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12247

Sigma-Aldrich

Oleuropein

≥98.0%

Synonyme(s) :

(2S,3E,4S)-3-Ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetic acid 2-(3,4-dihydroxyphenyl)ethyl ester

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About This Item

Formule empirique (notation de Hill):
C25H32O13
Numéro CAS:
Poids moléculaire :
540.51
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352202
ID de substance PubChem :
Nomenclature NACRES :
NA.32

Niveau de qualité

Pureté

≥98.0%

Impuretés

≤5.0% water

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Chaîne SMILES 

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)\C(=C\C)[C@@H]1CC(=O)OCCc3ccc(O)c(O)c3

InChI

1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1

Clé InChI

RFWGABANNQMHMZ-ZCHJGGQASA-N

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Description générale

Oleuropein is the major secondary metabolite found in the olive leaf extract. It is a secoiridoid polyphenol with a structure comprising of a glycosylated ester of elenolic acid with hydroxytyrosol.

Application

Oleuropein has been used:
  • as an anti-inflammatory and antioxidant agent in hepatic steatosis on high-fat diet (HFD) fed mice
  • to evaluate protective effects and antioxidant properties on male reproductive function in mice
  • to study its inhibitory effects on bacterial (E. coli) ATP synthase
  • as an inhibitor of plasminogen activator inhibitor-1 (PAI-1) to test its effect on the proliferation of breast cancer cells

Actions biochimiques/physiologiques

Oleuropein has anti-cancer, antimicrobial, antiviral, anti-ischemic and hypolipidemic activities. It functions as a skin protectant and aids anti-aging. Oleuropein is also implicated in anti-platelet aggregation, hypotensive, anti-rheumatic, antipyretic, diuretic and vasodilatory effects. It reduces the risk of coronary artery diseases. Oleuropein has been shown to augment the secretion of noradrenaline and adrenaline in rat.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

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Les clients ont également consulté

Oleuropein, a phenolic compound in extra virgin olive oil, increases uncoupling protein 1 content in brown adipose tissue and enhances noradrenaline and adrenaline secretions in rats
Oi-Kano Y
J. Nutr. Sci. Vitaminol., 54, 363-370 (2008)
Carla Marchetti et al.
Evidence-based complementary and alternative medicine : eCAM, 2015, 908493-908493 (2015-12-23)
Malignant mesothelioma is a poor prognosis cancer in urgent need of alternative therapies. Oleuropein, the major phenolic of olive tree (Olea europaea L.), is believed to have therapeutic potentials for various diseases, including tumors. We obtained an oleuropein-enriched fraction, consisting
W M Walter et al.
Applied microbiology, 26(5), 773-776 (1973-11-01)
Oleuropein, an intensely bitter glucoside, was isolated from green olives. Hydrolysis products obtained from oleuropein in sufficient quantity for further tests were: (i) beta-3,4-dihydroxyphenylethyl alcohol prepared by acid hydrolysis of oleuropein; (ii) elenolic acid obtained by methanolysis of oleuropein, isolation
Oleuropein overrides liver damage in steatotic mice
Santini SJ, et al.,
Journal of functional foods, 65, 103756-103756 (2020)
Amon Amini et al.
International journal of biological macromolecules, 101, 153-164 (2017-03-23)
The naturally occurring olive phenolics tyrosol, hydroxytyrosol, dihydroxyphenylglycol (DHPG), and oleuropein are known to have antioxidant, antitumor, and antibacterial properties. In the current study, we examined whether the antimicrobial properties of tyrosol, hydroxytyrosol, DHPG, and oleuropein were linked to the

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