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Record Information
Version3.6
Creation Date2006-05-22 14:17:33 UTC
Update Date2016-06-10 21:22:13 UTC
HMDB IDHMDB02035
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Hydroxycinnamic acid
Description4-Hydroxycinnamic acid is a yellowish green crystalline powder. Cinnamic acid and its derivatives are used as important components in flavours, perfumes, synthetic indigo and pharmaceuticals.
Structure
Thumb
Synonyms
ValueSource
(2E)-3-(4-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(4-Hydroxyphenyl)-2-propenoic acidChEBI
(e)-P-Coumaric acidChEBI
(e)-P-Hydroxycinnamic acidChEBI
4'-HYDROXYCINNAMIC ACIDChEBI
4-Hydroxycinnamic acidChEBI
Naringeninic acidChEBI
P-Coumaric acidChEBI
trans-4-Hydroxycinnamic acidChEBI
trans-P-Coumaric acidChEBI
trans-P-Coumarinic acidChEBI
trans-P-HydroxycinnamateChEBI
trans-P-Hydroxycinnamic acidChEBI
(2E)-3-(4-Hydroxyphenyl)acrylateGenerator
(e)-3-(4-Hydroxyphenyl)prop-2-enoateGenerator
(e)-3-(4-Hydroxyphenyl)-2-propenoateGenerator
(e)-P-CoumarateGenerator
(e)-P-HydroxycinnamateGenerator
4'-HYDROXYCINNAMateGenerator
4-HydroxycinnamateGenerator
NaringeninateGenerator
P-CoumarateGenerator
trans-4-HydroxycinnamateGenerator
trans-P-CoumarateGenerator
trans-P-CoumarinateGenerator
3-(4-Hydroxyphenyl)-2-propenoateHMDB
3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxyphenyl)acrylateHMDB
3-(4-Hydroxyphenyl)acrylic acidHMDB
4-CoumarateHMDB
4-Coumaric acidHMDB
4-Hydroxy cinnamateHMDB
4-Hydroxy cinnamic acidHMDB
4-HydroxyphenylpropenoateHMDB
4-Hydroxyphenylpropenoic acidHMDB
b-[4-Hydroxyphenyl]acrylateHMDB
b-[4-Hydroxyphenyl]acrylic acidHMDB
beta-[4-Hydroxyphenyl]acrylateHMDB
beta-[4-Hydroxyphenyl]acrylic acidHMDB
cis-P-CoumarateHMDB
HydroxycinnamateHMDB
Hydroxycinnamic acidHMDB
P-CumarateHMDB
P-Cumaric acidHMDB
P-HydroxycinnamateHMDB
P-Hydroxycinnamic acidHMDB
P-HydroxyphenylacrylateHMDB
P-Hydroxyphenylacrylic acidHMDB
Para coumarateHMDB
Para coumaric acidHMDB
Para-coumarateHMDB
Para-coumaric acidHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Namecoumaric acid
CAS Registry Number7400-08-0
SMILES
OC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
InChI KeyInChIKey=NGSWKAQJJWESNS-ZZXKWVIFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These 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
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Coumaric acid
  • Cinnamic acid
  • Phenylpropene
  • Styrene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point211.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.79SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility1.02 mg/mLALOGPS
logP1.74ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m3·mol-1ChemAxon
Polarizability16.43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014m-1981000000-e7648e85764a445a919cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-066v-3791000000-a5712bbe8401ef499b5aView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-8900000000-3bb023f80c1f54a16adcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-b58aab08954c973df04eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-3ddb41572ba36a950e37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-ccac7f071084bc660095View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-3900000000-5dc8af06da0120779cffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9500000000-9187edc4498ab4345e5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-3900000000-1118928776a5a6e213dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3d831c6acd9d3188de2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-fbb6439b7d012045f3a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-03xr-6900000000-348f5c7c030570e0612fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.116 +/- 0.045 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.071 +/- 0.024 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.174 +/- 0.045 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.148 +/- 0.033 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.057 +/- 0.014 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.052 +/- 0.01 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.049 +/- 0.004 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.94 +/- 0.897 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected and Quantified7.980 +/- 0.244 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified8.467 +/- 1.218 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified9.0766 +/- 2.132 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified9.381 +/- 2.0712 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.31-0.57 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454
  • Not Applicable
details
UrineDetected and Quantified0.29-0.45 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID500
Phenol Explorer Metabolite ID454
FoodDB IDFDB002593
KNApSAcK IDC00000152
Chemspider ID553148
KEGG Compound IDC00811
BioCyc IDCOUMARATE
BiGG ID36077
Wikipedia Linkhydroxycinnamic acid
NuGOwiki LinkHMDB02035
Metagene LinkHMDB02035
METLIN ID6450
PubChem Compound637542
PDB IDHC4
ChEBI ID32374
References
Synthesis ReferenceBen-Bassat, Arie; Sariaslani, Fateme Sima; Huang, Lisa L.; Patnaik, Ranjan; Lowe, David J. Fermentative preparation of para-hydroxycinnamic acid and cinnamic acid at alkaline ph. U.S. Pat. Appl. Publ. (2005), 23 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. [10706426 ]
  2. Phan TT, Sun L, Bay BH, Chan SY, Lee ST: Dietary compounds inhibit proliferation and contraction of keloid and hypertrophic scar-derived fibroblasts in vitro: therapeutic implication for excessive scarring. J Trauma. 2003 Jun;54(6):1212-24. [12813346 ]
  3. Zhao Z, Egashira Y, Sanada H: Phenolic antioxidants richly contained in corn bran are slightly bioavailable in rats. J Agric Food Chem. 2005 Jun 15;53(12):5030-5. [15941352 ]
  4. Brivet M, Garcia-Cazorla A, Lyonnet S, Dumez Y, Nassogne MC, Slama A, Boutron A, Touati G, Legrand A, Saudubray JM: Impaired mitochondrial pyruvate importation in a patient and a fetus at risk. Mol Genet Metab. 2003 Mar;78(3):186-92. [12649063 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69