Vanilloids

Short description: 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.

	Structure of Vanillin	Structure of vanillic acid	Structure of acetovanillon	Structure of vanillylamine
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.^[1] 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^[2] including anandamide, 20-Hydroxyeicosatetraenoic acid(20-HETE)^[3],N-Arachidonoyl dopamine (NADA) and N-oleoyl-dopamineCID 5282106 from PubChem.^[4]


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.

^[5]

References

↑ Pingle, SC; Matta, JA; Ahern, GP (2007). Capsaicin receptor: TRPV1 a promiscuous TRP channel. Handbook of Experimental Pharmacology. 179. pp. 155–171. doi:10.1007/978-3-540-34891-7_9. ISBN 978-3-540-34889-4.
↑ Van Der Stelt M, Di Marzo V (2004). "Endovanilloids. Putative endogenous ligands of transient receptor potential vanilloid 1 channels.". Eur J Biochem 271 (10): 1827–34. doi:10.1111/j.1432-1033.2004.04081.x. PMID 15128293.
↑ 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 179 (7): 1450–1469. doi:10.1111/bph.15726. PMID 34755897. https://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=34755897.
↑ 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 143 (2): 251–6. doi:10.1038/sj.bjp.0705924. PMID 15289293.
↑ Carlson, Neil R.; Birkett, Melissa A. (2017). Physiology of Behavior (12 ed.). Pearson. p. 212. ISBN 9780134320823.

Literature

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[1] Pingle, SC; Matta, JA; Ahern, GP (2007). Capsaicin receptor: TRPV1 a promiscuous TRP channel. Handbook of Experimental Pharmacology. 179. pp. 155–171. doi:10.1007/978-3-540-34891-7_9. ISBN 978-3-540-34889-4.

[pmid15128293-2] Van Der Stelt M, Di Marzo V (2004). "Endovanilloids. Putative endogenous ligands of transient receptor potential vanilloid 1 channels.". Eur J Biochem 271 (10): 1827–34. doi:10.1111/j.1432-1033.2004.04081.x. PMID 15128293.

[pmid34755897-3] 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 179 (7): 1450–1469. doi:10.1111/bph.15726. PMID 34755897. https://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=34755897.

[pmid15289293-4] 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 143 (2): 251–6. doi:10.1038/sj.bjp.0705924. PMID 15289293.

[5] Carlson, Neil R.; Birkett, Melissa A. (2017). Physiology of Behavior (12 ed.). Pearson. p. 212. ISBN 9780134320823.