Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2011 Jan 28;16(2):1253-70.
doi: 10.3390/molecules16021253.

Chemical and pharmacological aspects of capsaicin

Maria de Lourdes Reyes-Escogido  1 , Edith G Gonzalez-Mondragon, Erika Vazquez-Tzompantzi
Affiliations
Review

Chemical and pharmacological aspects of capsaicin

Maria de Lourdes Reyes-Escogido et al. Molecules. .

Abstract

Capsaicin is a unique alkaloid found primarily in the fruit of the Capsicum genus and is what provides its spicy flavor. Generally extracted directly from fruit, high demand has driven the use of established methods to increase production through extraction and characterization. Over time these methods have improved, usually be applying existing techniques in conjunction. An increasingly wide range of potential applications has increased interest in capsaicin. Especially compelling are the promising results of medical studies showing possible beneficial effects in many diseases. Capsaicin's pungency has limited its use in clinical trials to support its biological activity. Characterization and extraction/ synthesis of non-pungent analogues is in progress. A review is made of capsaicin research focusing mainly on its production, synthesis, characterization and pharmacology, including some of its main potential clinical uses in humans.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Regions of the molecule of capsaicin. A (aromatic ring); B (amide bond); and C (hydrophobic side chain).
Figure 2
Figure 2
Chemical structure of different capsaicinoids and their analogues. R Capsaicinoids and analogues.
Figure 3
Figure 3
Synthesis of capsaicin analogues using different amines and donors as substrates.
Figure 4
Figure 4
Structures of capsaicin and capsiate. Capsiate has an ester bond, whereas capsaicin has an amide bond at the equivalent position.
See this image and copyright information in PMC

References

    1. Bernal M.A., Calderon A.A., Pedreno M.A., Muñoz R., Ros Barceló A., Merino de Caceres F. Capsaicin oxidation by peroxidase from Capsicum annuum (variety Annuum) fruits. J. Agric. Food Chem. 1993;41:1041–1044. doi: 10.1021/jf00031a004. - DOI
    1. Walpole C.S., Bevan S., Bloomfield G., Breckenridge R., James I.F., Ritchie T., Szallasi A., Winter J., Wrigglesworth R. Similarities and differences in the structure-activity relationships of capsaicin and resiniferatoxin analogues. J. Med. Chem. 1996;39:2939–2952. - PubMed
    1. Kobata K., Kawamura M., Toyoshima M., Tamura Y., Ogawa S., Watanabe T. Lipase-catalyzed synthesis of capsaicin analogs by amidation of vanillylamine with fatty acid derivatives. Biotechnol. Lett. 1998;20:451–454.
    1. Nelson E.K., Dawson L.E. The constitution of capsaicin, the pungent principle of Capsicum. III. J. Am. Chem. Soc. 1923;45:2179–2181.
    1. [accessed on 28 January 2011]. Available online: http://www.3dchem.com/molecules.asp?ID=105.

Publication types

LinkOut - more resources