SMB00810

Oleocanthal

from Olea europaea

• Synonyme(s) : (-)-Oleocanthal
• Formule empirique (notation de Hill) : C₁₇H₂₀O₅
• CAS Number: 289030-99-5
• Poids moléculaire : 304.34
• Code UNSPSC : 12352205
• Nomenclature NACRES : NA.28

Propriétés

• Source biologique: Olea europaea
• Essai: ≥95%
• Forme: film
• Poids mol.: 304.34
• Solubilité: DMSO: 1 mg/mL, clear, colorless
• Application(s): metabolomics; vitamins, nutraceuticals, and natural products
• Conditions d'expédition: dry ice
• Température de stockage: −20°C
• Chaîne SMILES: 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
• Clé InChI: VPOVFCBNUOUZGG-VAKDEWRISA-N

Description

Description générale

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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

Autres remarques

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Informations sur la sécurité

• Code de la classe de stockage: 10 - Combustible liquids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable