Record Information
Version1.0
Creation date2010-04-08 22:08:15 UTC
Update date2020-04-21 18:03:26 UTC
Primary IDFDB008784
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-Cinnamic acid
DescriptionOccurs as free acid and esters in storax, Peruvian balsam and other resinsand is also present in tomato, pepper, red or white wine, porcini (Boletus edulis), peated malt, guava fruit, grapes, pineapple, raspberry, blackberry and other fruits. Flavouring agent Cinnamic acid is a white crystalline hydroxycinnamic acid, which is slightly soluble in water. It is obtained from oil of cinnamon, or from balsams such as storax. trans-Cinnamic acid is found in many foods, some of which are italian sweet red pepper, mushrooms, japanese pumpkin, and wax gourd.
CAS Number140-10-3
Structure
Thumb
Synonyms
SynonymSource
(2E)-3-Phenyl-2-propenoic acidChEBI
(2E)-3-Phenylacrylic acidChEBI
(e)-3-Phenyl-2-propenoic acidChEBI
(e)-CinnamateChEBI
(e)-Cinnamic acidChEBI
Benzeneacrylic acidChEBI
PHENYLETHYLENECARBOXYLIC ACIDChEBI
trans-3-Phenylacrylic acidChEBI
trans-beta-CarboxystyreneChEBI
trans-CinnamateChEBI
trans-ZimtsaeureChEBI
(2E)-3-Phenyl-2-propenoateGenerator
(2E)-3-PhenylacrylateGenerator
(e)-3-Phenyl-2-propenoateGenerator
BenzeneacrylateGenerator
PHENYLETHYLENECARBOXYLateGenerator
trans-3-PhenylacrylateGenerator
trans-b-CarboxystyreneGenerator
trans-Β-carboxystyreneGenerator
(2E)-2-Phenyl-2-propenoateHMDB
(2E)-2-Phenyl-2-propenoic acidHMDB
(e)-3-PhenylacrylateHMDB
(e)-3-Phenylacrylic acidHMDB
(e)-3-Phenylprop-2-enoateHMDB
(e)-3-Phenylprop-2-enoic acidHMDB
trans-3-Phenyl-2-propenoateHMDB
trans-3-Phenyl-2-propenoic acidHMDB
Cinnamic acid, 14C-labeled CPDHMDB
Cinnamic acid, 2-(14)C-labeled CPDHMDB
Cinnamic acid, 3-(14)C-labeled CPDHMDB
Cinnamic acid, (Z)-isomerHMDB
Cinnamic acid, 2-(13)C-labeled CPDHMDB
Cinnamic acid, 3H-labeled CPD (e)-isomerHMDB
Cinnamic acid, 3H-labeled CPD (Z)-isomerHMDB
Cinnamic acid, ion(1-)-(e)-isomerHMDB
Cinnamic acid, sodium saltHMDB
Cinnamic acid, sodium salt(e)-isomerHMDB
Cinnamic acid, sodium salt(Z)-isomerHMDB
Cinnamic acid, (trans)-(e)-isomerHMDB
Cinnamic acid, 14C-labeled CPD (e)-isomerHMDB
Cinnamic acid, ion(1-)HMDB
Cinnamic acid, nickel (+2) saltHMDB
Cinnamic acid, potassium saltHMDB
Cinnamic acid, zinc salt(e)-isomerHMDB
Cinnamic acid, 13C-labeled CPDHMDB
Cinnamic acidHMDB
(2E)-3-Phenylprop-2-enoic acidHMDB
(2E)-Cinnamic acidHMDB
3-Phenyl-(e)-2-propenoic acidHMDB
3-Phenyl-2-propenoic acidHMDB
3-Phenylacrylic acidHMDB
Phenylacrylic acidHMDB
beta-Phenylacrylic acidHMDB
Β-phenylacrylic acidHMDB
trans-Cinnamic acidHMDB
(2E)-3-Phenyl-2-Propenoic acidbiospider
(2e)-3-PhenylacrylateGenerator
(2e)-3-Phenylacrylic acidChEBI
(2E)-3-Phenylprop-2-enoatebiospider
(E)-3-Phenyl-2-propenoic acidbiospider
(E)-3-Phenylacrylatebiospider
(E)-3-Phenylacrylic acidbiospider
(E)-3-Phenylprop-2-enoatebiospider
(E)-3-Phenylprop-2-enoic acidbiospider
(E)-Cinnamatebiospider
(E)-Cinnamic acidbiospider
2-Propenoic acid, 3-phenyl-, (E)-biospider
Cinnamic acid, (E)-biospider
trans-β-Carboxystyrenebiospider
trans-β-carboxystyreneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H8O2
IUPAC name(2E)-3-phenylprop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
InChI KeyWBYWAXJHAXSJNI-VOTSOKGWSA-N
Isomeric SMILESOC(=O)\C=C\C1=CC=CC=C1
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
Classification
Description belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Styrene
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 72.96%; H 5.44%; O 21.60%DFC
Melting PointMp 133°DFC
Boiling PointBp 300°DFC
Experimental Water Solubility0.546 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.13HANSCH,C ET AL. (1995)
Experimental pKapKa 4.46 (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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0ue9-0910000000-4a7bcdfadd383bf577dcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0fb9-6920000000-727a2eb761e6e52fb47dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-117i-2920000000-f0d9ccc40786362ae4adJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ue9-0910000000-4a7bcdfadd383bf577dcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-6920000000-727a2eb761e6e52fb47dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-117i-2920000000-f0d9ccc40786362ae4adJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-2900000000-b105b3fcb63636d0d16fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5dJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-3107a2a1bec368528f82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ufr-6900000000-b0299d34fa9bb16b8258JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-4a879de8ea4f3acb0ae2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-88ad8c9c837a057bb2a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-18280fe18e43043d9e21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fb9-9600000000-04d36ba7639bc85e2023JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a8417274c4493c5b5871JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9100000000-d3712417826a69667981JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-37c486fa03918355413cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f6t-0900000000-218a5babf0ab7c31c498JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-88ad8c9c837a057bb2a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-e3a4fcaa911f14d3790dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-9600000000-04d36ba7639bc85e2023JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a8417274c4493c5b5871JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-d3712417826a69667981JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f6t-0900000000-218a5babf0ab7c31c498JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-f095c04fe81b2890cb1aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-1bb9599f57d5b1c1688bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-37c486fa03918355413cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-f5b771d960092fa83d2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-0900000000-58b4769b89ab3883fb05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6900000000-9f4710d90f0cafac6d7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-d015607beb5136324414JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-ff32add65ca52cbaae83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-3900000000-f2450299b70c3ec0faecJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0f6t-6900000000-77686ecc684f3b46bea6JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID392447
ChEMBL IDCHEMBL27246
KEGG Compound IDC10438
Pubchem Compound ID444539
Pubchem Substance IDNot Available
ChEBI ID15669
Phenol-Explorer ID549
DrugBank IDNot Available
HMDB IDHMDB00930
CRC / DFC (Dictionary of Food Compounds) IDHCV54-E:DXH18-D
EAFUS IDNot Available
Dr. Duke IDTRANS-CINNAMIC-ACID
BIGG IDNot Available
KNApSAcK IDC00000170
HET IDTCA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID140-10-3
GoodScent IDrw1003271
SuperScent IDNot Available
Wikipedia IDCinnamic_acid
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
Flavours
FlavorCitations
honey
  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
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
storax
  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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.