Main : Science : Chemistry : Minor Capsaicinoids

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Overview of Minor Capsaicinoids, Page 3

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Homocapsaicin II
Homodihydrocapsaicin II
Vanillylamide of octanoic acid
Vanillylamide of nonanoic acid
Vanillylamide of decanoic acid

Vanillylamide of nonanoic acid
Vanillylamide of nonanoic acid
Vanillylamide of nonanoic acid

Common name: None
Semi-systematic names: N-vanillyl-nonanamide; vanillylamide of nonanoic acid
Systematic name: N-(4-hydroxy-3-methoxybenzyl)-nonanamide
Molecular formula: C17H27NO3
Molecular weight: 293.41

Detection Threshold: 18.65 ± 2.48 million SHU (Ref 9, 903).

Pungency Threshold: 9.32 ± 1.21 million SHU (Ref 9, 904). Other studies have determined different pungency thresholds for the vanillylamide of nonanoic acid; reported values range from 8.8 million to 9.3 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), the vanillylamide of nonanoic acid, in a very dilute solution, was noted as producing a "mellow, warming effect" and "biting sensation" which "developed immediately" and "receded rapidly" "in [the] front of the mouth and palate" (Ref 9, 904).

Vanillylamide of decanoic acid
Vanillylamide of decanoic acid
Vanillylamide of decanoic acid

Common name: None
Semi-systematic names: N-vanillyldecanamide; Vanillylamide of decanoic acid
Systematic name: N-(4-hydroxy-3-methoxybenzyl)-decanamide
Molecular formula: C18H29NO3
Molecular weight: 307.43

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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