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3-Phenylpropanoic acid (FDB008271)

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 3-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 exists in all living organisms, ranging from bacteria to humans. Hydrocinnamic acid is a sweet, balsamic, and cinnamon tasting compound. Hydrocinnamic acid is found, on average, in the highest concentration within beer. Hydrocinnamic acid has also been detected, but not quantified in, several different foods, such as garden tomato (var.), winter savories (Satureja montana), naranjillas (Solanum quitoense), rowanberries (Sorbus aucuparia), and european cranberries (Vaccinium oxycoccos). This could make hydrocinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Hydrocinnamic acid.
CAS Number501-52-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.7 g/LALOGPS
logP1.84ALOGPS
logP2.06ChemAxon
logS-2ALOGPS
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1920000000-829ee511cbcb511eaa0dSpectrum
GC-MS3-Phenylpropanoic acid, 1 TMS, GC-MS Spectrumsplash10-0udi-6910000000-1df0ef2a35aedd93b1f0Spectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udl-9600000000-685b73e7f17a8be64f76Spectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9400000000-6b08d11fe7d8828ea0b4Spectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0900000000-271b64525610b577f87cSpectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udl-9300000000-faf8506e70502be88599Spectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0f6x-9800000000-6d3e3634b1663556c431Spectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1940000000-4bdbde45f0dac2b3ec59Spectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1920000000-829ee511cbcb511eaa0dSpectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-6910000000-1df0ef2a35aedd93b1f0Spectrum
GC-MS3-Phenylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-2910000000-b14f8ca2c631d87eb834Spectrum
Predicted GC-MS3-Phenylpropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f6x-8900000000-bbfe334bf7c6f8fab3edSpectrum
Predicted GC-MS3-Phenylpropanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0596-9510000000-32f6cb9988fbfb2c022eSpectrum
Predicted GC-MS3-Phenylpropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Phenylpropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Phenylpropanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-56bd4f79b41d2e676de82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052b-2900000000-b4b013241fad936a60402012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9100000000-21973848f978136e58962012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06e2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00dj-0229210000-3bd038d0275527aaf06e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-56bd4f79b41d2e676de82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052b-2900000000-b4b013241fad936a60402017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9100000000-21973848f978136e58962017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0900000000-b8bb01617b312682874b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-5d1cbf0e902fef2a674d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-60af9a7ac23f783831562012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-9009f92e094d3f88cea02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-1009c57a9a26d3fd03a12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udl-9600000000-f55343cc6dbf913455ec2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0006-9400000000-6b08d11fe7d8828ea0b42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CI-B (JEOL JMS-D-300) , Positivesplash10-0udi-0900000000-271b64525610b577f87c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0udl-9300000000-0b08772b626dd7c66feb2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de012015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ce2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd5375468372596922015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de012015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ce2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd5375468372596922015-05-27View 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 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).