Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2020-02-24 19:10:33 UTC
Primary IDFDB002592
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-p-Coumaric acid
Descriptioncis-p-Coumaric acid, also known as cis-4-hydroxycinnamate or cis-p-coumarate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. cis-p-Coumaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). cis-p-Coumaric acid is found, on average, in the highest concentration within corianders. This could make cis-p-coumaric acid a potential biomarker for the consumption of these foods.
CAS Number4501-31-9
Structure
Thumb
Synonyms
SynonymSource
(2Z)-3-(4-Hydroxyphenyl)acrylic acidChEBI
(Z)-3-(4-Hydroxyphenyl)-2-propenoic acidChEBI
(Z)-p-Coumaric acidChEBI
(Z)-p-Hydroxycinnamic acidChEBI
cis-4-Hydroxycinnamic acidChEBI
cis-p-CoumarateChEBI
cis-p-Coumarinic acidChEBI
cis-p-Hydroxycinnamic acidChEBI
(2Z)-3-(4-Hydroxyphenyl)acrylateGenerator
(Z)-3-(4-Hydroxyphenyl)-2-propenoateGenerator
(Z)-p-CoumarateGenerator
(Z)-p-HydroxycinnamateGenerator
cis-4-HydroxycinnamateGenerator
cis-p-CoumarinateGenerator
cis-p-HydroxycinnamateGenerator
cis-4-CoumarateHMDB
(2Z)-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
(2Z)-3-(4-Hydroxyphenyl)prop-2-enoic acidHMDB
(Z)-3-(4-Hydroxyphenyl)acrylic acidHMDB
(Z)-4-Hydroxycinnamic acidHMDB
3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxyphenyl)acrylic acidHMDB
4-Coumaric acidHMDB
4-Hydroxycinnamic acidHMDB
beta-[4-Hydroxyphenyl]acrylic acidHMDB
cis-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
cis-4-Coumaric acidHMDB
p-Coumaric acidHMDB
p-Cumaric acidHMDB
p-Hydroxy-cis-cinnamic acidHMDB
p-Hydroxycinnamic acidHMDB
p-Hydroxyphenylacrylic acidHMDB
p-cis-Coumaric acidHMDB
Β-[4-hydroxyphenyl]acrylic acidHMDB
cis-p-Coumaric acidChEBI
(Z)-P-CoumarateGenerator
(Z)-P-Coumaric acidChEBI
(Z)-P-HydroxycinnamateGenerator
(Z)-P-Hydroxycinnamic acidChEBI
cis-p-coumaratebiospider
cis-P-CoumarinateGenerator
cis-P-Coumarinic acidChEBI
cis-P-HydroxycinnamateGenerator
cis-P-Hydroxycinnamic acidChEBI
Predicted Properties
PropertyValueSource
Water Solubility1.02 g/LALOGPS
logP1.74ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O3
IUPAC name(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-
InChI KeyNGSWKAQJJWESNS-UTCJRWHESA-N
Isomeric SMILESOC(=O)\C=C/C1=CC=C(O)C=C1
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
Classification
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.85%; H 4.91%; O 29.24%DFC
Melting PointMp 134-134.5 dec. (subl. from 124°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.79SANGSTER (1994)
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
GC-MScis-p-Coumaric acid, 2 TMS, GC-MS Spectrumsplash10-014m-2691000000-eaa9fb96842966079178Spectrum
GC-MScis-p-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-014m-2691000000-eaa9fb96842966079178Spectrum
Predicted GC-MScis-p-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-1900000000-06b9af47d2378036e0f4Spectrum
Predicted GC-MScis-p-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-6390000000-3110f0f6eb462a38bb64Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-43c3377fad5f7488bea0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-2264676cffcfb3110cb8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdr-9600000000-9d441c7fc0720390be54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-2ce3562ddd5762384d09Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-f6c69044556dd2ca2134Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-f7e5cd9359ebf2ee51a6Spectrum
NMRNot Available
ChemSpider ID1266072
ChEMBL IDCHEMBL2336752
KEGG Compound IDC06738
Pubchem Compound ID1549106
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID500
DrugBank IDNot Available
HMDB IDHMDB30677
CRC / DFC (Dictionary of Food Compounds) IDCMP73-U:CMP68-W
EAFUS IDNot Available
Dr. Duke IDCIS-P-COUMARIC-ACID
BIGG IDNot Available
KNApSAcK IDC00038791
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCoumaric_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).