Capsaicin is the primary active component of the heat and pain-eliciting lipid soluble fraction of the Capsicum pepper.1 Capsaicin is found in natural hot pepper extracts along with a number of impurities, including dihydrocapsaicin and several lesser impurities. Separation by HPLC is required in order to obtain pure dihydrocapsaicin.2 Dihydrocapsaicin represents about 10% of the compound present in commercial preparations purporting to be pure capsaicin. VR1 (vanilloid receptor 1) is a heat activated calcium ion channel which functions as a part of the normal nociceptive pain pathway. Capsaicin elicits a sensation of burning pain by activation of VR1 on small, non-myelinated polymodal C-type nociceptive nerve fibers.3 The potency of dihydrocapsaicin at VR1 appears equivalent to capsaicin.
1
Gannett, P.M., Nagel, D.L., Reilly, P.J., et al. The capsaicinoids: Their separation, synthesis, and mutagenicity. J Org Chem53(5)1064-1071(1988).
2
Hoffman, P.G., Lego, M.C., and Galetto, W.G. Separation and quantitation of red pepper major heat principles by reverse-phase high-pressure liquid chromatography. J Agric Food Chem31(6)1326-1330(1983).
3
Caterina, M.J., Schumacher, M.A., Tominaga, M., et al. The capsaicin receptor: A heat-activated ion channel in the pain pathway. Nature389816-824(1997).
Room temperature
in continental US; may vary elsewhere
SMILES
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COc1cc(CNC(=O)CCCCCCC(C)C)ccc1O
Background Reading
Caterina, M.J., Schumacher, M.A., Tominaga, M., et al. The capsaicin receptor: A heat-activated ion channel in the pain pathway. Nature389816-824(1997).
Gannett, P.M., Nagel, D.L., Reilly, P.J., et al. The capsaicinoids: Their separation, synthesis, and mutagenicity. J Org Chem53(5)1064-1071(1988).
Hoffman, P.G., Lego, M.C., and Galetto, W.G. Separation and quantitation of red pepper major heat principles by reverse-phase high-pressure liquid chromatography. J Agric Food Chem31(6)1326-1330(1983).
Dihydrocapsaicin is available in the following screening
library: