A terpene alkaloid with diverse biological activities
Related Products
Alternative(s)
92350Capsaicin
Labeled Version(s)
34695(E/Z)-Capsaicin-d3
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Capsaicin (technical grade)

Item No. 10010743

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
CAS Number
404-86-4
Molecular Formula
C18H27NO3
Formula Weight
305.4
Purity
≥60% (mixture of capsaicinoids)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 30 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.1 mg/ml
λmax
230, 281 nm
SMILES
COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
InChi Code
InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChi Key
YKPUWZUDDOIDPM-SOFGYWHQSA-N
Origin
Plant/Capsicum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 mg

    $36

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    1 g

    $68

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    5 g

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    10 g

    $436

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    Product Description

    Capsaicin is a terpene alkaloid that has been found in Capsicum and has diverse biological activities.1,2,3,4 It induces inward currents in HEK293 cells expressing rat transient receptor potential vanilloid 1 (TRPV1; EC50 = 0.64 µM at neutral pH), an effect that can be blocked by the TRPV1 inhibitor A-425619.1 Capsaicin (10 and 50 µM) decreases LPS-induced prostaglandin E2 (PGE2; Item No. 14010) production, as well as reduces LPS- and IFN-induced nitric oxide (NO) release in isolated mouse peritoneal macrophages.2 Capsaicin induces substance P (Item No. 24035) release in rat spinal cord slices with an EC50 value of 2.3 µM.3 It reduces acetylcholine- or phenylquinone-induced writhing (ED50s = 1.33 and 1.38 mg/kg, respectively, s.c.) but has no effect on the latency to paw withdrawal in the hot plate test in mice (ED50 = >20 mg/kg, s.c.).4 Formulations containing capsaicin have been used in the treatment of nerve pain associated with shingles.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Neelands, T.R., Jarvis, M.F., Han, P., et al. Acidification of rat TRPVI alters the kinetics of capsaicin responses. Mol. Pain 1, 28 (2005).

    2. Kim, C.-S., Kawada, T., Kim, B.-S., et al. Capsaicin exhibits anti-inflammatory property by inhibiting IkB-a degradation in LPS-stimulated peritoneal macrophages. Cell. Signal. 15(3), 299-306 (2003).

    3. Marvizón, J.C.G., Wang, X., Matsuka, Y., et al. Relationship between capsaicin-evoked substance P release and neurokinin 1 receptor internalization in the rat spinal cord. Neuroscience 118(2), 535-545 (2003).

    4. Hayes, A.G., Skingle, M., and Tyers, M.B. Effects of single doses of capsaicin on nociceptive thresholds in the rodent. Neuropharmacology 20(5), 505-511 (1981).