Homocapsaicin is a capsaicinoid and analog and congener of

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 ...

chili pepper Chili peppers, also spelled chile or chilli ( ), are varieties of fruit#Berries, berry-fruit plants from the genus ''Capsicum'', which are members of the nightshade family Solanaceae, cultivated for their pungency. They are used as a spice to ...

s (''

Capsicum ''Capsicum'' () is a genus of flowering plants in the Solanum, nightshade family Solanaceae, native to the Americas, cultivated worldwide for their edible fruit, which are generally known as "peppers" or "capsicum". Chili peppers grow on five s ...

''). 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 language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...

colorless odorless crystalline to waxy compound. On the

Scoville scale The Scoville scale is a measurement of spiciness of chili peppers and other substances, recorded in Scoville heat units (SHU). It is based on the concentration of capsaicinoids, among which capsaicin is the predominant component. The 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 formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

ic 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 betw ...

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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Molecule of the Month
{{Transient receptor potential channel modulators Phenols Capsaicinoids Phenol ethers

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