CHEBI:17620 - trans-ferulic acid

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ChEBI Name trans-ferulic acid
ChEBI ID CHEBI:17620
ChEBI ASCII Name trans-ferulic acid
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
Supplier Information eMolecules:29909223
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Wikipedia License
Delphinidin (also delphinidine) is an anthocyanidin, a primary plant pigment, and also an antioxidant. Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape variety Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates, and bilberries. Delphinidin, like nearly all other anthocyanidins, is pH-sensitive, i.e. a natural pH indicator, and changes from blue in basic solution to red in acidic solution.
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Formula C10H10O4
Net Charge 0
Average Mass 194.18400
Monoisotopic Mass 194.05791
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:txid54719) 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.
(via ferulic acid )
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.
(via ferulic acid )
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.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
(via ferulic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing trans-ferulic acid (CHEBI:17620) has role anti-inflammatory agent (CHEBI:67079)
trans-ferulic acid (CHEBI:17620) has role antioxidant (CHEBI:22586)
trans-ferulic acid (CHEBI:17620) has role apoptosis inhibitor (CHEBI:68494)
trans-ferulic acid (CHEBI:17620) has role cardioprotective agent (CHEBI:77307)
trans-ferulic acid (CHEBI:17620) has role MALDI matrix material (CHEBI:64345)
trans-ferulic acid (CHEBI:17620) has role plant metabolite (CHEBI:76924)
trans-ferulic acid (CHEBI:17620) is a ferulic acid (CHEBI:193350)
trans-ferulic acid (CHEBI:17620) is conjugate acid of trans-ferulate (CHEBI:29749)
Incoming (−)-DCA-CC (CHEBI:132249) has functional parent trans-ferulic acid (CHEBI:17620)
(−)-DCA-CL (CHEBI:132247) has functional parent trans-ferulic acid (CHEBI:17620)
(+)-DCA-CC (CHEBI:132250) has functional parent trans-ferulic acid (CHEBI:17620)
(+)-DCA-CL (CHEBI:132251) has functional parent trans-ferulic acid (CHEBI:17620)
(2E)-3-(4-{[1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(sulfooxy)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoic acid (CHEBI:91208) has functional parent trans-ferulic acid (CHEBI:17620)
(2E)-3-(4-{[3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-(sulfooxy)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoic acid (CHEBI:91206) has functional parent trans-ferulic acid (CHEBI:17620)
(2E)-3-[4-({1,3-dihydroxy-1-[3-methoxy-4-(sulfooxy)phenyl]propan-2-yl}oxy)-3-methoxyphenyl]prop-2-enoic acid (CHEBI:91205) has functional parent trans-ferulic acid (CHEBI:17620)
(2R,3R)-trans-fertaric acid (CHEBI:76116) has functional parent trans-ferulic acid (CHEBI:17620)
(2R,3S)-glycosmisic acid (CHEBI:132245) has functional parent trans-ferulic acid (CHEBI:17620)
(2S,3R)-glycosmisic acid (CHEBI:132257) has functional parent trans-ferulic acid (CHEBI:17620)
(2S,3S)-trans-fertaric acid (CHEBI:76120) has functional parent trans-ferulic acid (CHEBI:17620)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) has functional parent trans-ferulic acid (CHEBI:17620)
1-O-feruloyl-β-D-glucose (CHEBI:81321) has functional parent trans-ferulic acid (CHEBI:17620)
1-caffeoyl-5-feruloylquinic acid (CHEBI:88343) has functional parent trans-ferulic acid (CHEBI:17620)
1-feruloyl-sn-glycerol (CHEBI:149477) has functional parent trans-ferulic acid (CHEBI:17620)
16-feruloyloxypalmitic acid (CHEBI:55330) has functional parent trans-ferulic acid (CHEBI:17620)
2''-O-(6-feruloylglucosyl)isovitexin (CHEBI:75554) has functional parent trans-ferulic acid (CHEBI:17620)
3-O-feruloyl-D-quinic acid (CHEBI:86388) has functional parent trans-ferulic acid (CHEBI:17620)
3-O-feruloylcycloartenol (CHEBI:69436) has functional parent trans-ferulic acid (CHEBI:17620)
4-O-β-D-glucosyl-trans-ferulic acid (CHEBI:139435) has functional parent trans-ferulic acid (CHEBI:17620)
4-O-feruloyl-D-quinic acid (CHEBI:18013) has functional parent trans-ferulic acid (CHEBI:17620)
7-O-(6-feruoylglucosyl)isoorientin (CHEBI:75517) has functional parent trans-ferulic acid (CHEBI:17620)
8,5'-diferulic acid (CHEBI:88363) has functional parent trans-ferulic acid (CHEBI:17620)
Cuscuta propenamide 2 (CHEBI:65701) has functional parent trans-ferulic acid (CHEBI:17620)
N-trans-feruloyl-4ʼ-O-methyldopamine (CHEBI:67378) has functional parent trans-ferulic acid (CHEBI:17620)
N-feruloylserotonin (CHEBI:85158) has functional parent trans-ferulic acid (CHEBI:17620)
N1,N5,N10-tris-(E)-feruloyl spermidine (CHEBI:232326) has functional parent trans-ferulic acid (CHEBI:17620)
N1,N5-dihydroxyferuloyl-N10-sinapoyl spermidine (CHEBI:61516) has functional parent trans-ferulic acid (CHEBI:17620)
O-acetylferulic acid (CHEBI:86582) has functional parent trans-ferulic acid (CHEBI:17620)
trans-methylferulate (CHEBI:67379) has functional parent trans-ferulic acid (CHEBI:17620)
avenanthramide B (CHEBI:167489) has functional parent trans-ferulic acid (CHEBI:17620)
curcumin (CHEBI:3962) has functional parent trans-ferulic acid (CHEBI:17620)
ferulic acid 4-sulfate (CHEBI:133508) has functional parent trans-ferulic acid (CHEBI:17620)
feruloyl-CoA (CHEBI:14261) has functional parent trans-ferulic acid (CHEBI:17620)
feruloylagmatine (CHEBI:75544) has functional parent trans-ferulic acid (CHEBI:17620)
feruloylglycoside (CHEBI:142427) has functional parent trans-ferulic acid (CHEBI:17620)
glycosmisic acid (CHEBI:91209) has functional parent trans-ferulic acid (CHEBI:17620)
isovitexin 7-O-[feruloyl]-glucoside (CHEBI:75368) has functional parent trans-ferulic acid (CHEBI:17620)
methyl 4-acetoxy-3-methoxycinnamate (CHEBI:86585) has functional parent trans-ferulic acid (CHEBI:17620)
Diferulic acid (CHEBI:27420) is a trans-ferulic acid (CHEBI:17620)
trans-ferulate (CHEBI:29749) is conjugate base of trans-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
Manual Xrefs Databases
C00002743 KNApSAcK
C01494 KEGG COMPOUND
FER PDBeChem
FERULIC-ACID MetaCyc
Ferulic_Acid Wikipedia
HMDB0000954 HMDB
View more database links
Registry Numbers Types Sources
1570363 Reaxys Registry Number Reaxys
537-98-4 CAS Registry Number ChemIDplus
537-98-4 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
11041377 PubMed citation Europe PMC
11982438 PubMed citation Europe PMC
12529986 PubMed citation Europe PMC
15162367 PubMed citation Europe PMC
15309442 PubMed citation Europe PMC
16011737 PubMed citation Europe PMC
16185284 PubMed citation Europe PMC
18582080 PubMed citation Europe PMC
18651237 PubMed citation Europe PMC
18707110 PubMed citation Europe PMC
18795822 PubMed citation Europe PMC
19594750 PubMed citation Europe PMC
8821508 PubMed citation Europe PMC
Last Modified
22 October 2024