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Merck
CN

12247

Sigma-Aldrich

Oleuropein

≥98.0%

Synonym(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

Empirical Formula (Hill Notation):
C25H32O13
CAS Number:
32619-42-4
Molecular Weight:
540.51
EC Number:
251-129-6
MDL number:
MFCD16879008
UNSPSC Code:
12352202
PubChem Substance ID:
329749662
NACRES:
NA.32

Key Documents

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Quality Level

100

Assay

≥98.0%

impurities

≤5.0% water

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

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

InChI key

RFWGABANNQMHMZ-ZCHJGGQASA-N

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General description

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

Biochem/physiol Actions

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF3849V
WXBD8487V
WXBF4813V
WXBD7820V
BCCG5868

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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, 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)
Oleuropein in olive and its pharmacological effects
Omar SH
Scientia Pharmaceutica, 78(2), 133-154 (2010)
Ayoob Rostamzadeh et al.
Heliyon, 6(4), e03785-e03785 (2020-04-28)
Spermatogenesis is a complicated process in which sperm is susceptible to various chemotherapy drugs such as cyclophosphamide (CP). As olive leaf extract (OLE) and its active ingredient, oleuropein, have variousantioxidant, anti-apoptotic, and anti-inflammatory properties the aim of the present study
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
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