The vanilloids are compounds which possess a vanillyl group. They include

vanillyl alcohol Vanillyl alcohol is derived from vanillin. It is used to flavor food. See also * Anisyl alcohol * Guaiacol Guaiacol () is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing an methoxy functional group. G ...

vanillin Vanillin is an organic compound with the molecular formula . It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used ...

vanillic acid Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a dihydroxybenzoic acid derivative used as a flavoring agent. It is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Occurrence in natu ...

acetovanillon Apocynin, also known as acetovanillone, is a natural organic compound structurally related to vanillin. It has been isolated from a variety of plant sources and is being studied for its variety of pharmacological properties. History Apocynin w ...

vanillylmandelic acid Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines ( dopamine, epinephrine, and norepinephrine). It is produced via intermediary metabolite ...

homovanillic acid Homovanillic acid (HVA) is a major catecholamine metabolite that is produced by a consecutive action of monoamine oxidase and catechol-O-methyltransferase on dopamine. Homovanillic acid is used as a reagent to detect oxidative enzymes, and is ass ...

capsaicin Capsaicin (8-methyl-''N''-vanillyl-6-nonenamide) ( or ) is an active component of chili peppers, which are plants belonging to the genus ''Capsicum''. It is a chemical irritant for mammals, including humans, and produces a sensation of burning ...

, 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 Ion channels are pore-forming membrane proteins that allow ions to pass through the channel pore. Their functions include establishing a resting membrane potential, shaping action potentials and other electrical signals by gating the flow of io ...

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 Anandamide (ANA), also known as ''N''-arachidonoylethanolamine (AEA), is a fatty acid neurotransmitter. Anandamide was the first endocannabinoid to be discovered: it participates in the body's endocannabinoid system by binding to cannabinoid rec ...

20-Hydroxyeicosatetraenoic_acid 20-Hydroxyeicosatetraenoic acid, also known as 20-HETE or 20-hydroxy-5''Z'',8''Z'',11''Z'',14''Z''-eicosatetraenoic acid, is an eicosanoid metabolite of arachidonic acid that has a wide range of effects on the vascular system including the regula ...

(20-HETE) ,

N-Arachidonoyl_dopamine ''N''-Arachidonoyl dopamine (NADA) is an endocannabinoid that acts as an agonist of the CB1 receptor and the transient receptor potential V1 (TRPV1) ion channel. NADA was first described as a putative endocannabinoid (agonist for the CB1 recep ...

(NADA) and N-oleoyl-dopamine. : Outside the food industry vanilloids such as

nonivamide Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthe ...

are used commercially in

pepper spray Pepper spray, oleoresin capsicum spray, OC spray, capsaicin spray, or capsicum spray is a lachrymatory agent (a compound that irritates the eyes to cause a burning sensation, pain, and temporary blindness) used in policing, riot control, cr ...

formulations. Other vanilloids which act at TRPV1 include

resiniferatoxin Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge (''Euphorbia resinifera''), a cactus-like plant commonly found in Morocco, and in '' Euphorbia poissonii'' found in northern Nigeria.

and olvanil.

References

Literature

* {{Dead link, date=July 2018 , bot=InternetArchiveBot , fix-attempted=yes Phenols Phenol ethers