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Showing Compound cis-Cinnamic acid (FDB012698)

Record Information
Version1.0
Creation date2010-04-08 22:10:19 UTC
Update date2019-11-26 03:07:24 UTC
Primary IDFDB012698
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-Cinnamic acid
DescriptionCinnamic acid, also known as (Z)-cinnamate or 3-phenyl-acrylate, 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. Cinnamic acid exists in all living organisms, ranging from bacteria to humans. Cinnamic acid has been detected, but not quantified in, beer and chinese cinnamons (Cinnamomum aromaticum). This could make cinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cinnamic acid.
CAS Number102-94-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2Z)-3-Phenyl-2-propenoic acidChEBI
(2Z)-3-Phenylacrylic acidChEBI
(Z)-3-Phenyl-2-propenoic acidChEBI
(Z)-Cinnamic acidChEBI
cis-beta-CarboxystyreneChEBI
cis-ZimtsaeureChEBI
(2Z)-3-Phenyl-2-propenoateGenerator
(2Z)-3-PhenylacrylateGenerator
(Z)-3-Phenyl-2-propenoateGenerator
(Z)-CinnamateGenerator
cis-b-CarboxystyreneGenerator
cis-Β-carboxystyreneGenerator
CinnamateGenerator
Cinnamic acid, 1-(13)C-labeled CPDHMDB
Cinnamic acid, 13C-labeled CPDHMDB
trans-Cinnamic acidHMDB
(e)-Cinnamic acid, 2-(14)C-labeled CPDHMDB
Cinnamic acid, (Z)-isomerHMDB
Cinnamic acid, (trans)-(e)-isomerHMDB
Cinnamic acid, 14C-labeled CPDHMDB
Cinnamic acid, 3H-labeled CPD (Z)-isomerHMDB
Cinnamic acid, sodium saltHMDB
Cinnamic acid, sodium salt(Z)-isomerHMDB
Sodium cinnamateHMDB
e-Z Cinnamic acidHMDB
Cinnamic acid, 2-(13)C-labeled CPDHMDB
Cinnamic acid, 2-(14)C-labeled CPDHMDB
Cinnamic acid, 3-(14)C-labeled CPDHMDB
Cinnamic acid, radical ion(1-)HMDB
e-Cinnamic acidHMDB
Cinnamic acid, 1-14C-labeled CPDHMDB
Cinnamic acid, 14C-labeled CPD (e)-isomerHMDB
Cinnamic acid, 3H-labeled CPD (e)-isomerHMDB
Cinnamic acid, ion(1-)HMDB
Cinnamic acid, ion(1-)-(e)-isomerHMDB
Cinnamic acid, nickel (+2) saltHMDB
Cinnamic acid, potassium saltHMDB
Cinnamic acid, sodium salt(e)-isomerHMDB
Cinnamic acid, zinc salt(e)-isomerHMDB
Tritium labeled (e)-cinnamic acidHMDB
Tritium labeled (Z)-cinnamic acidHMDB
(e)-3-Phenyl-2-propenoateHMDB
(e)-3-Phenyl-2-propenoic acidHMDB
3-Phenyl-2-propenoateHMDB
3-Phenyl-2-propenoic acidHMDB
3-Phenyl-acrylateHMDB
3-Phenyl-acrylic acidHMDB
3-PhenylacrylateHMDB
3-Phenylacrylic acidHMDB
3-PhenylpropenoateHMDB
3-Phenylpropenoic acidHMDB
BenzenepropenoateHMDB
Benzenepropenoic acidHMDB
Benzylideneacetic acidHMDB
beta-Phenylacrylic acidHMDB
Cinnamylic acidHMDB
PhenylacrylateHMDB
Phenylacrylic acidHMDB
cis-CinnamateHMDB
(Z)-3-Phenylacrylic acidHMDB
Allocinnamic acidHMDB
Isocinnamic acidHMDB
cis-Cinnamic acidHMDB
Β-phenylacrylic acidHMDB
Cinnamic acidHMDB
(2Z)-3-Phenylprop-2-enoic acidbiospider
2-Propenoic acid, 3-phenyl-, (Z)-biospider
Cinnamic acid, (Z)-biospider
cis-β-Carboxystyrenebiospider
Z-Cinnamic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O2
IUPAC name(2Z)-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-SREVYHEPSA-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 stateNot Available
Physical DescriptionNot Available
Mass CompositionC 72.96%; H 5.44%; O 21.60%DFC
Melting PointMp 68° (trimorph.)DFC
Boiling PointBp 95° (high vac.)DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 3.85 (25°)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
Predicted GC-MSCinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1900000000-f00ddafc38ffb949fd1fSpectrum
Predicted GC-MSCinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5dSpectrum
Predicted GC-MSCinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCinnamic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-066s-4900000000-f4bfd33daf0938375a0d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-0900000000-d93fb5a9c15682c1e6ee2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-004i-9000000000-9be1ef1ea4500691cb222012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b4400af8b5aad0d8d3232021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9700000000-7d7dbe711d881767830e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-20d69cc859de39f180042021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-1357b63887db6df1be7a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0900000000-b8c6ecaf3fa85d1487a62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-7900000000-0805b8dbbbd2777f28c42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-6e7b31576f8ffd3562522017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f92-0900000000-c5fb484b178fce86b5962017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-1900000000-36b618a3b50dc51ff3022017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-5a19a7768eb87376d23c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-138b8c24fd394024a31a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-dd9a9ae0caad4bca05c82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-530f30f323b6e6a533942021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-648b395c048d84ce7d9a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9600000000-cb54ab97d7414eccc8742021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, 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 ID5372954
Pubchem Substance IDNot Available
ChEBI ID35699
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHCV54-E:HJX16-B
EAFUS IDNot Available
Dr. Duke IDCIS-CINNAMIC-ACID
BIGG IDNot Available
KNApSAcK IDC00034743
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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
FlavoursNot Available
Files
MSDSNot Available
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).