Vanilloid

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title: "Vanilloid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["vanilloids", "phenols", "phenol-ethers"] description: "Chemical compounds containing a vanillyl group" topic_path: "general/vanilloids" source: "https://en.wikipedia.org/wiki/Vanilloid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compounds containing a vanillyl group ::

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.

:{| class="wikitable" style="text-align:center; font-size:90%" |- | [[File:Vanillylalkohol.svg|115px|Structure of vanillyl alcohol]] || [[File:Vanillin2.svg|120px|Structure of Vanillin]] || [[File:Vanillinsäure.svg|120px|Structure of vanillic acid]] || [[File:Acetovanillone.svg|120px|Structure of acetovanillon]] || [[File:Vanillylamine.svg|120px|Structure of vanillylamine]] || [[File:kapsaicyna.svg|300px|Structure of Capsaicin]] |- | vanillyl alcohol || vanillin || vanillic acid || acetovanillon || Vanillylamine || Capsaicin |}

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 vanilloids class are referred to as endovanilloids including anandamide, 20-hydroxyeicosatetraenoic acid (20-HETE), N-arachidonoyl dopamine (NADA) and N-oleoyl-dopamine ().

Fatty acid amide hydrolase (FAAH), is a crucial enzyme for endovanilloid, and the N-acylethanolamines (NAEs), catabolism at TRPV1, and other cannabinoid receptors.

:{| class="wikitable" style="text-align:center; font-size:90%" |- | [[File:Anandamide_skeletal.svg|115px|Structure of Anandamide]] |- | Anandamide |} 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.

References

Literature

References

1. (2007). "Capsaicin receptor: TRPV1 a promiscuous TRP channel".
2. Van Der Stelt M, Di Marzo V. (2004). "Endovanilloids. Putative endogenous ligands of transient receptor potential vanilloid 1 channels.". Eur J Biochem.
3. Hamers A, Primus CP, Whitear C, Kumar NA, Masucci M, Montalvo Moreira SA. (2022). "20-hydroxyeicosatetraenoic acid (20-HETE) is a pivotal endogenous ligand for TRPV1-mediated neurogenic inflammation in the skin.". Br J Pharmacol.
4. De Petrocellis L, Chu CJ, Moriello AS, Kellner JC, Walker JM, Di Marzo V. (2004). "Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels.". Br J Pharmacol.
5. (2016-08-01). "Endovanilloid control of pain modulation by the rostroventromedial medulla in an animal model of diabetic neuropathy". Neuropharmacology.
6. (2017). "Physiology of Behavior". Pearson.

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