oleuropein

Also known as 10-hydroxyoleuropein, 10-hydroxyligstroside

Oleuropein is a glycosylated seco-iridoid, a bitter phenolic compound found in green olive skin, flesh, seeds, and leaves. The term oleuropein is derived from the botanical name of the olive tree, Olea europaea.

In the Vinony graph

Vinony's link graph records 638 inbound references to oleuropein, and connects out to DDT, phthalate ester and (+)-catechin.

It is catalogued under topics including Anti-inflammatory agents, Chembox image size set and ECHA InfoCard ID from Wikidata.

Vinony links it to 22 Wikipedia language editions.

Chemical data

Formula: C25H32O13
Molecular weight: 540.5 g/mol
IUPAC name: methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
SMILES: C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O
InChIKey: RFWGABANNQMHMZ-ZCHJGGQASA-N
XLogP: -0.4
Polar surface area: 202 Å²
H-bond donors: 6
H-bond acceptors: 13
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Has part: hydrogen
Mass: 540.184

Show 6 more facts

found in taxon: Ligustrum lucidum
chemical formula: C₂₅H₃₂O₁₃
isomeric SMILES: C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O
canonical SMILES: CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O
Commons category: Oleuropein
has characteristic: bitterness

Sources (4)

via Wikidata · CC0

~3 min read

Encyclopedic overview

5 sections

Contents

Chemical treatment
Green olive blackening
Research
See also
References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 454372495 | ImageFile=Oleuropein structure.svg | ImageSize=200px | IUPACName = Methyl (2S,3E,4S)-4-{2-[2-(3,4-Dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate | SystematicName = Methyl (2S,3E,4S)-4-{2-[2-(3,4-Dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-pyran-5-carboxylate | OtherNames = 2-(3,4-Dihydroxyphenyl)ethyl [(2S,3E,4S)-3-ethylidene-2-(β-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl]acetate |Section1= |Section2= }}

Excerpted from Wikipedia’s “oleuropein” article, available under the CC BY-SA 4.0 licence.