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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:17 UTC
HMDB IDHMDB0000567
Secondary Accession Numbers
  • HMDB00567
Metabolite Identification
Common NameCinnamic 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. It is obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Cinnamic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, cinnamic acid has been detected, but not quantified in, chinese cinnamons. This could make cinnamic acid a potential biomarker for the consumption of these foods. The original synthesis of cinnamic acid involves the Perkin reaction, which entails the base-catalysed condensation of acetic anhydride and benzaldehyde. Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships. Cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids.
Structure
Data?1563860657
Synonyms
ValueSource
(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
(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
Cinnamic acidHMDB
Isocinnamic acidHMDB
cis-Cinnamic acidHMDB
β-Phenylacrylic acidHMDB
Chemical FormulaC9H8O2
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
IUPAC Name(2Z)-3-phenylprop-2-enoic acid
Traditional Namecis-cinnamic acid
CAS Registry Number102-94-3
SMILES
OC(=O)\C=C/C1=CC=CC=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point132 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.57 mg/mL at 25 °CNot Available
LogP2.13HANSCH,C ET AL. (1995)
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1900000000-f00ddafc38ffb949fd1fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5dJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-066s-4900000000-f4bfd33daf0938375a0dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-0900000000-d93fb5a9c15682c1e6eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-004i-9000000000-9be1ef1ea4500691cb22JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-1357b63887db6df1be7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0900000000-b8c6ecaf3fa85d1487a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-7900000000-0805b8dbbbd2777f28c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-6e7b31576f8ffd356252JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f92-0900000000-c5fb484b178fce86b596JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-1900000000-36b618a3b50dc51ff302JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.168 +/- 0.044 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.194 +/- 0.05 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.279 +/- 0.051 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.261 +/- 0.052 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.134 +/- 0.039 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.142 +/- 0.035 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.342 +/- 0.242 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.111 +/- 0.03 uMAdult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.77 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified1.6 (0.9-2.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.069 +/- 0.022 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012698
KNApSAcK IDC00029961
Chemspider ID10286933
KEGG Compound IDC10438
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinnamic acid
METLIN ID310
PubChem Compound5372954
PDB IDNot Available
ChEBI ID35699
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceAn, Hong; He, Xifeng; Fu, Jing. Synthesis of cinnamic acid. Huagong Shikan (2005), 19(7), 32-33, 41.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kukongviriyapan V, Phromsopha N, Tassaneeyakul W, Kukongviriyapan U, Sripa B, Hahnvajanawong V, Bhudhisawasdi V: Inhibitory effects of polyphenolic compounds on human arylamine N-acetyltransferase 1 and 2. Xenobiotica. 2006 Jan;36(1):15-28. [PubMed:16507510 ]