An amide alkaloid with diverse biological activities
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Pellitorine

Item No. 11662

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,4E)-N-(2-methylpropyl)-2,4-decadienamide
CAS Number
18836-52-7
Molecular Formula
C14H25NO
Formula Weight
223.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
λmax
259 nm
SMILES
O=C(/C=C/C=C/CCCCC)NCC(C)C
InChi Code
InChI=1S/C14H25NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h8-11,13H,4-7,12H2,1-3H3,(H,15,16)/b9-8+,11-10+
InChi Key
MAGQQZHFHJDIRE-BNFZFUHLSA-N
Origin
Plant/Piper longum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $32

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    5 mg

    $96

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    10 mg

    $160

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    25 mg

    $319

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    Product Description

    Pellitorine is an amide alkaloid that has been found in P. nigrum and has diverse biological activities.1,2,3,4 Pellitorine is cytotoxic to HL-60 leukemia and MCF-7 breast cancer cells (IC50s = 13 and 1.8 µg/ml, respectively).3 It inhibits production of TNF-α, IL-1α, and IL-1β and phosphorylation of ERK1/2 induced by high mobility group protein B1 (HMGB1) in human umbilical vein endothelial cells (HUVECs) when used at concentrations of 10 and 20 µM.4 Pellitorine (9 µg/animal, i.v.) prolongs survival time in a mouse model of sepsis induced by HMGB1.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wei, K., Li, W., Koike, K., et al. New amide alkaloids from the roots of Piper nigrum. J. Nat. Prod. 67(6), 1005-1009 (2004).

    2. Park, I.K., Lee, S.G., Shin, S.C., et al. Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species. J. Agric. Food Chem. 50(7), 1866-1870 (2002).

    3. Ee, G.C., Lim, C.M., Rahmani, M., et al. Pellitorine, a potential anti-cancer lead compound against HL6 and MCT-7 cell lines and microbial transformation of piperine from Piper Nigrum. Molecules 15(4), 2398-2404 (2010).

    4. Ku, S.K., Lee, I.C., Kim, J.A., et al. Anti-septic effects of pellitorine in HMGB1-induced inflammatory responses in vitro and in vivo. Inflammation 37(2), 338-348 (2014).