Homocapsaicin

Homocapsaicin
Names
IUPAC name
(6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyldec-6-enamide
Other names
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
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C19H29NO3/c1-4-15(2)9-7-5-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h7,9,11-13,15,21H,4-6,8,10,14H2,1-3H3,(H,20,22)/b9-7+ checkY
    Key: MLJGZARGNROKAC-VQHVLOKHSA-N checkY
  • InChI=1/C19H29NO3/c1-4-15(2)9-7-5-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h7,9,11-13,15,21H,4-6,8,10,14H2,1-3H3,(H,20,22)/b9-7+
    Key: MLJGZARGNROKAC-VQHVLOKHBL
  • O=C(NCC1=CC(OC)=C(O)C=C1)CCCC/C=C/C(CC)C
Properties
C19H29NO3
Molar mass 319.43 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Homocapsaicin
HeatAbove peak
Scoville scale8,600,000 SHU

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 cis 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

References

  1. 1 2 Govindarajan, 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. PMID 2039598.
  2. ↑ Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin". J. Chem. Soc. C: 442. doi:10.1039/j39680000442.
  3. 1 2 Thompson, Robert Q (2007). "Homocapsaicin: Nomenclature, indexing and identification". Flavour and Fragrance Journal. 22 (4): 243–248. doi:10.1002/ffj.1814. hdl:10348/1677.