SMB00810
Oleocanthal
from Olea europaea
Synonym(s):
(-)-Oleocanthal
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About This Item
Empirical Formula (Hill Notation):
C17H20O5
CAS Number:
Molecular Weight:
304.34
UNSPSC Code:
12352205
NACRES:
NA.28
Recommended Products
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
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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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
For additional information on our range of Biochemicals, please complete this form.
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Customers Also Viewed
Limor Goren et al.
PloS one, 14(8), e0216024-e0216024 (2019-08-15)
(-)-Oleocanthal (oleocanthal) is a phenolic compound found in varying concentrations in extra virgin olive oil oleocanthal has been shown to be active physiologically, benefiting several diseased states by conferring anti-inflammatory and neuroprotective benefits. Recently, we and other groups have demonstrated
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
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
Beatrice Polini et al.
Toxicology in vitro : an international journal published in association with BIBRA, 52, 243-250 (2018-07-01)
Although the anticancer properties of extra virgin olive oil (EVOO) extracts have been recognized, the role of single compounds in non-melanoma skin cancer is still unknown. The in vitro chemopreventive and anticancer action of EVOO extracts and oil-derived compounds in
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