Terminology Service < Semantic Lookup Platform

oleocanthal

http://purl.obolibrary.org/obo/CHEBI_85673

A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture.

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Term info

Label

oleocanthal

Synonyms

2-(4-hydroxyphenyl)ethyl (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoate

database cross reference

Subsets

3_STAR

IUPAC NAME

2-(4-hydroxyphenyl)ethyl (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoate [ IUPAC ]

charge

formula

C17H20O5

has obo namespace

chebi_ontology

has related synonym

deacetoxy ligstroside aglycon, (-)-oleocanthal, deacetoxy ligstroside aglycone, (-)-deacetoxy ligstroside aglycon, (-)-deacetoxy ligstroside aglycone

CHEBI:85673

inchi

InChI=1S/C17H20O5/c1-2-14(12-19)15(7-9-18)11-17(21)22-10-8-13-3-5-16(20)6-4-13/h2-6,9,12,15,20H,7-8,10-11H2,1H3/t15-/m0/s1

inchikey

VPOVFCBNUOUZGG-HNNXBMFYSA-N

mass

304.33770

monoisotopicmass

304.13107

smiles

CC=C(C=O)[C@@H](CC=O)CC(=O)OCCc1ccc(O)cc1

Term relations

Subclass of:

carboxylic ester
enal
dialdehyde
phenols
has role some anti-inflammatory agent
has role some cyclooxygenase 2 inhibitor
has role some nutraceutical
has role some antineoplastic agent
has role some antioxidant
has functional parent some 2-(4-hydroxyphenyl)ethanol
has role some cyclooxygenase 1 inhibitor
has role some Hsp90 inhibitor
has role some non-steroidal anti-inflammatory drug
has role some neuroprotective agent
has role some apoptosis inducer
has role some plant metabolite