caffeic acid (CHEBI:36281)

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ChEBI Name	caffeic acid

ChEBI ID	CHEBI:36281

Definition	A hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common.

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

Supplier Information	eMolecules:31492408, ZINC000003777403

Download	Molfile XML SDF

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Formula

C9H8O4

Net Charge

Average Mass

180.15740

Monoisotopic Mass

180.04226

InChI

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)

InChIKey

QAIPRVGONGVQAS-UHFFFAOYSA-N

SMILES

OC(=O)C=Cc1ccc(O)c(O)c1

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor A lipoxygenase inhibitor that interferes with the action of arachidonate 15-lipoxygenase (EC 1.13.11.33). EC 2.5.1.18 (glutathione transferase) inhibitor An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of a glutathione transferase (EC 2.5.1.18). EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor A lipoxygenase inhibitor that interferes with the action of arachidonate 5-lipoxygenase (EC 1.13.11.34). EC 3.5.1.98 (histone deacetylase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98).

ChEBI Ontology
Outgoing	caffeic acid (CHEBI:36281) has role antioxidant (CHEBI:22586) caffeic acid (CHEBI:36281) has role EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor (CHEBI:64996) caffeic acid (CHEBI:36281) has role EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor (CHEBI:64964) caffeic acid (CHEBI:36281) has role EC 2.5.1.18 (glutathione transferase) inhibitor (CHEBI:76797) caffeic acid (CHEBI:36281) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115) caffeic acid (CHEBI:36281) has role plant metabolite (CHEBI:76924) caffeic acid (CHEBI:36281) is a catechols (CHEBI:33566) caffeic acid (CHEBI:36281) is a hydroxycinnamic acid (CHEBI:24689)

Incoming	3,4,5-tricaffeoylquinic acid (CHEBI:233498) has functional parent caffeic acid (CHEBI:36281) N¹,N⁵,N¹⁰-tricaffeoyl spermidine (CHEBI:81478) has functional parent caffeic acid (CHEBI:36281) alkyl caffeate ester (CHEBI:65331) has functional parent caffeic acid (CHEBI:36281) caffeoyl-CoA (CHEBI:15518) has functional parent caffeic acid (CHEBI:36281) cis-caffeic acid (CHEBI:17395) is a caffeic acid (CHEBI:36281) trans-caffeic acid (CHEBI:16433) is a caffeic acid (CHEBI:36281)

IUPAC Name

3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Registry Number	Type	Source
2210883	Reaxys Registry Number	Reaxys

Last Modified

13 February 2025