CHEBI:17620 - ferulic acid

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ChEBI Name ferulic acid
ChEBI ID CHEBI:17620
Definition A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:29100, CHEBI:42445, CHEBI:5046, CHEBI:14260, CHEBI:24030
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Formula C10H10O4
Net Charge 0
Average Mass 194.18400
InChI InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChIKey KSEBMYQBYZTDHS-HWKANZROSA-N
SMILES COc1cc(\C=C\C(O)=O)ccc1O
Metabolite of Species Details
Ligusticum porteri (NCBI:54719) Found in root (BTO:0001188). Air-dried and pulverized roots were macerated with CH2Cl2-MeOH(1:1) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
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.
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): MALDI matrix material
A compound used to form the matrix for MALDI (matrix-assisted laser desorption/ionization) mass spectrometry. MALDI matrix materials are crystalline compounds with a fairly low molecular weight, so as to allow facile vaporization, have strong absorption at UV or IR wavelengths (to rapidly and efficiently absorb laser irradiation), generally contain polar groups (enabling them to be used in aqueous solutions) and are frequently acidic (so assisting ionisation of the compound being studied, which is contained within the matrix material).
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ferulic acid (CHEBI:17620) has role anti-inflammatory agent (CHEBI:67079)
ferulic acid (CHEBI:17620) has role antioxidant (CHEBI:22586)
ferulic acid (CHEBI:17620) has role apoptosis inhibitor (CHEBI:68494)
ferulic acid (CHEBI:17620) has role cardioprotective agent (CHEBI:77307)
ferulic acid (CHEBI:17620) has role MALDI matrix material (CHEBI:64345)
ferulic acid (CHEBI:17620) has role plant metabolite (CHEBI:76924)
ferulic acid (CHEBI:17620) is a ferulic acids (CHEBI:24031)
ferulic acid (CHEBI:17620) is conjugate acid of ferulate (CHEBI:29749)
Incoming (−)-DCA-CC (CHEBI:132249) has functional parent ferulic acid (CHEBI:17620)
(−)-DCA-CL (CHEBI:132247) has functional parent ferulic acid (CHEBI:17620)
(+)-DCA-CC (CHEBI:132250) has functional parent ferulic acid (CHEBI:17620)
(+)-DCA-CL (CHEBI:132251) has functional parent ferulic acid (CHEBI:17620)
(2R,3R)-trans-fertaric acid (CHEBI:76116) has functional parent ferulic acid (CHEBI:17620)
(2S,3S)-trans-fertaric acid (CHEBI:76120) has functional parent ferulic acid (CHEBI:17620)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) has functional parent ferulic acid (CHEBI:17620)
1-caffeoyl-5-feruloylquinic acid (CHEBI:88343) has functional parent ferulic acid (CHEBI:17620)
16-feruloyloxypalmitic acid (CHEBI:55330) has functional parent ferulic acid (CHEBI:17620)
2''-O-(6-feruloylglucosyl)isovitexin (CHEBI:75554) has functional parent ferulic acid (CHEBI:17620)
3-O-feruloyl-D-quinic acid (CHEBI:86388) has functional parent ferulic acid (CHEBI:17620)
3-O-feruloylcycloartenol (CHEBI:69436) has functional parent ferulic acid (CHEBI:17620)
4-O-feruloyl-D-quinic acid (CHEBI:18013) has functional parent ferulic acid (CHEBI:17620)
7-O-(6-feruoylglucosyl)isoorientin (CHEBI:75517) has functional parent ferulic acid (CHEBI:17620)
8,5'-diferulic acid (CHEBI:88363) has functional parent ferulic acid (CHEBI:17620)
Cuscuta propenamide 2 (CHEBI:65701) has functional parent ferulic acid (CHEBI:17620)
ent-glycosmisic acid (CHEBI:132257) has functional parent ferulic acid (CHEBI:17620)
N-trans-feruloyl-4ʼ-O-methyldopamine (CHEBI:67378) has functional parent ferulic acid (CHEBI:17620)
N-feruloylserotonin (CHEBI:85158) has functional parent ferulic acid (CHEBI:17620)
N1,N5-dihydroxyferuloyl-N10-sinapoyl spermidine (CHEBI:61516) has functional parent ferulic acid (CHEBI:17620)
O-acetylferulic acid (CHEBI:86582) has functional parent ferulic acid (CHEBI:17620)
trans-methylferulate (CHEBI:67379) has functional parent ferulic acid (CHEBI:17620)
curcumin (CHEBI:3962) has functional parent ferulic acid (CHEBI:17620)
ferulic acid methyl ester monoacetate (CHEBI:86585) has functional parent ferulic acid (CHEBI:17620)
feruloyl-CoA (CHEBI:14261) has functional parent ferulic acid (CHEBI:17620)
feruloylagmatine (CHEBI:75544) has functional parent ferulic acid (CHEBI:17620)
glycosmisic acid (CHEBI:132245) has functional parent ferulic acid (CHEBI:17620)
isovitexin 7-O-[feruloyl]-glucoside (CHEBI:75368) has functional parent ferulic acid (CHEBI:17620)
Diferulic acid (CHEBI:27420) is a ferulic acid (CHEBI:17620)
ferulate (CHEBI:29749) is conjugate base of ferulic acid (CHEBI:17620)
IUPAC Name
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Synonyms Sources
(E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid NIST Chemistry WebBook
(E)-4'-hydroxy-3'-methoxycinnamic acid NIST Chemistry WebBook
(E)-4-Hydroxy-3-methoxycinnamic acid HMDB
(E)-Ferulic acid ChemIDplus
3-(4-Hydroxy-3-methoxyphenyl)propenoic acid NIST Chemistry WebBook
3-methoxy-4-hydroxy-trans-cinnamic acid ChEBI
4-hydroxy-3-methoxycinnamic acid ChEBI
4-Hydroxy-3-methoxycinnamic acid KEGG COMPOUND
Ferulic acid KEGG COMPOUND
trans-4-Hydroxy-3-methoxycinnamic acid ChemIDplus
trans-Ferulic acid ChemIDplus
Database Links Databases
C00002743 KNApSAcK
C01494 KEGG COMPOUND
FER PDBeChem
FERULIC-ACID MetaCyc
Ferulic_Acid Wikipedia
HMDB00954 HMDB
View more database links
Registry Numbers Types Sources
1135-24-6 CAS Registry Number KEGG COMPOUND
1135-24-6 CAS Registry Number ChemIDplus
1570363 Reaxys Registry Number Reaxys
537-98-4 CAS Registry Number ChemIDplus
537-98-4 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11041377 PubMed citation CiteXplore
11982438 PubMed citation CiteXplore
12529986 PubMed citation CiteXplore
15162367 PubMed citation CiteXplore
15309442 PubMed citation CiteXplore
16011737 PubMed citation CiteXplore
16185284 PubMed citation CiteXplore
18582080 PubMed citation CiteXplore
18651237 PubMed citation CiteXplore
18707110 PubMed citation CiteXplore
18795822 PubMed citation CiteXplore
19594750 PubMed citation CiteXplore
8821508 PubMed citation CiteXplore
Last Modified
21 June 2016