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12247

Sigma-Aldrich

Oleuropein

≥98.0%

Sinonimo/i:

(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

Formula empirica (notazione di Hill):
C25H32O13
Numero CAS:
32619-42-4
Peso molecolare:
540.51
Numero CE:
251-129-6
Numero MDL:
MFCD16879008
Codice UNSPSC:
12352202
ID PubChem:
329749662
NACRES:
NA.32

Saggio

≥98.0%

Impurezze

≤5.0% water

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Stringa SMILE

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
RFWGABANNQMHMZ-ZCHJGGQASA-N

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Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
BCCG5868
WXBD3682V
WXBD1134V
WXBC9974V
WXBC8225V

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Oleuropeinic acid ≥85% (LC/MS-ELSD)

Sigma-Aldrich

SMB00277

Oleuropeinic acid

Hydroxytyrosol phyproof® Reference Substance

PHL80152

Hydroxytyrosol

Oleocanthal phyproof® Reference Substance

PHL83882

Oleocanthal

Verbascoside ≥99% (HPLC)

Sigma-Aldrich

V4015

Verbascoside

2-(4-Hydroxyphenyl)ethanol 98%

Sigma-Aldrich

188255

2-(4-Hydroxyphenyl)ethanol

Tyrosol phyproof® Reference Substance

PHL80166

Tyrosol

2-(4-Hydroxyphenyl)ethanol analytical standard

Supelco

79058

2-(4-Hydroxyphenyl)ethanol

Verbascoside primary reference standard

00820580

Verbascoside

Luteolin ≥98% (TLC), powder

Sigma-Aldrich

L9283

Luteolin

Sylvia Lee-Huang et al.
Biochemical and biophysical research communications, 354(4), 872-878 (2007-02-06)
We have identified oleuropein (Ole) and hydroxytyrosol (HT) as a unique class of HIV-1 inhibitors from olive leaf extracts effective against viral fusion and integration. We used molecular docking simulation to study the interactions of Ole and HT with viral
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
Oleuropein in olive and its pharmacological effects
Omar SH
Scientia Pharmaceutica, 78(2), 133-154 (2010)
Ioanna Andreadou et al.
The Journal of nutrition, 136(8), 2213-2219 (2006-07-22)
Thgoal of this study was to evaluate the efficacy of the antioxidant olive constituent, oleuropein, on infarct size, oxidative damage, and the metabolic profile in rabbits subjected to ischemia. Oleuropein, 10 or 20 mg/(kg x d), was administered to 8
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