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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2019-07-23 05:45:15 UTC
HMDB IDHMDB0002035
Secondary Accession Numbers
  • HMDB02035
Metabolite Identification
Common Name4-Hydroxycinnamic acid
Description4-Hydroxycinnamic acid, also known as trans-p-hydroxycinnamate or p-coumaric acid, 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. 4-Hydroxycinnamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxycinnamic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 4-Hydroxycinnamic acid is found, on average, in the highest concentration within a few different foods, such as pepper (c. frutescens), pineapples, and sunflowers and in a lower concentration in spinachs, kiwis, and sweet oranges. 4-Hydroxycinnamic acid has also been detected, but not quantified in, several different foods, such as wild rices, soursops, garden onions, hyssops, and avocado. This could make 4-hydroxycinnamic acid a potential biomarker for the consumption of these foods. The trans-isomer of 4-coumaric acid.
Structure
Data?1563860715
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
trans-4-HydroxycinnamateKegg
4-HydroxycinnamateKegg
(2E)-3-(4-Hydroxyphenyl)acrylateGenerator
(e)-3-(4-Hydroxyphenyl)-2-propenoateGenerator
(e)-p-CoumarateGenerator
(e)-p-HydroxycinnamateGenerator
4'-HYDROXYCINNAMateGenerator
NaringeninateGenerator
p-CoumarateGenerator
trans-p-CoumarateGenerator
trans-p-CoumarinateGenerator
trans-4-CoumarateHMDB
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)-isomerHMDB
4-Coumaric acid, disodium saltHMDB
4-Coumaric acid, (e)-isomerHMDB
p-Coumaryl alcoholHMDB
trans-3-(4'-Hydroxyphenyl)-2-propenoic acidHMDB
trans-HPPAHMDB
(2E)-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acidHMDB
(e)-3-(4-Hydroxyphenyl)acrylic acidHMDB
(e)-4-Hydroxycinnamic acidHMDB
4’-hydroxycinnamic acidHMDB
p-Hydroxy-trans-cinnamic acidHMDB
p-trans-Coumaric acidHMDB
trans-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
trans-4-Coumaric acidHMDB
Β-[4-hydroxyphenyl]acrylic acidHMDB
4-Hydroxycinnamic acidChEBI
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 Number501-98-4
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
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:

Role

Biological role:

Industrial application:

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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-066v-3791000000-a5712bbe8401ef499b5aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-3bb023f80c1f54a16adcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-5900000000-a364c62c9122c0fbe6deJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066v-3791000000-a5712bbe8401ef499b5aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1891000000-d8804981d3918cac534dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-7075c3e10f9df528109eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-6390000000-3110f0f6eb462a38bb64JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-8900000000-3bb023f80c1f54a16adcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-b58aab08954c973df04eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-3ddb41572ba36a950e37JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-ccac7f071084bc660095JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-3900000000-5dc8af06da0120779cffJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9500000000-9187edc4498ab4345e5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-3900000000-1118928776a5a6e213dbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3d831c6acd9d3188de2fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-fbb6439b7d012045f3a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0900000000-c5faa58d353ca1466c3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0900000000-c45397049a7ba500b332JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-b58aab08954c973df04eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-3ddb41572ba36a950e37JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-ccac7f071084bc660095JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5dc8af06da0120779cffJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9500000000-9187edc4498ab4345e5aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3d831c6acd9d3188de2fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-fbb6439b7d012045f3a8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-43c3377fad5f7488bea0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-2264676cffcfb3110cb8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdr-9600000000-9d441c7fc0720390be54JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-2ce3562ddd5762384d09JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-f6c69044556dd2ca2134JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-f7e5cd9359ebf2ee51a6JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03xr-6900000000-348f5c7c030570e0612fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified0.6 +/- 0.253 uMAdult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified7.980 +/- 0.244 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified8.467 +/- 1.218 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified9.0766 +/- 2.132 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified9.381 +/- 2.0712 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected and Quantified0.323 (0.0122-1.578) nmol/g wet fecesAdult (>18 years old)Both
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04066
Phenol Explorer Compound ID500
FoodDB IDFDB002593
KNApSAcK IDC00000580
Chemspider ID553148
KEGG Compound IDC00811
BioCyc IDCOUMARATE
BiGG ID36077
Wikipedia LinkP-Coumaric_acid
METLIN ID6450
PubChem Compound637542
PDB IDNot Available
ChEBI ID32374
Food Biomarker OntologyNot Available
VMH IDT4HCINNM
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 ]
  5. Vargas-Tah A, Gosset G: Production of Cinnamic and p-Hydroxycinnamic Acids in Engineered Microbes. Front Bioeng Biotechnol. 2015 Aug 20;3:116. doi: 10.3389/fbioe.2015.00116. eCollection 2015. [PubMed:26347861 ]

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:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
cis-beta-D-Glucosyl-2-hydroxycinnamate + Water → 4-Hydroxycinnamic acid + D-Glucosedetails
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 → ​p-Coumaric acid sulfatedetails