Main : Science : Chemistry : Minor Capsaicinoids

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Overview of Minor Capsaicinoids

Previous (Cis/Trans Isomerism in Capsaicin)
Homocapsaicin
Homocapsaicin II
Homodihydrocapsaicin
Homodihydrocapsaicin II
Nordihydrocapsaicin
Vanillylamide of octanoic acid
Vanillylamide of nonanoic acid
Vanillylamide of decanoic acid

Homocapsaicin
The Homocapsaicin Molecule
The Homocapsaicin Molecule

Common name: Homocapsaicin
Semi-systematic names: N-vanillyl-9-methyldec-7-(E)-enamide; trans-N-vanillyl-9-methyldec-7-enamide; vanillylamide of 9-methyldec-trans-7-enoic acid
Systematic name: N-(4-hydroxy-3-methoxybenzyl)-9-methyldec-trans-7- enamide
Molecular formula: C19H29NO3
Molecular weight: 319.45

Pungency Threshold: 8.6 million SHU (Ref 7, 461). Other studies have determined different pungency thresholds for homocapsaicin; reported values range from 6.9 million to 13.1 million SHU (Ref 9, 902).
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Homocapsaicin II
The Homocapsaicin II Molecule
The Homocapsaicin II Molecule

Common name: Homocapsaicin II
Semi-systematic names: N-vanillyl-8-methyldec-trans-6-enamide; vanillylamide of 8-methyldec-trans-6-enoic acid
Systematic name: N-(4-hydroxy-3-methoxybenzyl)-8-methyldec-trans-6-enamide
Molecular formula: C19H29NO3
Molecular weight: 319.45
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Homodihydrocapsaicin
The Homodihydrocapsaicin Molecule
The Homodihydrocapsaicin Molecule

Common name: Homodihydrocapsaicin
Semi-systematic names: N-vanillyl-9-methyldecanamide; vanillylamide of 9-methyldecanoic acid
Systematic name: N-(4-hydroxy-3-methoxybenzyl)-9-methyldecanamide
Molecular formula: C19H31NO3
Molecular weight: 321.46

Detection Threshold: 24.16 ± 4.18 million SHU (Ref 9, 903).

Pungency Threshold: 14.04 ± 1.01 million SHU (Ref 9, 904). Other studies have determined different pungency thresholds for homodihydrocapsaicin; reported values range from 8.1 million to 8.6 million SHU (Ref 9, 902 and Ref 7, 461)

Type of pungency: In a detailed study performed by Anna Krajewska and John Powers (Ref 9), homodihydrocapsaicin, in a very dilute solution, was noted as producing a "very irritating, harsh, and very sharp" "numbing burn" located in the throat and the back of the tongue and palate that developed slowly and "was prolonged and difficult to rinse out" (Ref 9, 904).
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Next (Overview of Minor Capsaicinoids, page 2)

All of the chemical structures and reaction mechanism diagrams used in this section are my own creations. None of the chemical structures that I've seen on any other Chile Head sites show unshared electrons, nor do they properly depict the unsaturation in the capsaicin molecule, both of which are major determinants of the chemical behavior of capsaicin. Due to the use of a really cheesy red-gold Chrome effect, all of my technical artwork is readily identifiable (and hopefully too ugly to steal). If you see someone else using my artwork without giving proper credits, please 1) give them a boot in the rear via email, and/or 2) let me know about it so I can do the same.


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