trans-4-coumaric acid (CHEBI:32374)

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CHEBI:32374 - trans-4-coumaric acid

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ChEBI Name	trans-4-coumaric acid

ChEBI ID	CHEBI:32374

ChEBI ASCII Name	trans-4-coumaric acid

Definition	The trans-isomer of 4-coumaric acid.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43108, CHEBI:1812, CHEBI:15796, CHEBI:27061

Supplier Information	ChemicalBook:CB6164395, ChemicalBook:CB9164396, ChemicalBook:CB1940606, eMolecules:494417, ZINC000000039811

Download	Molfile XML SDF

more structures >>

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Wikipedia	License
p-Coumaric acid is an organic compound with the formula HOC6H4CH=CHCO2H. It is one of the three isomers of hydroxycinnamic acid. It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether.
Read full article at Wikipedia

Formula

C9H8O3

Net Charge

Average Mass

164.15802

Monoisotopic Mass

164.04734

InChI

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

InChIKey

NGSWKAQJJWESNS-ZZXKWVIFSA-N

SMILES

OC(=O)\C=C\c1ccc(O)cc1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	food component A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via 4-coumaric acid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	trans-4-coumaric acid (CHEBI:32374) has role food component (CHEBI:78295) trans-4-coumaric acid (CHEBI:32374) has role mouse metabolite (CHEBI:75771) trans-4-coumaric acid (CHEBI:32374) has role plant metabolite (CHEBI:76924) trans-4-coumaric acid (CHEBI:32374) is a 4-coumaric acid (CHEBI:36090) trans-4-coumaric acid (CHEBI:32374) is conjugate acid of trans-4-coumarate (CHEBI:12876)

Incoming	(2R,3S)-trans-coutaric acid (CHEBI:76095) has functional parent trans-4-coumaric acid (CHEBI:32374) (E)-p-coumaroylagmatine (CHEBI:86080) has functional parent trans-4-coumaric acid (CHEBI:32374) 1-O-(4-coumaroyl)-β-D-glucose (CHEBI:71498) has functional parent trans-4-coumaric acid (CHEBI:32374) 3-β-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid (CHEBI:65663) has functional parent trans-4-coumaric acid (CHEBI:32374) 3-O-(trans-4-coumaroyl)-β-D-glucopyranose (CHEBI:76094) has functional parent trans-4-coumaric acid (CHEBI:32374) 3-O-trans-p-coumaroyl actinidic acid (CHEBI:65661) has functional parent trans-4-coumaric acid (CHEBI:32374) 4-acetoxycinnamic acid (CHEBI:86580) has functional parent trans-4-coumaric acid (CHEBI:32374) 6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) has functional parent trans-4-coumaric acid (CHEBI:32374) 6-O-(trans-4-coumaroyl)-α-D-glucopyranose (CHEBI:76092) has functional parent trans-4-coumaric acid (CHEBI:32374) 6-O-(trans-4-coumaroyl)-β-D-glucopyranose (CHEBI:76089) has functional parent trans-4-coumaric acid (CHEBI:32374) N¹,N⁵,N¹⁰-(E)-tri-p-coumaroylspermidine (CHEBI:232336) has functional parent trans-4-coumaric acid (CHEBI:32374) N¹,N⁸-bis(coumaroyl)spermidine (CHEBI:85530) has functional parent trans-4-coumaric acid (CHEBI:32374) trans-4-coumaroyl-CoA (CHEBI:85531) has functional parent trans-4-coumaric acid (CHEBI:32374) asprellic acid A (CHEBI:65455) has functional parent trans-4-coumaric acid (CHEBI:32374) asprellic acid C (CHEBI:65456) has functional parent trans-4-coumaric acid (CHEBI:32374) brevipolide A (CHEBI:65522) has functional parent trans-4-coumaric acid (CHEBI:32374) coniferyl p-coumarate (CHEBI:86599) has functional parent trans-4-coumaric acid (CHEBI:32374) cyanidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:29560) has functional parent trans-4-coumaric acid (CHEBI:32374) cyanidin 3-O-{6-O-[6-O-(4-coumaroyl)-β-D-glucosyl]-2-O-β-D-xylosyl-β-D-galactoside} (CHEBI:71499) has functional parent trans-4-coumaric acid (CHEBI:32374) delphinidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:75677) has functional parent trans-4-coumaric acid (CHEBI:32374) isorhamnetin 3-O-α-L-[6''''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside] (CHEBI:66097) has functional parent trans-4-coumaric acid (CHEBI:32374) kaempferol 3-O-α-L-[6'''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside] (CHEBI:66131) has functional parent trans-4-coumaric acid (CHEBI:32374) kaempferol 3-O-α-L-[6'''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside]-7-O-β-D-glucopyranoside (CHEBI:66132) has functional parent trans-4-coumaric acid (CHEBI:32374) kaempferol 3-O-[6-(4-coumaroyl)-β-D-glucosyl-(1→2)-β-D-glucosyl-(1→2)-β-D-glucoside] (CHEBI:31741) has functional parent trans-4-coumaric acid (CHEBI:32374) kaempferol 7-O-(2,3-di-E-p-coumaroyl-α-L-rhamnopyranoside) (CHEBI:66133) has functional parent trans-4-coumaric acid (CHEBI:32374) kaempferol 7-O-(2-E-p-coumaroyl-α-L-rhamnopyranoside) (CHEBI:66134) has functional parent trans-4-coumaric acid (CHEBI:32374) leufolin A (CHEBI:66575) has functional parent trans-4-coumaric acid (CHEBI:32374) leufolin B (CHEBI:66576) has functional parent trans-4-coumaric acid (CHEBI:32374) luzonial A (CHEBI:66598) has functional parent trans-4-coumaric acid (CHEBI:32374) malvidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:75693) has functional parent trans-4-coumaric acid (CHEBI:32374) methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate (CHEBI:86586) has functional parent trans-4-coumaric acid (CHEBI:32374) methyl p-coumarate acetate (CHEBI:86584) has functional parent trans-4-coumaric acid (CHEBI:32374) myrciacitrin IV (CHEBI:66420) has functional parent trans-4-coumaric acid (CHEBI:32374) myricetin 3-O-[(6-O-trans-4-coumaroyl-β-D-glucosyl)-(1→2)-α-L-rhamnoside] (CHEBI:145788) has functional parent trans-4-coumaric acid (CHEBI:32374) pelargonidin 3-(6-p-coumaroyl)glucoside (CHEBI:80475) has functional parent trans-4-coumaric acid (CHEBI:32374) peonidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:75707) has functional parent trans-4-coumaric acid (CHEBI:32374) petunidin 3-O-(6-O-(E)-4-coumaroyl-β-D-glucoside) (CHEBI:75709) has functional parent trans-4-coumaric acid (CHEBI:32374) quercetin 3-O-α-L-[6'''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside] (CHEBI:66285) has functional parent trans-4-coumaric acid (CHEBI:32374) quercetin 3-O-α-L-[6'''-p-coumaroyl-β-D-glucopyranosyl-(1→2)-rhamnopyranoside]-7-O-β-D-glucopyranoside (CHEBI:66286) has functional parent trans-4-coumaric acid (CHEBI:32374) tribuloside (CHEBI:80944) has functional parent trans-4-coumaric acid (CHEBI:32374) trans-4-coumarate (CHEBI:12876) is conjugate base of trans-4-coumaric acid (CHEBI:32374)

IUPAC Name

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

Note: (2004-07-26) The naturally occurring compound has (E) stereochemistry. Both (E) and (Z) isomers are available synthetically.

Synonyms	Sources
(2E)-3-(4-hydroxyphenyl)acrylic acid	ChEBI
(E)-3-(4-hydroxyphenyl)-2-propenoic acid	ChemIDplus
(E)-p-coumaric acid	NIST Chemistry WebBook
(E)-p-hydroxycinnamic acid	ChemIDplus
4'-HYDROXYCINNAMIC ACID	PDBeChem
4-Hydroxycinnamic acid	KEGG COMPOUND
naringeninic acid	NIST Chemistry WebBook
p-Coumaric acid	KEGG COMPOUND
trans-4-hydroxycinnamic acid	ChemIDplus
trans-p-coumaric acid	NIST Chemistry WebBook
trans-p-coumarinic acid	ChemIDplus
trans-p-Hydroxycinnamate	KEGG COMPOUND
trans-p-hydroxycinnamic acid	ChemIDplus

Manual Xrefs	Databases
C00000152	KNApSAcK
C00000580	KNApSAcK
C00811	KEGG COMPOUND
HC4	PDBeChem
HMDB0002035	HMDB
P-Coumaric_acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
2207383	Reaxys Registry Number	Reaxys
2245630	Gmelin Registry Number	Gmelin
501-98-4	CAS Registry Number	ChemIDplus
501-98-4	CAS Registry Number	NIST Chemistry WebBook
7400-08-0	CAS Registry Number	KEGG COMPOUND

Citations

León-Carmona JR, Alvarez-Idaboy JR, Galano A (2012)
On the peroxyl scavenging activity of hydroxycinnamic acid derivatives: mechanisms, kinetics, and importance of the acid-base equilibrium.
Physical chemistry chemical physics : PCCP 14, 12534-12543 [PubMed:22511179]
[show Abstract]

Orr JD, Edwards R, Dixon RA (1993)
Stress Responses in Alfalfa (Medicago sativa L.) (XIV. Changes in the Levels of Phenylpropanoid Pathway Intermediates in Relation to Regulation of L-Phenylalanine Ammonia-Lyase in Elicitor-Treated Cell-Suspension Cultures).
Plant physiology 101, 847-856 [PubMed:12231735]
[show Abstract]

Parry RJ (1975)
Stereochemistry of decarboxylation of trans-4-hydroxycinnamic acid by Aerobacter.
Proceedings of the National Academy of Sciences of the United States of America 72, 1681-1683 [PubMed:1057163]
[show Abstract]

Last Modified

22 October 2024

CHEBI:32374 - trans-4-coumaric acid

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