Homocapsaicin is a capsaicinoid and analog and
congener of
capsaicin in
chili peppers (''
Capsicum''). 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 colorless odorless crystalline to waxy compound. On the
Scoville scale it has 8,600,000 SHU (''Scoville heat units'').
Homocapsaicin isolated from chili pepper has been found in two
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
ic forms, both with a carbon-carbon
double bond 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
*
Nordihydrocapsaicin
*
Homodihydrocapsaicin
*
Scoville scale
*
Pepper spray
*
Spice
References
External links
Molecule of the Month
{{Transient receptor potential channel modulators
Phenols
Capsaicinoids
Phenol ethers