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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:29:32 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. Cinnamic acid can be 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 plants to humans. Outside of the human body, cinnamic acid has been detected, but not quantified in, chinese cinnamons. In plants, 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?1582752140
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
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
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point132 - 135 °CNot Available
Boiling Point265.00 to 266.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.57 mg/mL at 25 °CNot Available
LogP2.13HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker145.3130932474
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.7231661259
DarkChem[M-H]-126.86731661259
AllCCS[M+H]+130.30532859911
AllCCS[M-H]-128.56532859911
DeepCCS[M+H]+129.70930932474
DeepCCS[M-H]-126.85630932474
DeepCCS[M-2H]-163.00330932474
DeepCCS[M+Na]+138.27430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cinnamic acidOC(=O)\C=C/C1=CC=CC=C12773.6Standard polar33892256
Cinnamic acidOC(=O)\C=C/C1=CC=CC=C11370.5Standard non polar33892256
Cinnamic acidOC(=O)\C=C/C1=CC=CC=C11442.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cinnamic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C1=CC=CC=C11551.3Semi standard non polar33892256
Cinnamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C1=CC=CC=C11791.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1900000000-f00ddafc38ffb949fd1f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnamic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-066s-4900000000-f4bfd33daf0938375a0d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0udi-0900000000-d93fb5a9c15682c1e6ee2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-004i-9000000000-9be1ef1ea4500691cb222012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamic acid 40V, Negative-QTOFsplash10-004i-9000000000-b4400af8b5aad0d8d3232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamic acid 20V, Negative-QTOFsplash10-0fb9-9700000000-7d7dbe711d881767830e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinnamic acid 10V, Negative-QTOFsplash10-0udi-0900000000-20d69cc859de39f180042021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 10V, Positive-QTOFsplash10-001i-0900000000-1357b63887db6df1be7a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 20V, Positive-QTOFsplash10-0f89-0900000000-b8c6ecaf3fa85d1487a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 40V, Positive-QTOFsplash10-0udi-7900000000-0805b8dbbbd2777f28c42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 10V, Negative-QTOFsplash10-0002-0900000000-6e7b31576f8ffd3562522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 20V, Negative-QTOFsplash10-0f92-0900000000-c5fb484b178fce86b5962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 40V, Negative-QTOFsplash10-0fb9-1900000000-36b618a3b50dc51ff3022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 10V, Negative-QTOFsplash10-0udi-0900000000-5a19a7768eb87376d23c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 20V, Negative-QTOFsplash10-0udi-0900000000-138b8c24fd394024a31a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 40V, Negative-QTOFsplash10-004i-9200000000-dd9a9ae0caad4bca05c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 10V, Positive-QTOFsplash10-001i-0900000000-530f30f323b6e6a533942021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 20V, Positive-QTOFsplash10-0udi-0900000000-648b395c048d84ce7d9a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamic acid 40V, Positive-QTOFsplash10-0fb9-9600000000-cb54ab97d7414eccc8742021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB012698
KNApSAcK IDC00034743
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
MarkerDB IDNot Available
Good Scents IDrw1123131
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 ]