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Merck
CN

SMB00810

Sigma-Aldrich

Oleocanthal

from Olea europaea

别名:

(-)-Oleocanthal

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About This Item

经验公式(希尔记法):
C17H20O5
分子量:
304.34
UNSPSC代码:
12352205
NACRES:
NA.28

生物来源

Olea europaea

方案

≥95%

表单

film

分子量

304.34

溶解性

DMSO: 1 mg/mL, clear, colorless

应用

metabolomics
vitamins, nutraceuticals, and natural products

运输

dry ice

储存温度

−20°C

SMILES字符串

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

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一般描述

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.

应用

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

生化/生理作用

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.

特点和优势

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

其他说明

For additional information on our range of Biochemicals, please complete this form.

储存分类代码

10 - Combustible liquids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Mohamed R Akl et al.
PloS one, 9(5), e97622-e97622 (2014-05-23)
Dysregulation of the Hepatocyte growth factor (HGF)/c-Met signaling axis upregulates diverse tumor cell functions, including cell proliferation, survival, scattering and motility, epithelial-to-mesenchymal transition (EMT), angiogenesis, invasion, and metastasis. (-)-Oleocanthal is a naturally occurring secoiridoid from extra-virgin olive oil, which showed
Kok-Lun Pang et al.
Nutrients, 10(5) (2018-05-08)
Oleocanthal is a minor constituent of olive oil with strong anti-inflammatory activities. Since the pathogenesis of many chronic diseases involves inflammatory and oxidative components, oleocanthal is a promising agent to prevent these conditions. This review aimed to summarise the current
Gary K Beauchamp et al.
Nature, 437(7055), 45-46 (2005-09-02)
Newly pressed extra-virgin olive oil contains oleocanthal--a compound whose pungency induces a strong stinging sensation in the throat, not unlike that caused by solutions of the non-steroidal anti-inflammatory drug ibuprofen. We show here that this similar perception seems to be
Alaa H Abuznait et al.
ACS chemical neuroscience, 4(6), 973-982 (2013-02-19)
Oleocanthal, a phenolic component of extra-virgin olive oil, has been recently linked to reduced risk of Alzheimer's disease (AD), a neurodegenerative disease that is characterized by accumulation of β-amyloid (Aβ) and tau proteins in the brain. However, the mechanism by
Nehad M Ayoub et al.
European journal of pharmacology, 810, 100-111 (2017-06-20)
Luminal breast cancer represents a therapeutic challenge in terms of aggressive disease and emerging resistance to targeted therapy. (-)-Oleocanthal has demonstrated anticancer activity in multiple human cancers. The goal of this study was to explore the effect of (-)-oleocanthal treatment

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