Showing Compound trans-p-Coumaric acid (FDB002594)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:26 UTC

Update date

2025-11-18 22:38:34 UTC

Primary ID

FDB002594

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

trans-p-Coumaric acid

Description

Widespread in plants, e.g. peel of black cherry (Prunus serotina), lentil seeds and from red clover (Trifolium pratense). Found by Bate-Smith in 48% of investigated dicotyledonous and 55% of monocotyledonous subspecies Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. trans-p-Coumaric acid is found in many foods, some of which are common buckwheat, radish, sweet orange, and avocado.

CAS Number

501-98-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(2E)-3-(4-Hydroxyphenyl)acrylic acid	ChEBI
(e)-3-(4-Hydroxyphenyl)-2-propenoic acid	ChEBI
(e)-p-Coumaric acid	ChEBI
(e)-p-Hydroxycinnamic acid	ChEBI
4'-HYDROXYCINNAMIC ACID	ChEBI
Naringeninic acid	ChEBI
p-Coumaric acid	ChEBI
trans-p-Coumaric acid	ChEBI
trans-p-Coumarinic acid	ChEBI
trans-p-Hydroxycinnamate	ChEBI
trans-p-Hydroxycinnamic acid	ChEBI
trans-4-Hydroxycinnamate	Kegg
4-Hydroxycinnamate	Kegg
(2E)-3-(4-Hydroxyphenyl)acrylate	Generator
(e)-3-(4-Hydroxyphenyl)-2-propenoate	Generator
(e)-p-Coumarate	Generator
(e)-p-Hydroxycinnamate	Generator
4'-HYDROXYCINNAMate	Generator
Naringeninate	Generator
p-Coumarate	Generator
trans-p-Coumarate	Generator
trans-p-Coumarinate	Generator
4-Coumaric acid, (e)-isomer	MeSH
4-Coumaric acid, (Z)-isomer	MeSH
4-Coumaric acid, disodium salt	MeSH
p-Coumaryl alcohol	MeSH
p-Hydroxycinnamic acid	MeSH
Para-coumaric acid	MeSH
trans-3-(4'-Hydroxyphenyl)-2-propenoic acid	MeSH
trans-HPPA	MeSH
3-(4-Hydroxyphenyl)-2-propenoate	HMDB
3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
3-(4-Hydroxyphenyl)acrylate	HMDB
3-(4-Hydroxyphenyl)acrylic acid	HMDB
4-Coumarate	HMDB
4-Hydroxy cinnamate	HMDB
4-Hydroxy cinnamic acid	HMDB
4-Hydroxyphenylpropenoate	HMDB
4-Hydroxyphenylpropenoic acid	HMDB
b-[4-Hydroxyphenyl]acrylate	HMDB
b-[4-Hydroxyphenyl]acrylic acid	HMDB
beta-[4-Hydroxyphenyl]acrylate	HMDB
beta-[4-Hydroxyphenyl]acrylic acid	HMDB
cis-P-Coumarate	HMDB
Hydroxycinnamate	HMDB
Hydroxycinnamic acid	HMDB
P-Cumarate	HMDB
P-Cumaric acid	HMDB
P-Hydroxycinnamate	HMDB
P-Hydroxyphenylacrylate	HMDB
P-Hydroxyphenylacrylic acid	HMDB
Para coumarate	HMDB
Para coumaric acid	HMDB
Para-coumarate	HMDB
4-Hydroxycinnamic acid	ChEBI
trans-4-Coumarate	Generator, HMDB
(2E)-3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid	HMDB
(E)-3-(4-Hydroxyphenyl)acrylic acid	HMDB
(E)-4-Hydroxycinnamic acid	HMDB
4’-Hydroxycinnamic acid	HMDB
p-Cumaric acid	HMDB
p-Hydroxy-trans-cinnamic acid	HMDB
p-Hydroxyphenylacrylic acid	HMDB
p-trans-Coumaric acid	HMDB
trans-3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
trans-4-Coumaric acid	HMDB
β-[4-Hydroxyphenyl]acrylic acid	HMDB
(E)-p-Coumaric acid	biospider
(E)-p-Hydroxycinnamic acid	biospider
2-Propenoic acid, 3-(4-hydroxyphenyl)-, (E)-	biospider
Cinnamic acid, p-hydroxy-, (E)-	biospider
p-Coumaric acid, trans	biospider
trans-4-Hydroxycinnamic acid	biospider

Predicted Properties

Property	Value	Source
Water Solubility	1.02 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	16.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H8O3

IUPAC name

(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid

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 Key

NGSWKAQJJWESNS-ZZXKWVIFSA-N

Isomeric SMILES

OC(=O)\C=C\C1=CC=C(O)C=C1

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

4-coumaric acid (CHEBI:32374 )
Paracoumaryl alcohol derivatives (C00811 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 65.85%; H 4.91%; O 29.24%	DFC
Melting Point	Mp 210-213°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	1.79	SANGSTER (1994)
Experimental pKa	pKa2 9.45 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	286 (e 19000) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03xr-6900000000-348f5c7c030570e0612f	2015-03-01	View Spectrum
GC-MS	p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-014m-1981000000-e7648e85764a445a919c	Spectrum
GC-MS	p-Coumaric acid, 2 TMS, GC-MS Spectrum	splash10-066v-3791000000-a5712bbe8401ef499b5a	Spectrum
GC-MS	p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-03di-8900000000-3bb023f80c1f54a16adc	Spectrum
GC-MS	p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-03xr-5900000000-a364c62c9122c0fbe6de	Spectrum
GC-MS	p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-014m-1981000000-e7648e85764a445a919c	Spectrum
GC-MS	p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-066v-3791000000-a5712bbe8401ef499b5a	Spectrum
GC-MS	p-Coumaric acid, non-derivatized, GC-MS Spectrum	splash10-014m-1891000000-d8804981d3918cac534d	Spectrum
Predicted GC-MS	p-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014j-2900000000-7075c3e10f9df528109e	Spectrum
Predicted GC-MS	p-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xu-6390000000-3110f0f6eb462a38bb64	Spectrum
Predicted GC-MS	p-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-03di-8900000000-3bb023f80c1f54a16adc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-b58aab08954c973df04e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-3ddb41572ba36a950e37	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-0900000000-ccac7f071084bc660095	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-3900000000-5dc8af06da0120779cff	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9500000000-9187edc4498ab4345e5a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00kb-3900000000-1118928776a5a6e213db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-0900000000-3d831c6acd9d3188de2f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-fbb6439b7d012045f3a8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0002-0900000000-9e18d43a8d86f9b9e72b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0002-0900000000-c5faa58d353ca1466c3c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-014i-0900000000-c45397049a7ba500b332	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-0900000000-b58aab08954c973df04e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-3ddb41572ba36a950e37	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-ccac7f071084bc660095	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-3900000000-5dc8af06da0120779cff	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kf-9500000000-9187edc4498ab4345e5a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-3d831c6acd9d3188de2f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-fbb6439b7d012045f3a8	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-43c3377fad5f7488bea0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-2264676cffcfb3110cb8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gdr-9600000000-9d441c7fc0720390be54	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-2ce3562ddd5762384d09	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-f6c69044556dd2ca2134	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014m-3900000000-f7e5cd9359ebf2ee51a6	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

498

DrugBank ID

Not Available

HMDB ID

HMDB0002035

CRC / DFC (Dictionary of Food Compounds) ID

CMP73-U:CMP74-V

EAFUS ID

Not Available

Dr. Duke ID

TRANS-P-COUMARIC-ACID|COUMARIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00000580

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

501-98-4

GoodScent ID

rw1203781

SuperScent ID

Not Available

Wikipedia ID

Coumaric_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
balsamic	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.