SMB00810

Oleocanthal

from Olea europaea

• Synonyma: (-)-Oleocanthal
• Empirický vzorec (Hillův zápis): C₁₇H₂₀O₅
• Číslo CAS: 289030-99-5
• Molekulová hmotnost: 304.34
• UNSPSC Code: 12352205
• NACRES: NA.28

Vlastnosti

• biological source: Olea europaea
• assay: ≥95%
• form: film
• mol wt: 304.34
• solubility: DMSO: 1 mg/mL, clear, colorless
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: O(CCc1ccc(cc1)O)C(=O)C[C@H](CC=O)\C(=C/C)\C=O
• InChI: 1S/C17H20O5/c1-2-14(12-19)15(7-9-18)11-17(21)22-10-8-13-3-5-16(20)6-4-13/h2-6,9,12,15,20H,7-8,10-11H2,1H3/b14-2-/t15-/m0/s1
• InChI key: VPOVFCBNUOUZGG-VAKDEWRISA-N

Popis

General description

Oleocanthal, a secoiridoid, a cyclopentane monoterpene, and a member of phenols, is a bioactive natural compound commonly derived from Olive oil (Olea europaea). Current research suggests that this metabolite acts as an inhibitor and may exhibit diverse biological activities, including anti-inflammatory, neuroprotective, apoptosis-inducing, antioxidant, antimalarial, and antineoplastic properties.

Application

Oleocanthal is a natural product derived from plant source that finds application in compound screening libraries, metabolomics, phytochemical, and drug discovery research.

Biochem/physiol Actions

Oleocanthal is one of the important polyphenols of olive oil well-known for its biological properties and health benefits. It exerts anti-inflammatory activity due to its dose-dependent inhibition of cyclooxygenase (COX-1, COX-2) enzymes in the prostaglandin biosynthesis in the same pathway as Ibuprofen. Oleocanthal is a potent anti-cancer agent, its treatment demonstrates inhibition of proliferation, migration, and invasion of various human breast cancer, prostate cancer, and multiple myeloma cells. In non-melanoma skin cancer, it reduces cell viability and migration, through inhibition of Erk and Akt phosphorylation and suppression of B-Raf expression. Oleocanthal was found to modulate estrogen receptor expression in luminal breast cancer and acts synergistically with tamoxifen treatment. It also elicits neuroprotective properties by inhibiting the formation of neurofibrillary tangles, a key hallmark in the pathogenesis of Alzheimer′s disease. Oleocanthal has also been reported to increase Amyloid-β transport across the blood-brain barrier via P-glycoprotein induction. It was found that it acts synergistically with Donepezil, an acetylcholine esterase inhibitor approved for use for all Alzheimer′s disease stages. Oleuropein displays anti-leishmanial activity when added in vitro and in vivo, in experimental models of Leishmania infection.

Features and Benefits

• High quality compound suitable for multiple research applications
• Compatible with HPLC and mass spectrometry techniques

Other Notes

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Bezpečnostní informace

• Skladovací třída: 10 - Combustible liquids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable