Vanilloid
Chemical compounds containing a vanillyl group
The vanilloids are compounds which possess a vanillyl group. They include vanillyl alcohol, vanillin, vanillic acid, acetovanillone, vanillylmandelic acid, homovanillic acid, capsaicin, etc. Isomers are the isovanilloids.
A number of vanilloids, most notably capsaicin, bind to the transient receptor potential vanilloid type 1 (TRPV1) receptor, an ion channel which naturally responds to noxious stimuli such as high temperatures and acidic pH. This action is responsible for the burning sensation experienced after eating spicy peppers. Endogenously generated chemicals that trigger the TRPV1 channel of the vanilloid class are referred to as endovanilloids including anandamide, 20-hydroxyeicosatetraenoic acid (20-HETE), N-arachidonoyl dopamine (NADA) and N-oleoyl-dopamine (CID 5282106 from PubChem).
Fatty acid amide hydrolase (FAAH), is a crucial enzyme for endovanilloid, and the N-acylethanolamines (NAEs), catabolism at TRPV1, and other cannabinoid receptors.
Outside the food industry vanilloids such as nonivamide are used commercially in pepper spray formulations.
Other vanilloids which act at TRPV1 include resiniferatoxin and olvanil.
01Literature
- Lee, Jeewoo; Uk Kang, Sang; Yeon Kim, Su; Eun Kim, Sung; Joon Jo, Yeong; Kim, Sunghoon (2001). "Vanilloid and Isovanilloid Analogues as Inhibitors of Methionyl-tRNA and Isoleucyl-tRNA Synthetases" (PDF). Bioorganic & Medicinal Chemistry Letters. 11 (8): 965, 968. doi:10.1016/S0960-894X(01)00096-8. PMID 11327601.
Sources and credits
This article is adapted from the Wikipedia article “Vanilloid”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Vanillin.svg by Calvero., Public domain
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