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O8889

Sigma-Aldrich

Oleuropein

≥80% (HPLC)

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About This Item

Formule empirique (notation de Hill):
C25H32O13
Numéro CAS:
32619-42-4
Poids moléculaire :
540.51
Numéro CE :
251-129-6
Numéro MDL:
MFCD16879008
Code UNSPSC :
12352200
ID de substance PubChem :
329818929
Nomenclature NACRES :
NA.25

Description

Synthetic

Pureté

≥80% (HPLC)

Forme

powder

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

room temp

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

Catégories apparentées

Description générale

Oleuropein is one of the main phenolic compounds of olive oil, which gives a bitter and pungent taste to the extra-virgin olive oil. It is a type of secoiridoids and an ester of 3-Hydroxytyrosol with an oleosidic skeleton. Oleuropein is found in the oil and fruits of Olea europaea and also in genera belonging to the Oleaceae family.

Application

Oleuropein has been used:
  • as an anticancer agent to test its effect on different apoptotic pathway regulators in two breast cancer cell lines (MCF7 and MDA-MB-231) in cell viability assay
  • as an antioxidant to test its effect on the hydrogen peroxide (H2O2)-induced premature senescence in human fibroblast cell lines
  • to test its anticancer properties on the cell viability, cisplatin resistance, and apoptosis in two ovarian cell lines (A2780S and A2780/CP cell lines)
  • as a model antioxidant to analyze the quenching activity of 2,2-diphenyl-1-picrylhydrazyl (DPPH) in different solvents

Actions biochimiques/physiologiques

Oleuropein has many pharmacological benefits with its antioxidant, anti-inflammatory, antimicrobial, antiviral, hypoglycemic, hypolipidemic, neuroprotective, and anti-aging effects. It has shown antimycoplasmal activity against Mycoplasma strains in in vitro studies.
Phenolic constituent of olive oil. Contributes to anticancer properties of olive oil. Oleuropein and its metabolite, hydroxytyrosol, inhibit the rate of cancer cell proliferation and
induce cancer cell apoptosis.

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

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Syed Haris Omar
Scientia pharmaceutica, 78(2), 133-154 (2010-12-24)
Olive from Olea europaea is native to the Mediterranean region and, both the oil and the fruit are some of the main components of the Mediterranean diet. The main active constituents of olive oil include oleic acid, phenolic constituents, and
Pio Maria Furneri et al.
International journal of antimicrobial agents, 20(4), 293-296 (2002-10-19)
The activity of oleuropein, a phenolic glycoside contained in olive oil, was investigated in vitro against Mycoplasma hominis, Mycoplasma fermentans, Mycoplasma pneumoniae and Mycoplasma pirum. Oleuropein inhibited mycoplasmas at concentrations from 20 to 320 mg/l. The MICs of oleuropein to
Tjaša Prevc et al.
Talanta, 109, 13-19 (2013-04-27)
The rate of reaction of phenolic antioxidants with DPPH depends on solvent composition. The rate constants can differ by more than two orders of magnitude for the same phenolic compound. Reactions are faster in alcohols than in ethyl acetate that
Somayeh Hashemi Sheikhshabani et al.
Life sciences, 278, 119525-119525 (2021-04-25)
Despite many attempts to treat ovarian cancer, 13,940 individuals perish annually due to this disease worldwide. Chemotherapy is the main approach to ovarian cancer treatment, but the development of drug resistance is a major obstacle to the successful treatment. Oleuropein
Samira Asgharzade et al.
European journal of pharmacology, 886, 173509-173509 (2020-09-06)
In spite of advancements in breast cancer therapy, this disease is still one of the significant causes of women fatalities globally. Dysregulation of miRNA plays a pivotal role in the initiation and progression of cancer. Therefore, the administration of herbal
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