A terpene alkaloid with diverse biological activities
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Dihydrocapsaicin

Item No. 92355

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-nonanamide
CAS Number
19408-84-5
Synonyms
  • DHC
Molecular Formula
C18H29NO3
Formula Weight
307.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 33 mg/mlEthanol: 100 mg/mlPBS (pH 7.2): 0.1 mg/ml
λmax
230, 281 nm
SMILES
COc1cc(CNC(=O)CCCCCCC(C)C)ccc1O
InChi Code
InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)
InChi Key
XJQPQKLURWNAAH-UHFFFAOYSA-N
Origin
Semisynthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $36

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    10 mg

    $68

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    50 mg

    $253

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    100 mg

    $436

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    Product Description

    Dihydrocapsaicin is a terpene alkaloid that has been found in Capsicum and has diverse biological activities.1,2,3 It is active against E. faecalis, B. subtilis, S. aureus, P. aeruginosa, K. pneumoniae, E. coli, and C. albicans (MICs = 0.6-10 µg/ml).1 Dihydrocapsaicin scavenges DPPH (Item No. 14805) and ABTS (Item No. 27317) radicals in cell-free assays. It increases LC3-II, a marker of autophagy, and catalase levels and reduces reactive oxygen species (ROS) production in normal WI38 lung fibroblasts and H1299, but not A549 or H460, lung cancer cells when used at a concentration of 200 µM.2 Dihydrocapsaicin is an agonist of transient receptor potential vanilloid 1 (TRPV1) and inhibits NETosis induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in isolated human neutrophils.4,5 It induces cortical and systemic hypothermia and reduces infarct volume in a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO) when administered at a dose of 0.5 mg/kg, i.p.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nascimento, P.L.A., Nascimento, T.C.E.S., Ramos, N.S.M., et al. Quantification, antioxidant and antimicrobial activity of phenolics isolated from different extracts of Capsicum frutescens (pimenta malagueta). Molecules 19(4), 5434-5447 (2014).

    2. Choi, C.-H., Jung, Y.-K., and Oh, S.-H. Selective induction of catalase-mediated autophagy by dihydrocapsaicin in lung cell lines. Free Radic. Biol. Med. 49(2), 245-257 (2010).

    3. Wu, D., Shi, J., Elmadhoun, O., et al. Dihydrocapsaicin (DHC) enhances the hypothermia-induced neuroprotection following ischemic stroke via PI3K/Akt regulation in rat. Brain Res. 1671, 18-25 (2017).

    4. Feketa, V.V., Balasubramanian, A., Flores, C.M., et al. Shivering and tachycardic responses to external cooling in mice are substantially suppressed by TRPV1 activation but not by TRPM8 inhibition. Am. J. Physiol. Regul. Integr. Comp. Physiol. 305(9), R1040-R1050 (2013).

    5. Sondo, E., Bertelli, R., Pesce, E., et al. High-content screening identifies vanilloids as a novel class of inhibitors of NET formation. Front. Immunol. 10, 963 (2019).