Oleocanthal
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MedKoo CAT#: 581594

CAS#: 289030-99-5

Description: 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.


Chemical Structure

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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
5.0mg USD 1980.0 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

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.

Recalculate based on batch purity %
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

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1: Miho H, Díez CM, Mena-Bravo A, Sánchez de Medina V, Moral J, Melliou E, Magiatis P, Rallo L, Barranco D, Priego-Capote F. Cultivar influence on variability in olive oil phenolic profiles determined through an extensive germplasm survey. Food Chem. 2018 Nov 15;266:192-199. doi: 10.1016/j.foodchem.2018.06.002. Epub 2018 Jun 4. PubMed PMID: 30381176.

2: Diez-Bello R, Jardin I, Lopez JJ, El Haouari M, Ortega-Vidal J, Altarejos J, Salido GM, Salido S, Rosado JA. (-) Oleocanthal inhibits proliferation and migration by modulating Ca(2+) entry through TRPC6 in breast cancer cells. Biochim Biophys Acta Mol Cell Res. 2018 Oct 12. pii: S0167-4889(18)30451-8. doi: 10.1016/j.bbamcr.2018.10.010. [Epub ahead of print] PubMed PMID: 30321616.

3: Scotece M, Conde J, Abella V, López V, Francisco V, Ruiz C, Campos V, Lago F, Gomez R, Pino J, Gualillo O. Oleocanthal Inhibits Catabolic and Inflammatory Mediators in LPS-Activated Human Primary Osteoarthritis (OA) Chondrocytes Through MAPKs/NF-κB Pathways. Cell Physiol Biochem. 2018;49(6):2414-2426. doi: 10.1159/000493840. Epub 2018 Sep 27. PubMed PMID: 30261513.

4: Segura-Carretero A, Curiel JA. Current Disease-Targets for Oleocanthal as Promising Natural Therapeutic Agent. Int J Mol Sci. 2018 Sep 24;19(10). pii: E2899. doi: 10.3390/ijms19102899. Review. PubMed PMID: 30250008; PubMed Central PMCID: PMC6213726.

5: Czerwińska ME, Gąsińska E, Leśniak A, Krawczyk P, Kiss AK, Naruszewicz M, Bujalska-Zadrożny M. Inhibitory effect of Ligustrum vulgare leaf extract on the development of neuropathic pain in a streptozotocin-induced rat model of diabetes. Phytomedicine. 2018 Oct 1;49:75-82. doi: 10.1016/j.phymed.2018.06.006. Epub 2018 Jun 11. PubMed PMID: 30217264.

6: Koutsoni OS, Karampetsou K, Kyriazis ID, Stathopoulos P, Aligiannis N, Halabalaki M, Skaltsounis LA, Dotsika E. Evaluation of total phenolic fraction derived from extra virgin olive oil for its antileishmanial activity. Phytomedicine. 2018 Aug 1;47:143-150. doi: 10.1016/j.phymed.2018.04.030. Epub 2018 May 10. PubMed PMID: 30166099.

7: Giusti L, Angeloni C, Barbalace MC, Lacerenza S, Ciregia F, Ronci M, Urbani A, Manera C, Digiacomo M, Macchia M, Mazzoni MR, Lucacchini A, Hrelia S. A Proteomic Approach to Uncover Neuroprotective Mechanisms of Oleocanthal against Oxidative Stress. Int J Mol Sci. 2018 Aug 8;19(8). pii: E2329. doi: 10.3390/ijms19082329. PubMed PMID: 30096819; PubMed Central PMCID: PMC6121693.

8: Polini B, Digiacomo M, Carpi S, Bertini S, Gado F, Saccomanni G, Macchia M, Nieri P, Manera C, Fogli S. Oleocanthal and oleacein contribute to the in vitro therapeutic potential of extra virgin oil-derived extracts in non-melanoma skin cancer. Toxicol In Vitro. 2018 Oct;52:243-250. doi: 10.1016/j.tiv.2018.06.021. Epub 2018 Jun 28. PubMed PMID: 29959992.

9: Agrawal K, Melliou E, Li X, Pedersen TL, Wang SC, Magiatis P, Newman JW, Holt RR. Oleocanthal-rich extra virgin olive oil demonstrates acute anti-platelet effects in healthy men in a randomized trial. J Funct Foods. 2017 Sep;36:84-93. doi: 10.1016/j.jff.2017.06.046. Epub 2017 Jul 3. PubMed PMID: 29904393; PubMed Central PMCID: PMC5995573.

10: Tsolakou A, Diamantakos P, Kalaboki I, Mena-Bravo A, Priego-Capote F, Abdallah IM, Kaddoumi A, Melliou E, Magiatis P. Oleocanthalic Acid, a Chemical Marker of Olive Oil Aging and Exposure to a High Storage Temperature with Potential Neuroprotective Activity. J Agric Food Chem. 2018 Jul 18;66(28):7337-7346. doi: 10.1021/acs.jafc.8b00561. Epub 2018 Jul 3. PubMed PMID: 29902916.

11: Celano R, Piccinelli AL, Pugliese A, Carabetta S, di Sanzo R, Rastrelli L, Russo M. Insights into the Analysis of Phenolic Secoiridoids in Extra Virgin Olive Oil. J Agric Food Chem. 2018 Jun 20;66(24):6053-6063. doi: 10.1021/acs.jafc.8b01751. Epub 2018 Jun 6. PubMed PMID: 29800514.

12: Pang KL, Chin KY. The Biological Activities of Oleocanthal from a Molecular Perspective. Nutrients. 2018 May 6;10(5). pii: E570. doi: 10.3390/nu10050570. Review. PubMed PMID: 29734791; PubMed Central PMCID: PMC5986450.

13: Kalogiouri NP, Aalizadeh R, Thomaidis NS. Application of an advanced and wide scope non-target screening workflow with LC-ESI-QTOF-MS and chemometrics for the classification of the Greek olive oil varieties. Food Chem. 2018 Aug 1;256:53-61. doi: 10.1016/j.foodchem.2018.02.101. Epub 2018 Feb 21. PubMed PMID: 29606472.

14: Johnson R, Melliou E, Zweigenbaum J, Mitchell AE. Quantitation of Oleuropein and Related Phenolics in Cured Spanish-Style Green, California-Style Black Ripe, and Greek-Style Natural Fermentation Olives. J Agric Food Chem. 2018 Mar 7;66(9):2121-2128. doi: 10.1021/acs.jafc.7b06025. Epub 2018 Feb 20. PubMed PMID: 29424233.

15: Batarseh YS, Kaddoumi A. Oleocanthal-rich extra-virgin olive oil enhances donepezil effect by reducing amyloid-β load and related toxicity in a mouse model of Alzheimer's disease. J Nutr Biochem. 2018 May;55:113-123. doi: 10.1016/j.jnutbio.2017.12.006. Epub 2017 Dec 27. PubMed PMID: 29413486; PubMed Central PMCID: PMC5936648.

16: Morrone L, Neri L, Cantini C, Alfei B, Rotondi A. Study of the combined effects of ripeness and production area on Bosana oil's quality. Food Chem. 2018 Apr 15;245:1098-1104. doi: 10.1016/j.foodchem.2017.11.061. Epub 2017 Nov 16. PubMed PMID: 29287327.

17: Mete M, Aydemir I, Unsal UU, Collu F, Vatandas G, Gurcu B, Duransoy YK, Taneli F, Tugrul MI, Selcuki M. Neuroprotective Effects of Oleocanthal, A Compound in Virgin Olive Oil, in A Rat Model of Traumatic Brain Injury. Turk Neurosurg. 2017 Nov 1. doi: 10.5137/1019-5149.JTN.21417-17.2. [Epub ahead of print] PubMed PMID: 29204981.

18: Angeloni C, Malaguti M, Barbalace MC, Hrelia S. Bioactivity of Olive Oil Phenols in Neuroprotection. Int J Mol Sci. 2017 Oct 25;18(11). pii: E2230. doi: 10.3390/ijms18112230. Review. PubMed PMID: 29068387; PubMed Central PMCID: PMC5713200.

19: Chin KY, Pang KL. Therapeutic Effects of Olive and Its Derivatives on Osteoarthritis: From Bench to Bedside. Nutrients. 2017 Sep 26;9(10). pii: E1060. doi: 10.3390/nu9101060. Review. PubMed PMID: 28954409; PubMed Central PMCID: PMC5691677.

20: Cusimano A, Balasus D, Azzolina A, Augello G, Emma MR, Di Sano C, Gramignoli R, Strom SC, McCubrey JA, Montalto G, Cervello M. Oleocanthal exerts antitumor effects on human liver and colon cancer cells through ROS generation. Int J Oncol. 2017 Aug;51(2):533-544. doi: 10.3892/ijo.2017.4049. Epub 2017 Jun 21. PubMed PMID: 28656311.