Vanilloids

The vanilloids are compounds which possess a vanillyl group. They include vanillyl alcohol, vanillin, vanillic acid, acetovanillon, vanillylmandelic acid, homovanillic acid, capsaicin, etc. Isomers are the isovanilloids.


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 * Vanillylalkohol.svg || Vanillin2.svg || Vanillinsäure.svg || Acetovanillone.svg
 * vanillyl alcohol || vanillin || vanillic acid || acetovanillon
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 * vanillyl alcohol || vanillin || vanillic acid || acetovanillon
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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.

Outside of the food industry, vanilloids such as nonivamide are used commercially in pepper spray formulations.

Other vanilloids which act at TRPV1 include resiniferatoxin and olvanil.

Literature

 * Jeewoo Lee, Sang Uk Kang, Su Yeon Kim, Sung Eun Kim, Yeong Joon Jo, Sunghoon Kim: Vanilloid and Isovanilloid Analogues as Inhibitors of Methionyl-tRNA and Isoleucyl-tRNA Synthetases, Bioorganic & Medicinal Chemistry Letters, 2001, 11 (8), pp. 965–968; ; PMID 11327601; PDF.

Vanilloide