Homocapsaicin

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Homocapsaicin
Homocapsaicin.svg
Identifiers
CAS number 71240-51-2 N
PubChem 11674147
ChemSpider 9848876 YesY
Jmol-3D images Image 1
Properties
Molecular formula C19H29NO3
Molar mass 319.43 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
Homocapsaicin
Heat Above Peak (SR: 8,600,000)

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 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 it’s structure is widely reported on the internet and, unfortunately, even in the scientific literature. Details of the misidentification have been published.[1] (Note: the structure to the right is incorrect and has not yet been edited.)

See also[edit]

External links[edit]

  • ^ Thompson, R.Q. “Homocapsaicin: nomenclature, indexing, and identification” Flavour and Fragrance Journal 2007, 22, 243-248.