A soluble epoxide hydrolase inhibitor
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N-Benzyl Linoleamide

Item No. 33358

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(9Z,12Z)-N-(phenylmethyl)-9,12-octadecadienamide
CAS Number
18286-71-0
Molecular Formula
C25H39NO
Formula Weight
369.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
SMILES
CCCCC/C=C\C/C=C\CCCCCCCC(NCC1=CC=CC=C1)=O
InChi Code
InChI=1S/C25H39NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-25(27)26-23-24-20-17-16-18-21-24/h6-7,9-10,16-18,20-21H,2-5,8,11-15,19,22-23H2,1H3,(H,26,27)/b7-6-,10-9-
InChi Key
YJWLCIANOBCQGW-HZJYTTRNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $153

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    10 mg

    $268

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    25 mg

    $587

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    Product Description

    N-Benzyl linoleamide is an inhibitor of soluble epoxide hydrolase (sEH; IC50s = 0.155, 0.041, and 0.044 µM for the human, rat, and mouse enzymes, respectively).1 It is selective for sEH over fatty acid amide hydrolase (FAAH; IC50 = 10.8 µM for the human enzyme). N-Benzyl linoleamide also inhibits the production of NF-κB (IC50 = 8.80 µM) and activates nuclear factor erythroid 2-related factor 2 (Nrf2; EC50 = 35.24 µM in a transactivation assay) in Neuro2a murine neuroblastoma cells.2 It increases the paw withdrawal threshold in a mouse model of LPS-induced inflammatory pain when administered at a dose of 100 mg/kg.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Singh, N., Barnych, B., Morisseau, C., et al. N‑Benzyl-linoleamide, a constituent of Lepidium meyenii (maca), is an orally bioavailable soluble epoxide hydrolase inhibitor that alleviates inflammatory pain. J. Nat. Prod. 83(12), 3689-3697 (2020).

    2. Ticona, L.A., Pérez, V.T., Serban, A.M., et al. Design, synthesis and pharmacological evaluation of N-benzyl linoleamide analogues from Tropaeolum tuberosum as NF-κB inhibitors and Nrf2 activators. ChemistrySelect 5(38), 11825-11836 (2020).