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
CAS Number	71240-51-2 N
ChemSpider	9848876 Y
Jmol 3D model	Interactive image
PubChem	11674147
InChI 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+ Y Key: MLJGZARGNROKAC-VQHVLOKHSA-N Y 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
SMILES O=C(NCC1=CC(OC)=C(O)C=C1)CCCC/C=C/C(CC)C
Properties
Chemical formula	C19H29NO3
Molar mass	319.43 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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 its structure is widely reported on the Internet and, unfortunately, even in the scientific literature. Details of the misidentification have been published. (Note: the structure to the right is incorrect and has not yet been edited.)

See also

• Capsaicin
• Dihydrocapsaicin
• Nordihydrocapsaicin
• Homodihydrocapsaicin
• Scoville scale
• Pepper spray
• Spice

External links

• Molecule of the Month
• Hotness scale of different capsaicinoids and pepper varieties