Identification

PhytoHub ID
PHUB000590
Name
Coumaric acid (p-)
Systematic Name
4'-hydroxycinnamic acid
Synonyms
  • (4-hydroxyphenyl)acrylic acid
  • 4-coumaric acid
  • 4-Hydroxycinnamic acid
  • p-coumaric acid
  • trans-4-hydroxycinnamic acid
CAS Number
501-98-4
Average Mass
164.16
Monoisotopic Mass
164.047344118
Chemical Formula
C9H8O3
IUPAC Name
(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
InChI Key
NGSWKAQJJWESNS-ZZXKWVIFSA-N
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+
SMILES
OC(=O)\C=C\C1=CC=C(O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
1.02e+00 g/l
LogS (ALOGPS)
-2.21
LogP (ALOGPS)
1.74
Hydrogen Acceptors
3
Hydrogen Donors
2
Rotatable Bond Count
2
Polar Surface Area
57.53
Refractivity
45.040800000000004
Polarizability
16.431404823804833
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.954717586543568
pKa (strongest acidic)
3.810198948389013
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Phenolic acids
Sub-class
Hydroxycinnamic acids

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Phenolic acid metabolites
Metabolite Sub-class
Cinnamic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
NaringeninPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Cranberry (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Tomato (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Blueberry (Poly)phenolsPolyphenolsNot specifiedNot AvailableShow Food Phytochemical
Propolis (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Grape (Poly)phenolsPolyphenolsNot specifiedNot specifiedShow Food Phytochemical
Coumaric acid (p-)PolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Cinnamic acids and derivatives
Super-class
Phenylpropanoids and polyketides
Sub-class
Hydroxycinnamic acids and derivatives
Direct Parent Name
Hydroxycinnamic acids
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acids", "Coumaric acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Styrenes"]
External Descriptor Annotations
["4-coumaric acid", "Paracoumaryl alcohol derivatives"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid", "Coumaric acid", "Coumaric acid or derivatives", "Hydrocarbon derivative", "Hydroxycinnamic acid", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Styrene"]

Spectra from Online Resources

Record IDSourceDescriptionView
JP007236MassBankEI-B Spectrum - -, [M]+*View Spectra
JP011903MassBankEI-B Spectrum - -, [M]+*View Spectra
KO000406MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO000407MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO000408MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO000409MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO000410MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
OUF00416MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PR100261MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100685MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100894MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100895MassBankLC-ESI-QTOF Spectrum - 30 V, unspecifiedView Spectra

Spectra from Phytohub

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919c2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-066v-3791000000-a5712bbe8401ef499b5a2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-3bb023f80c1f54a16adc2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-5900000000-a364c62c9122c0fbe6de2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066v-3791000000-a5712bbe8401ef499b5a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1891000000-d8804981d3918cac534d2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-7075c3e10f9df528109e2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-6390000000-3110f0f6eb462a38bb642017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-8900000000-3bb023f80c1f54a16adc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-b58aab08954c973df04e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-3ddb41572ba36a950e372012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-ccac7f071084bc6600952012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-3900000000-5dc8af06da0120779cff2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9500000000-9187edc4498ab4345e5a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-3900000000-1118928776a5a6e213db2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3d831c6acd9d3188de2f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-fbb6439b7d012045f3a82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0900000000-c5faa58d353ca1466c3c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0900000000-c45397049a7ba500b3322017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-b58aab08954c973df04e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-3ddb41572ba36a950e372017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-ccac7f071084bc6600952017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5dc8af06da0120779cff2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9500000000-9187edc4498ab4345e5a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3d831c6acd9d3188de2f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-fbb6439b7d012045f3a82017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-43c3377fad5f7488bea02016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-2264676cffcfb3110cb82016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdr-9600000000-9d441c7fc0720390be542016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-2ce3562ddd5762384d092016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-f6c69044556dd2ca21342016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-f7e5cd9359ebf2ee51a62016-09-12View Spectrum

Food Sources

NameGroup
American cranberryFruit, Berries PublicationsShow
AppleFruit, Pomes PublicationsShow
Apple ciderBeverages, Alcoholic PublicationsShow
Apple juiceBeverages, Non-alcoholic PublicationsShow
BeerBeverages, Alcoholic PublicationsShow
BlackberryFruit, Berries PublicationsShow
CoffeeCoffee and coffee products PublicationsShow
European cranberryFruit, Berries PublicationsShow
Olive, blackFruit, Drupes PublicationsShow
Olive, greenFruit, Drupes PublicationsShow
Orange juiceBeverages, Non-alcoholic PublicationsShow
PeanutNuts PublicationsShow
StrawberryFruit, Berries PublicationsShow
TomatoVegetables, Fruit vegetables PublicationsShow
Wheat breadCereals and cereal products PublicationsShow

Food Sources of its Food Phytochemical(s)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Coumaric acid (p-) p-Hydroxybenzoic acidhumanurineNot AvailableNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Publications
Coumaric acid (p-) Benzoic acidhumanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC7H6O2122.036779433
Coumaric acid (p-) Coumaric acid (p-)humanurineunchangedNot AvailableNot Available<1%C9H8O3164.047344118 Detailed Intervention Studies Publications
Coumaric acid (p-) Phloretic acidhumanurinehost metabolismNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Coumaric acid (p-) 3-Phenylpropionic acidhumanNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O2150.068079562 Publications
Coumaric acid (p-) Hippuric acidhumanplasma, urinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC9H9NO3179.058243154 Publications
Coumaric acid (p-) Coumaric acid-4'-O-glucuronideratplasmaNot AvailableNot AvailableNot AvailableNot AvailableC15H16O9340.079432095 Publications
Coumaric acid (p-) Coumaric acid-4'-sulfatehuman ratplasmahost metabolismNot Available0.5-2┬Ámol/LNot AvailableC9H8O6S244.004159152 Detailed Intervention Studies Publications
Coumaric acid (p-) Coumaric acid sulfoglucuronide (p-)ratplasmaNot AvailableNot AvailableNot AvailableNot AvailableC15H16O12S420.3492191 Publications
Naringenin Coumaric acid (p-)raturineNot AvailableNot AvailableNot AvailableNot AvailableC9H8O3164.047344118 Publications
Orange flavanones Coumaric acid (p-)humanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H8O3164.047344118 Detailed Intervention Studies Publications
Cranberry (Poly)phenols Coumaric acid (p-)humanplasma, urinegut microbiota metabolite5h-8h200-500 nmol/L<1%C9H8O3164.047344118 Detailed Intervention Studies Publications
Tomato (Poly)phenols Coumaric acid (p-)humanurinegut microbiota metaboliteNot AvailableNot Available5-10%C9H8O3164.047344118 Detailed Intervention Studies Publications
Blueberry (Poly)phenols Coumaric acid (p-)humanplasmahost metabolism1h-3h<20 nmol/LNot AvailableC9H8O3164.047344118 Detailed Intervention Studies Publications
Propolis (Poly)phenols Coumaric acid (p-)humanplasmahost metabolism1h-3h20-50 nmol/LNot AvailableC9H8O3164.047344118 Detailed Intervention Studies Publications
Coffee Chlorogenic acids Coumaric acid (p-)humanplasmahost metabolism1h-3h<20 nmol/LNot AvailableC9H8O3164.047344118 Detailed Intervention Studies Publications
Grape (Poly)phenols Coumaric acid (p-)humanplasma, urinehost metabolism<1h50-200 nmol/L<1%C9H8O3164.047344118 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Coffee Chlorogenic acids Coumaric acid (p-)MicrobiotaEffect, clusters Publications
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