CHEBI:17226 - rosmarinic acid

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ChEBI Name rosmarinic acid
ChEBI ID CHEBI:17226
Definition The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8895, CHEBI:8894, CHEBI:15055, CHEBI:26582
Supplier Information
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Formula C18H16O8
Net Charge 0
Average Mass 360.31480
InChI InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+
InChIKey DOUMFZQKYFQNTF-ZZXKWVIFSA-N
SMILES OC(=O)C(Cc1ccc(O)c(O)c1)OC(=O)\C=C\c1ccc(O)c(O)c1
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): serine proteinase inhibitor
An exogenous or endogenous compound which inhibits serine endopeptidases.
EC 1.1.1.21 (aldehyde reductase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rosmarinic acid (CHEBI:17226) has functional parent trans-caffeic acid (CHEBI:16433)
rosmarinic acid (CHEBI:17226) has role antioxidant (CHEBI:22586)
rosmarinic acid (CHEBI:17226) has role EC 1.1.1.21 (aldehyde reductase) inhibitor (CHEBI:48550)
rosmarinic acid (CHEBI:17226) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
rosmarinic acid (CHEBI:17226) has role peripheral nervous system drug (CHEBI:49110)
rosmarinic acid (CHEBI:17226) has role plant metabolite (CHEBI:76924)
rosmarinic acid (CHEBI:17226) has role serine proteinase inhibitor (CHEBI:48353)
rosmarinic acid (CHEBI:17226) is a carboxylic ester (CHEBI:33308)
rosmarinic acid (CHEBI:17226) is a monocarboxylic acid (CHEBI:25384)
rosmarinic acid (CHEBI:17226) is a phenylpropanoid (CHEBI:26004)
rosmarinic acid (CHEBI:17226) is a polyphenol (CHEBI:26195)
rosmarinic acid (CHEBI:17226) is conjugate acid of rosmarinate (CHEBI:58062)
Incoming (R)-rosmarinic acid (CHEBI:50371) is a rosmarinic acid (CHEBI:17226)
(S)-rosmarinic acid (CHEBI:50372) is a rosmarinic acid (CHEBI:17226)
rosmarinate (CHEBI:58062) is conjugate base of rosmarinic acid (CHEBI:17226)
IUPAC Name
3-(3,4-dihydroxyphenyl)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid
Synonyms Sources
alpha-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy- benzenepropanoic acid ChemIDplus
R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionic acid ChemIDplus
Registry Number Type Source
537-15-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
08 January 2016