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trans-cinnamate (FDB031209)

Record Information
Version1.0
Creation date2015-05-07 21:19:50 UTC
Update date2019-11-26 03:22:11 UTC
Primary IDFDB031209
Secondary Accession Numbers
  • FDB008784
Chemical Information
FooDB Nametrans-cinnamate
DescriptionTrans-cinnamic acid, also known as (2e)-3-phenyl-2-propenoic acid or (E)-cinnamate, is a member of the class of compounds known as cinnamic acids. Cinnamic acids are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Trans-cinnamic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Trans-cinnamic acid is a sweet, balsam, and honey tasting compound and can be found in a number of food items such as maitake, mustard spinach, common wheat, and barley, which makes trans-cinnamic acid a potential biomarker for the consumption of these food products. Trans-cinnamic acid can be found primarily in saliva. Trans-cinnamic acid exists in all living species, ranging from bacteria to humans. Trans-cinnamic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cinnamic acid is an organic compound with the formula C6H5CHCHCO2H. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common .
CAS Number621-82-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
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
EI-MSMass Spectrum (Electron Ionization)splash10-0f6t-6900000000-77686ecc684f3b46bea62014-09-20View Spectrum
GC-MStrans-Cinnamic acid, 1 TMS, GC-MS Spectrumsplash10-0ue9-0910000000-4a7bcdfadd383bf577dcSpectrum
GC-MStrans-Cinnamic acid, 1 TMS, GC-MS Spectrumsplash10-0fb9-6920000000-727a2eb761e6e52fb47dSpectrum
GC-MStrans-Cinnamic acid, 1 TMS, GC-MS Spectrumsplash10-117i-2920000000-f0d9ccc40786362ae4adSpectrum
GC-MStrans-Cinnamic acid, non-derivatized, GC-MS Spectrumsplash10-0ue9-0910000000-4a7bcdfadd383bf577dcSpectrum
GC-MStrans-Cinnamic acid, non-derivatized, GC-MS Spectrumsplash10-0fb9-6920000000-727a2eb761e6e52fb47dSpectrum
GC-MStrans-Cinnamic acid, non-derivatized, GC-MS Spectrumsplash10-117i-2920000000-f0d9ccc40786362ae4adSpectrum
Predicted GC-MStrans-Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ue9-2900000000-b105b3fcb63636d0d16fSpectrum
Predicted GC-MStrans-Cinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5dSpectrum
Predicted GC-MStrans-Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Cinnamic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-3107a2a1bec368528f822012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ufr-6900000000-b0299d34fa9bb16b82582012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-4a879de8ea4f3acb0ae22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-88ad8c9c837a057bb2a52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-18280fe18e43043d9e212012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fb9-9600000000-04d36ba7639bc85e20232012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a8417274c4493c5b58712012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9100000000-d3712417826a696679812012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-37c486fa03918355413c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f6t-0900000000-218a5babf0ab7c31c4982012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-88ad8c9c837a057bb2a52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-e3a4fcaa911f14d3790d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-9600000000-04d36ba7639bc85e20232017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a8417274c4493c5b58712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-d3712417826a696679812017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f6t-0900000000-218a5babf0ab7c31c4982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-f095c04fe81b2890cb1a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-1bb9599f57d5b1c1688b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-37c486fa03918355413c2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-f5b771d960092fa83d2c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-0900000000-58b4769b89ab3883fb052016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6900000000-9f4710d90f0cafac6d7b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-d015607beb51363244142016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-ff32add65ca52cbaae832016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-3900000000-f2450299b70c3ec0faec2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference