f8fab3edJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0596-9510000000-32f6cb9988fbfb2c022eJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-60af9a7ac23f78383156JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-9009f92e094d3f88cea0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-1009c57a9a26d3fd03a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udl-9600000000-f55343cc6dbf913455ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0006-9400000000-6b08d11fe7d8828ea0b4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (JEOL JMS-D-300) , Positivesplash10-0udi-0900000000-271b64525610b577f87cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0udl-9300000000-0b08772b626dd7c66febJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-56bd4f79b41d2e676de8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052b-2900000000-b4b013241fad936a6040JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9100000000-21973848f978136e5896JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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).