Homocapsaicin II, N-Vanillyl-8-methyldec-6-(E)-enamide, trans-N-Vanillyl-8-methyldec-6-enamide, N-(4-Hydroxy-3-methoxybenzyl)-8-methyldec-trans-6-enamide, Vanillylamide of 8-methyldec-trans-6-enoic acid, HC
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[2] 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).[1] Homocapsaicin isolated from chili pepper has been found in two
isomeric 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.[3]
^
abGovindarajan, Sathyanarayana (1991). "Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences". Critical Reviews in Food Science and Nutrition. 29 (6): 435–474.
doi:
10.1080/10408399109527536.
PMID2039598.
^Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin". J. Chem. Soc. C: 442.
doi:
10.1039/j39680000442.
^Thompson, Robert Q (2007). "Homocapsaicin: Nomenclature, indexing and identification". Flavour and Fragrance Journal. 22 (4): 243–248.
doi:
10.1002/ffj.1814.