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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
Pricing and availability is not currently available.

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.[1] It is a secoiridoid polyphenol with a structure comprising of a glycosylated ester of elenolic acid with hydroxytyrosol.[1]

Application

Oleuropein has been used:
  • as an anti-inflammatory and antioxidant agent in hepatic steatosis on high-fat diet (HFD) fed mice[2]
  • to evaluate protective effects and antioxidant properties on male reproductive function in mice[3]
  • to study its inhibitory effects on bacterial (E. coli) ATP synthase[4]
  • as an inhibitor of plasminogen activator inhibitor-1 (PAI-1) to test its effect on the proliferation of breast cancer cells[5]

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.[6] Oleuropein has been shown to augment the secretion of noradrenaline and adrenaline in rat. [7]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

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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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
Oleuropein in olive and its pharmacological effects
Omar SH
Scientia Pharmaceutica, 78(2), 133-154 (2010)
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
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
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Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. What is the half-life of this Oleuropein compound, please?

    1 answer

    1. The half life of this product has not been determined as a product specification. However, there is a literature reference studying the stability of this compound: https://www.mdpi.com/2076-3921/10/12/1963

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