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O8889

Sigma-Aldrich

Oleuropein

≥80% (HPLC)

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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:
12352200
PubChem Substance ID:
329818929
NACRES:
NA.25

description

Synthetic

assay

≥80% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

room temp

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

Related Categories

General description

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

Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Aderonke Oyetunji et al.
Psychiatry research, 284, 112769-112769 (2020-01-22)
Postpartum stress has been shown to have an association with infant growth, nutrition, bonding, temperament and ultimately childhood mental wellbeing. When persistent, recurring or chronic, it can negatively impact infant outcome, including the subscales of mental wellbeing such as growth
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
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