Issue 39, 2021

Boron-containing capsaicinoids


This study reports on the preparation of eight new boron-containing capsaicinoids bearing long aliphatic chains, as an expansion of our previous studies to include tertiary amide derivatives into our substrate scope. Our boron-moiety, a pinacolboronate ester (Bpin) fragment, has been incorporated in two locations: as an aryl substituent of the capsaicinoid produced by the reductive amination of veratraldehyde, or at the terminal end of an aliphatic substituent using an iridium catalyzed hydroboration reaction. We report that most compounds in our series show moderate antimicrobial and cytotoxic activity, surpassing activities noted in our previous study.

Graphical abstract: Boron-containing capsaicinoids

Supplementary files

Article information

Article type
25 Jun 2021
06 Jul 2021
First published
23 Jul 2021
This article is Open Access
Creative Commons BY license

RSC Adv., 2021,11, 24282-24291

Boron-containing capsaicinoids

J. A. Melanson, M. F. Landry, M. Lanteigne, K. McQuillan, H. Correa, R. G. Kerr and S. A. Westcott, RSC Adv., 2021, 11, 24282 DOI: 10.1039/D1RA04943G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity