AdipoGen Life Sciences

Oleacein

CHF 250.00
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AG-CN2-0535-M0055 mgCHF 250.00
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Product Details
Synonyms 3,4-DHPEA-EDA; 3,4-Dihydroxyphenylethanol-elenolic acid dialdehyde; Oleacin
Product Type Chemical
Properties
Formula

C17H20O6

MW 320.3
CAS 149183-75-5
Source/Host Chemicals Isolated from Olea europaea.
Purity Chemicals ≥97% (HPLC)
Appearance Yellow to amber oil.
Solubility Soluble in DMSO, dichloromethane or acetonitrile. Slightly soluble in methanol, ethanol or water (0.1mg/ml).
Identity Determined by 1H-NMR.
Other Product Data

Note: Shown to react spontaneously with water or methanol to give mixtures of hemiacetals or acetals (see Karkoula et al 2012).

InChi Key XLPXUPOZUYGVPD-VMPILDALSA-N
Smiles OC1=C(O)C=CC(CCOC(C[C@H](CC([H])=O)/C(C([H])=O)=C\C)=O)=C1
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Oleacin is a phenolic compound of extra virgin olive oil and has antioxidant, anti-inflammatory, antitumor, antiproliferative, antimicrobial, cardioprotective, antiobesity and antiatherosclerotic properties.
  • In vitro studies showed that oleacein reduces ROS production by f-MLP and PMA-stimulated neutrophils (inhibiting the release of myeloperoxidase).
  • 5-Lipoxygenase (5-LOX) and NF-κB signaling inhibitor.
  • Improves insulin sensitivity in obese mice.
  • Dual substrate-inhibitor of catechol-O-methyltransferase. Inhibits the catalytic activities of nicotinamide N-methyltransferase, ATP-citrate lyase, lysine-specific demethylase 6A and N-methyltransferase 4.
Product References
  1. Simple and hydrolyzable compounds in virgin olive oil. 3. Spectroscopic characterizations of the secoiridoid derivatives: G. Montedoro, et al.; J. Agric. Food Chem. 41, 2228 (1993)
  2. Isolation of an angiotensin converting enzyme (ACE) inhibitor from Olea europaea and Olea lancea: K. Hansen, et al.; Phytomedicine 2, 319 (1996)
  3. Comparison of the concentrations of phenolic compounds in olive oils and other plant oils: Correlation with antimicrobial activity: E. Medina, et al.; J. Agr. Food Chem. 54, 4954 (2006)
  4. Direct Measurement of Oleocanthal and Oleacein Levels in Olive Oil by Quantitative 1H NMR. Establishment of a New Index for the Characterization of Extra Virgin Olive Oils: E. Karkoula, et al.; J. Agric. Food Chem. 60, 11696 (2012)
  5. Inhibition of human neutrophils NEP activity, CD11b/CD18 expression and elastase release by 3,4-dihydroxy-phenylethanol-elenolic acid dialdehyde, oleacein: M.E. Czerwinska, et al.; Food Chem. 153, 1 (2014)
  6. One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor: K. Vougogiannopoulou, et al.; J. Nat. Prod. 77, 441 (2014)
  7. Oleacein. translation from Mediterranean diet to potential antiatherosclerotic drug: M. Naruszewicz, et al.; Curr. Pharm. Des. 21, 1205 (2015) (Review)
  8. Effects of Oleacein on High-Fat Diet-Dependent Steatosis, Weight Gain, and Insulin Resistance in Mice: G.E. Lombardo, et al.; Front. Endocrinol. 9, 116 (2018)
  9. The extra virgin olive oil phenolic oleacein is a dual substrate-inhibitor of catechol-O-methyltransferase: E. Cuyas, et al.; Food Chem. Toxicol. 128, 35 (2019)
  10. Computational de-orphanization of the olive oil biophenol oleacein: Discovery of new metabolic and epigenetic targets: E. Cuyas, et al.; Food Chem. Toxicol. 131, 110529 (2019)
  11. Anti-tumor Activity and Epigenetic Impact of the Polyphenol Oleacein in Multiple Myeloma: G. Juli, et al.; Cancers 11, E990 (2019)
  12. Oleacein Prevents High Fat Diet-Induced Adiposity and Ameliorates Some Biochemical Parameters of Insulin Sensitivity in Mice: S.M. Lepore, et al.; Nutrients 11, E1829 (2019)
  13. The Extra-Virgin Olive Oil Polyphenols Oleocanthal and Oleacein Counteract Inflammation-Related Gene and miRNA Expression in Adipocytes by Attenuating NF-kappaB Activation: S. Carpi, et al.; Nutrients 11, E2855 (2019)
  14. Hydroxytyrosol, Tyrosol and Derivatives and Their Potential Effects on Human Health: A. Karkovic Markovic, et al.; Molecules 24, E2001 (2019)
  15. Oleacein inhibits STAT3, activates the apoptotic machinery, and exerts anti-metastatic effects in the SH-SY5Y human neuroblastoma cells: S. Cirmi, et al. Food Function 11, 3271 (2020)
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