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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Infobox references
Homocapsaicin
HeatAbove peak
Scoville scale8,600,000[1] 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[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]

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. ↑ Thompson, Robert Q (2007). "Homocapsaicin: Nomenclature, indexing and identification". Flavour and Fragrance Journal. 22 (4): 243–248. doi:10.1002/ffj.1814.
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