Merck
All Photos(1)

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
Empirical Formula (Hill Notation):
C25H32O13
CAS Number:
Molecular Weight:
540.51
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥98.0%

impurities

≤5.0% water

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

Packaging

10, 50 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

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.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

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
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
Elena E Tzekaki et al.
Breast cancer research and treatment (2021-01-04)
Elevated expression of PAI-1 has been widely linked with adverse outcomes in a variety of human cancers, such as breast, gastric and ovarian cancers, rendering PAI-1 a prognostic biomarker. As a result, several chemical inhibitors are currently being developed against
Oleuropein overrides liver damage in steatotic mice
Santini SJ, et al.,
Journal of functional foods, 65, 103756-103756 (2020)
Oleuropein in olive and its pharmacological effects
Omar SH
Scientia Pharmaceutica, 78(2), 133-154 (2010)

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