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.
Chemistry
Vanillyl alcohol can be produced by reducing vanillin with sodium borohydride under basic conditions, then quenching using a strong acid such as hydrochloric acid ...
,
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 ethanolic extract of the vanilla bean. Synthetic vanillin ...
,
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 n ...
,
acetovanillon,
vanillylmandelic acid,
homovanillic acid,
capsaicin
Capsaicin (8-methyl-''N''-vanillyl-6-nonenamide) (, rarely ) is an active component of chili peppers, which are plants belonging to the genus ''Capsicum''. It is a potent Irritation, irritant for Mammal, mammals, including humans, and produces ...
, 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 (electrophysiol ...
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 referred to as ''N''-arachidonoylethanolamine (AEA) is a fatty acid neurotransmitter belonging to the fatty acid derivative group known as N-acylethanolamine (NAE). Anandamide takes its name from the Sanskrit word ''ananda ...
,
20-hydroxyeicosatetraenoic acid (20-HETE),
(NADA) and N-oleoyl-dopamine ().
[ ]
Fatty acid amide hydrolase
Fatty-acid amide hydrolase 1 (FAAH) is a member of the serine hydrolase family of enzymes. It was first shown to break down anandamide (AEA), an ''N''-acylethanolamine (NAE) in 1993. In humans, it is encoded by the gene ''FAAH''.;
Function
...
(FAAH), is a crucial
enzyme
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
for endovanilloid, and the
''N''-acylethanolamines (NAEs),
catabolism
Catabolism () is the set of metabolic pathways that breaks down molecules into smaller units that are either oxidized to release energy or used in other anabolic reactions. Catabolism breaks down large molecules (such as polysaccharides, lipid ...
at TRPV1, and other
cannabinoid receptors.
:
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 sy ...
are used commercially in
pepper spray
Pepper spray, oleoresin capsicum spray, OC spray, capsaicin spray, mace, or capsicum spray is a Tear gas, lachrymator (tear gas) product containing as its active ingredient the chemical compound capsaicin, which irritates the eyes with burning ...
formulations.
Other vanilloids which act at TRPV1 include
resiniferatoxin and
olvanil.
References
Literature
* {{Dead link, date=July 2018 , bot=InternetArchiveBot , fix-attempted=yes
Phenols
Phenol ethers