Homocapsaicin is a capsaicinoid and analog and
congener of
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 burnin ...
in
chili pepper
Chili peppers (also chile, chile pepper, chilli pepper, or chilli), from Nahuatl '' chīlli'' (), are varieties of the berry-fruit of plants from the genus ''Capsicum'', which are members of the nightshade family Solanaceae, cultivated for ...
s (''
Capsicum
''Capsicum'' () is a genus of flowering plants in the nightshade family Solanaceae, native to the Americas, cultivated worldwide for their chili pepper or bell pepper fruit.
Etymology and names
The generic name may come from Latin , me ...
''). Like capsaicin it is an
irritant. Homocapsaicin accounts for about 1% of the total capsaicinoids mixture and has about half the pungency of capsaicin. Pure homocapsaicin is a
lipophilic
Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipo ...
colorless odorless crystalline to waxy compound. On the
Scoville scale
The Scoville scale is a measurement of the pungency (spiciness or "heat") of chili peppers, as recorded in Scoville heat units (SHU), based on the concentration of capsaicinoids, among which capsaicin is the predominant component.
The scale i ...
it has 8,600,000 SHU (''Scoville heat units'').
Homocapsaicin isolated from chili pepper has been found in two
isomeric forms, both with a carbon-carbon
double bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betwee ...
at the 6 position (numbered from the amide carbon) on the 10-carbon acyl chain. One isomer has an additional carbon, a methyl group, at the 8 position and the other has a methyl group at the 9 position. Homocapsaicin (6-ene-8-methyl) is the more abundant isomer. Homocapsaicin with the double bond at the 7 position has never been found in nature, though its structure is widely reported on the Internet and in the scientific literature. Details of this misidentification have been published.
See also
*
Dihydrocapsaicin
Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (''Capsicum''). Like capsaicin, it is an irritant. It accounts for about 22% of the total capsaicinoid mixture and has the same pungency as capsaicin. P ...
*
Nordihydrocapsaicin
Nordihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (''Capsicum'').
Properties
Like capsaicin, it is an irritant. Nordihydrocapsaicin accounts for about 7% of the total capsaicinoids mixture and has ...
*
Homodihydrocapsaicin
*
Scoville scale
The Scoville scale is a measurement of the pungency (spiciness or "heat") of chili peppers, as recorded in Scoville heat units (SHU), based on the concentration of capsaicinoids, among which capsaicin is the predominant component.
The scale i ...
*
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, ...
*
Spice
A spice is a seed, fruit, root, bark, or other plant substance primarily used for flavoring or coloring food. Spices are distinguished from herbs, which are the leaves, flowers, or stems of plants used for flavoring or as a garnish. Spice ...
References
External links
Molecule of the Month
{{Transient receptor potential channel modulators
Phenols
Capsaicinoids
Phenol ethers