Oleocanthal | 289030-99-5 | anti-inflammatory

MedKoo Cat#: 581594 | Name: Oleocanthal

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oleocanthal is a phenylethanoid, or a type of natural phenolic compound found in extra-virgin olive oil. Oleocanthal is a tyrosol ester and its chemical structure is related to oleuropein, also found in olive oil. Oleocanthal has been studied for both potential anti-aging and neuroprotective effects in humans.

Chemical Structure

Oleocanthal

CAS#289030-99-5

Theoretical Analysis

MedKoo Cat#: 581594

Name: Oleocanthal

CAS#: 289030-99-5

Chemical Formula: C17H20O5

Exact Mass: 304.1311

Molecular Weight: 304.34

Elemental Analysis: C, 67.09; H, 6.62; O, 26.28

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 650.00	2 Weeks

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Synonym

Oleocanthal; Deacetoxy ligstroside aglycon; (-)-Oleocanthal.

IUPAC/Chemical Name

(3S,4E)-4-Formyl-3-(2-oxoethyl)-4-hexenoic acid 2-(4-hydroxyphenyl)ethyl ester

InChi Key

VPOVFCBNUOUZGG-VAKDEWRISA-N

InChi Code

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

SMILES Code

C/C=C(C=O)\[C@@H](CC=O)CC(OCCC1=CC=C(O)C=C1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oleocanthal is a phenylethanoid, or a type of natural phenolic compound found in extra-virgin olive oil.

In vitro activity:

This study found that OLC (oleocanthal) inhibits cell proliferation and induces apoptotic death as revealed by sub-G1 cell cycle analyses and Annexin-V staining in all lineages analyzed except lung carcinoma cell lines. Hematopoietic tumor cell lines, untested until now, were the most sensitive to OLC treatment, whereas non-transformed cells were significantly resistant to cell death. The specificity of OLC-mediated caspase activation was confirmed by blocking experiments and the use of transfectants overexpressing anti apoptotic genes. OLC triggers typical mediators of the intrinsic apoptotic pathway such as production of reactive oxygen species and mitochondrial membrane depolarization (Δψm). Reference: Food Funct. 2022 Oct 31;13(21):11334-11341. https://pubmed.ncbi.nlm.nih.gov/36254591/

In vivo activity:

This study reports an optimized ex vivo fecal anaerobic fermentation model to study the modulation of GM by the most bioactive EVOO phenolic S-(-)-oleocanthal (OC), and impacts therefrom, focusing on OC biotransformation in the gut. The topmost OC-affected gut bacterial species of the studied mice were compared with those known to be extant in humans and distributions of these bacteria at different human body sites. OC intake caused significant quantitative and qualitative changes to mice GM, which was also comparable with human GM. Reference: Nutrients. 2023 Jan 25;15(3):618. https://pubmed.ncbi.nlm.nih.gov/36771326/

Preparing Stock Solutions

The following data is based on the product molecular weight 304.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Pastorio C, Torres-Rusillo S, Ortega-Vidal J, Jiménez-López MC, Iañez I, Salido S, Santamaría M, Altarejos J, Molina IJ. (-)-Oleocanthal induces death preferentially in tumor hematopoietic cells through caspase dependent and independent mechanisms. Food Funct. 2022 Oct 31;13(21):11334-11341. doi: 10.1039/d2fo01222g. PMID: 36254591. 2. Karampetsou K, Koutsoni OS, Badounas F, Angelis A, Gogou G, Skaltsounis LA, Halabalaki M, Dotsika E. Exploring the Immunotherapeutic Potential of Oleocanthal against Murine Cutaneous Leishmaniasis. Planta Med. 2022 Aug;88(9-10):783-793. doi: 10.1055/a-1843-9788. Epub 2022 Jul 8. PMID: 35803258; PMCID: PMC9343937. 3. Qusa MH, Abdelwahed KS, Hill RA, El Sayed KA. S-(-)-Oleocanthal Ex Vivo Modulatory Effects on Gut Microbiota. Nutrients. 2023 Jan 25;15(3):618. doi: 10.3390/nu15030618. PMID: 36771326; PMCID: PMC9920009. 4/ Miao F, Shan C, Geng S, Ning D. Oleocanthal alleviated lipopolysaccharide-induced acute lung injury in chickens by inhibiting TLR4/NF-κB pathway activation. Poult Sci. 2023 Mar;102(3):102458. doi: 10.1016/j.psj.2022.102458. Epub 2022 Dec 30. PMID: 36640559; PMCID: PMC9842928.

In vitro protocol:

In vivo protocol:

1. Qusa MH, Abdelwahed KS, Hill RA, El Sayed KA. S-(-)-Oleocanthal Ex Vivo Modulatory Effects on Gut Microbiota. Nutrients. 2023 Jan 25;15(3):618. doi: 10.3390/nu15030618. PMID: 36771326; PMCID: PMC9920009. 2. Miao F, Shan C, Geng S, Ning D. Oleocanthal alleviated lipopolysaccharide-induced acute lung injury in chickens by inhibiting TLR4/NF-κB pathway activation. Poult Sci. 2023 Mar;102(3):102458. doi: 10.1016/j.psj.2022.102458. Epub 2022 Dec 30. PMID: 36640559; PMCID: PMC9842928.

1: Goicoechea-Oses E, Ruiz-Aracama A. Usefulness of the 1H NMR Multisuppression Approach for the Global Characterization of Monovarietal Extra- Virgin Olive Oils. Foods. 2024 Jul 22;13(14):2298. doi: 10.3390/foods13142298. PMID: 39063382; PMCID: PMC11276439. 2: Gonçalves M, Vale N, Silva P. Neuroprotective Effects of Olive Oil: A Comprehensive Review of Antioxidant Properties. Antioxidants (Basel). 2024 Jun 24;13(7):762. doi: 10.3390/antiox13070762. PMID: 39061831; PMCID: PMC11274152. 3: Nisticò SP, Greco ME, Amato S, Bennardo L, Zappia E, Pignataro E, Pellacani G. Evaluating the Impact of Oleocanthal and Oleacein on Skin Aging: Results of a Randomized Clinical Study. Medicina (Kaunas). 2024 Jun 6;60(6):947. doi: 10.3390/medicina60060947. PMID: 38929564; PMCID: PMC11205346. 4: Seidita A, Cusimano A, Giuliano A, Meli M, Carroccio A, Soresi M, Giannitrapani L. Oxidative Stress as a Target for Non-Pharmacological Intervention in MAFLD: Could There Be a Role for EVOO? Antioxidants (Basel). 2024 Jun 16;13(6):731. doi: 10.3390/antiox13060731. PMID: 38929170; PMCID: PMC11201095. 5: Torić J, Karković Marković A, Mustać S, Pulitika A, Jakobušić Brala C, Pilepić V. Proton-Coupled Electron Transfer and Hydrogen Tunneling in Olive Oil Phenol Reactions. Int J Mol Sci. 2024 Jun 7;25(12):6341. doi: 10.3390/ijms25126341. PMID: 38928048; PMCID: PMC11203655. 6: Boucheffa S, Kheyar-Keraouche N, Djermouni M, Abelhakim S, Bettihi S, Cheraft N, Berboucha M, Rovellini P, Kelebek H, Tamendjari A. Extra Virgin Olive Oil's Main Components' Antioxidant Activity and in Silico Effect on AKT1. Chem Biodivers. 2024 Jun 24:e202302074. doi: 10.1002/cbdv.202302074. Epub ahead of print. PMID: 38923341. 7: Karagiannis TC, Ververis K, Liang JJ, Pitsillou E, Liu S, Bresnehan SM, Xu V, Wijoyo SJ, Duan X, Ng K, Hung A, Goebel E, El-Osta A. Identification and Evaluation of Olive Phenolics in the Context of Amine Oxidase Enzyme Inhibition and Depression: In Silico Modelling and In Vitro Validation. Molecules. 2024 May 23;29(11):2446. doi: 10.3390/molecules29112446. PMID: 38893322; PMCID: PMC11173677. 8: Antoniadi L, Angelis A, Kostakis IK, Skaltsounis LA. Oxidation Study of Oleocanthal and Oleacein Induced by Oxone. Planta Med. 2024 Jun;90(7-08):554-560. doi: 10.1055/a-2235-0009. Epub 2024 Jun 6. PMID: 38843795. 9: De Stefanis D, Balestrini A, Costelli P. Oleocanthal Protects C2C12 Myotubes against the Pro-Catabolic and Anti-Myogenic Action of Stimuli Able to Induce Muscle Wasting In Vivo. Nutrients. 2024 Apr 26;16(9):1302. doi: 10.3390/nu16091302. PMID: 38732549; PMCID: PMC11085360. 10: Marrero AD, Quesada AR, Martínez-Poveda B, Medina MÁ. Anti-Cancer, Anti- Angiogenic, and Anti-Atherogenic Potential of Key Phenolic Compounds from Virgin Olive Oil. Nutrients. 2024 Apr 25;16(9):1283. doi: 10.3390/nu16091283. PMID: 38732529; PMCID: PMC11085358. 11: Di Pietro M, Filardo S, Mattioli R, Bozzuto G, Raponi G, Mosca L, Sessa R. Anti-Biofilm Activity of Oleacein and Oleocanthal from Extra-Virgin Olive Oil toward Pseudomonas aeruginosa. Int J Mol Sci. 2024 May 6;25(9):5051. doi: 10.3390/ijms25095051. PMID: 38732269; PMCID: PMC11084407. 12: Cho J, Bejaoui M, Tominaga K, Isoda H. Comparative Analysis of Olive-Derived Phenolic Compounds' Pro-Melanogenesis Effects on B16F10 Cells and Epidermal Human Melanocytes. Int J Mol Sci. 2024 Apr 19;25(8):4479. doi: 10.3390/ijms25084479. PMID: 38674064; PMCID: PMC11050296. 13: Tsolis T, Kyriakou D, Sifnaiou E, Thomos D, Glykos D, Tsiafoulis CG, Garoufis A. NMR Analysis of Extra Virgin Olive Oil of the Epirus Region of Greece with Emphasis on Selected Phenolic Compounds. Molecules. 2024 Mar 1;29(5):1111. doi: 10.3390/molecules29051111. PMID: 38474623; PMCID: PMC10934859. 14: Akcan T. Investigating the Quality and Purity Profiles of Olive Oils from Diverse Regions in Selçuk, İzmir. Molecules. 2024 Feb 29;29(5):1104. doi: 10.3390/molecules29051104. PMID: 38474614; PMCID: PMC10933960. 15: González-Acedo A, Illescas-Montes R, de Luna-Bertos E, Ruiz C, Ramos- Torrecillas J, García-Martínez O, Melguizo-Rodríguez L. Extra Virgin Olive Oil Phenolic Compounds Modulate the Gene Expression of Biomarkers Involved in Fibroblast Proliferation and Differentiation. Genes (Basel). 2024 Jan 28;15(2):173. doi: 10.3390/genes15020173. PMID: 38397163; PMCID: PMC10887570. 16: Filardo S, Roberto M, Di Risola D, Mosca L, Di Pietro M, Sessa R. Olea europaea L-derived secoiridoids: Beneficial health effects and potential therapeutic approaches. Pharmacol Ther. 2024 Feb;254:108595. doi: 10.1016/j.pharmthera.2024.108595. Epub 2024 Jan 30. PMID: 38301769. 17: Katsa ME, Ketselidi K, Kalliostra M, Ioannidis A, Rojas Gil AP, Diamantakos P, Melliou E, Magiatis P, Nomikos T. Acute Antiplatelet Effects of an Oleocanthal-Rich Olive Oil in Type II Diabetic Patients: A Postprandial Study. Int J Mol Sci. 2024 Jan 11;25(2):908. doi: 10.3390/ijms25020908. PMID: 38255980; PMCID: PMC10815739. 18: Infante R, Infante M, Pastore D, Pacifici F, Chiereghin F, Malatesta G, Donadel G, Tesauro M, Della-Morte D. An Appraisal of the Oleocanthal-Rich Extra Virgin Olive Oil (EVOO) and Its Potential Anticancer and Neuroprotective Properties. Int J Mol Sci. 2023 Dec 10;24(24):17323. doi: 10.3390/ijms242417323. PMID: 38139152; PMCID: PMC10744258. 19: González-Rodríguez M, Ait Edjoudi D, Cordero-Barreal A, Farrag M, Varela- García M, Torrijos-Pulpón C, Ruiz-Fernández C, Capuozzo M, Ottaiano A, Lago F, Pino J, Farrag Y, Gualillo O. Oleocanthal, an Antioxidant Phenolic Compound in Extra Virgin Olive Oil (EVOO): A Comprehensive Systematic Review of Its Potential in Inflammation and Cancer. Antioxidants (Basel). 2023 Dec 14;12(12):2112. doi: 10.3390/antiox12122112. PMID: 38136231; PMCID: PMC10741130. 20: Asgarshamsi MH, Dehkordi MM, Nazifi SMR, Zborowski KK. Theoretical Evaluation of Oleocanthal Reactive Centers. Curr Drug Metab. 2023;24(11):756-762. doi: 10.2174/0113892002276499231201094142. PMID: 38099536.