A secoiridoid polyphenol with diverse biological activities
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Oleocanthal

Item No. 17496

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,4E)-4-formyl-3-(2-oxoethyl)-4-hexenoic acid, 2-(4-hydroxyphenyl)ethyl ester
CAS Number
289030-99-5
Synonyms
  • (–)-Oleocanthal
Molecular Formula
C17H20O5
Formula Weight
304.3
Purity
≥95%
Formulation (Request formulation change)
A neat oil
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleDMSO: Soluble
SMILES
OC1=CC=C(CCOC(C[C@H](CC([H])=O)/C(C([H])=O)=C\C)=O)C=C1
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
InChi Key
VPOVFCBNUOUZGG-VAKDEWRISA-N
Origin
Plant/Olea europaea
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $251

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    Cayman Chemical
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    Product Description

    Oleocanthal is a secoiridoid polyphenol that has been found in O. europaea and has diverse biological activities.1,2,3,4 It inhibits the proliferation of CWR-R1ca, PC3, PC-3M, and DU145 prostate cancer cells (IC50s = 3.59, 0.64, 1.03, and 5.35 µM, respectively).1 Oleocanthal inhibits the growth of L. major promastigotes and amastigotes in vitro (IC50s = 18.7 and 87 µg/ml, respectively) and reduces lymph node parasite burden in a mouse model of leishmaniasis when administered at a dose of 5 mg/kg.2 Oleocanthal (5 mg/kg) reduces hippocampal amyloid-β (Aβ) levels in a TgSwDI transgenic mouse model of Alzheimer’s disease.3 Intragastric administration of oleocanthal (5 mg/kg) decreases serum IL-6 and TNF-α levels and reduces lung cell apoptosis in a chicken model of LPS-induced acute lung injury.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Siddique, A.B., Ebrahim, H.Y., Tajmim, A., et al. Oleocanthal attenuates metastatic castration-resistant prostate cancer progression and recurrence by targeting SMYD2. Cancers (Basel) 14(14), 3542 (2022).

    2. Karampetsou, K., Koutsoni, O.S., Badounas, F., et al. Exploring the immunotherapeutic potential of oleocanthal against murine cutaneous leishmaniasis. Planta Med. 88(9-10), 783-793 (2022).

    3. Qosa, H., Batarseh, Y.S., Mohyeldin, M.M., et al. Oleocanthal enhances amyloid-β clearance from the brains of TgSwDI mice and in vitro across a human blood-brain barrier model. ACS Chem. Neurosci. 6(11), 1849-1859 (2015).

    4. Miao, F., Shan, C., Geng, S., et al. Oleocanthal alleviated lipopolysaccharide-induced acute lung injury in chickens by inhibiting TLR4/NF-κB pathway activation. Poult. Sci. 102(3), 102458 (2022).