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Merck
CN

12247

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
NACRES:
NA.32
PubChem Substance ID:
329749662
UNSPSC Code:
12352202
EC Number:
251-129-6
MDL number:
MFCD16879008

Key Documents

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Product Name

Oleuropein, ≥98.0%

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

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

assay

≥98.0%

impurities

≤5.0% water

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

100

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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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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.

Storage Class

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
WXBF6876V
WXBF3849V
WXBD8487V
WXBF4813V
WXBD7820V

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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
Oleuropein overrides liver damage in steatotic mice
Santini SJ, et al.,
Journal of functional foods, 65, 103756-103756 (2020)
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
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
Oleuropein in olive and its pharmacological effects
Omar SH
Scientia Pharmaceutica, 78(2), 133-154 (2010)
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