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 ...

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.

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{{Transient receptor potential channel modulators Phenols Capsaicinoids Phenol ethers

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