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Record Information
Version4.0
Creation Date2006-05-22 14:17:33 UTC
Update Date2017-09-27 08:24:11 UTC
HMDB IDHMDB0002035
Secondary Accession Numbers
  • HMDB02035
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
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
4-HydroxycinnamateGenerator
(e)-3-(4-Hydroxyphenyl)-2-propenoateGenerator
(e)-P-CoumarateGenerator
(e)-P-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
4-Coumaric acid, (Z)-isomerMeSH
4-Coumaric acid, disodium saltMeSH
4-Coumaric acid, (e)-isomerMeSH
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 KeyNGSWKAQJJWESNS-ZZXKWVIFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCinnamic 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

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

    Cell:

Source:

Role

Industrial application:

  Pharmaceutical industry:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.43 ųChemAxon
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) (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-066v-3791000000-a5712bbe8401ef499b5aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-3bb023f80c1f54a16adcView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-5900000000-a364c62c9122c0fbe6deView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066v-3791000000-a5712bbe8401ef499b5aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1891000000-d8804981d3918cac534dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-7075c3e10f9df528109eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-6390000000-3110f0f6eb462a38bb64View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0900000000-c5faa58d353ca1466c3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0900000000-c45397049a7ba500b332View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-b58aab08954c973df04eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-3ddb41572ba36a950e37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-ccac7f071084bc660095View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5dc8af06da0120779cffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9500000000-9187edc4498ab4345e5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3d831c6acd9d3188de2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-fbb6439b7d012045f3a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-43c3377fad5f7488bea0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-2264676cffcfb3110cb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdr-9600000000-9d441c7fc0720390be54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-2ce3562ddd5762384d09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-f6c69044556dd2ca2134View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-f7e5cd9359ebf2ee51a6View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03xr-6900000000-348f5c7c030570e0612fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Fibroblasts
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
FecesDetected but not Quantified Infant (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 Quantified Not SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.31-0.57 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 454 details
UrineDetected and Quantified0.29-0.45 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.142 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0160-2.940 umol/mmol creatinineAdult (>18 years old)Both
Normal
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
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Hydroxycinnamic acid → 6-{4-[(1E)-2-carboxyeth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
4-Hydroxycinnamic acid → 3,4,5-trihydroxy-6-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-Hydroxycinnamic acid → (2E)-3-[4-(sulfooxy)phenyl]prop-2-enoic aciddetails