High-purity Capsaicin Analytical Standard

By: Michael Jeitziner, Market Segment Manager Analytical Reagents & Standards, Analytix 2012 Volume 5

Capsaicin is the primary active component of spicy chili peppers, the fruits of plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin is used as a food additive in various spicy cuisines, for therapeutic purposes to treat a number of peripheral painful conditions, as a pesticide, in pepper sprays, and as an ingredient in cosmetics1, 2.

Capsaicin (trans-8-methyl-N-vanillyl-6-nonenamide) is a crystalline, lipophilic, colorless and odorless alkaloid with the molecular formula C18H27NO3. Capsaicin displays cis/trans isomerism (see Figure 1). Naturally occuring capsaicin is always found in the trans form3.

Figure 1. The structure of E- and Z-Capsaicin

Therefore the Z-Capsaicin (cis form) can only be found in synthetically produced capsaicin, which should not be confused with synthetic capsaicin (Nonivamide) (see Figure 2).

Figure 2. 1H-NMR spectra of synthetically produced E-Capsaicin contaminated with Z-Capsaicin, Source: Syndeco GmbH, Switzerland


Pure Capsaicin isolated from Capsicum peppers usually contains impurities of other capsaicinoids, such as dihydrocapsaicin and nordihydrocapsaicin. Sigma-Aldrich has been able to produce and offer a superior quality of pure E-Capsaicin, with a guaranteed assay of ≥.99.0% by HPLC (Cat. No. 12084).

Related Information
A comprehensive list of our product line can be found at sigma-aldrich.com/medicinalplants
 

References

  • Pesticide Products. Pest-Bank [CD-ROM] 2007.
  • Johnson Jr. Int. J. Toxicol. 2007, 26 (Suppl. 1), 3–106.
  • De Lourdes Reyes-Escogido, Maria, et al. Molecules 2011, 16, 1253–1270; doi:10.3390/molecules16021253.

 

 

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