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Overview of Major Capsaicinoids, Page 3

Introduction
Capsaicin
Dihydrocapsaicin
The Difference Between Capsaicin and DHC
Cis/Trans Isomerism in Capsaicin

Previous (Capsaicin)
Dihydrocapsaicin
The Dihydrocapsaicin Molecule
The Dihydrocapsaicin Molecule

Common name: Dihydrocapsaicin
Semi-systematic names: N-vanillyl-8-methyl-nonanamide; vanillylamide of 8-methylnonanoic acid
Systematic name: N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamide
Molecular formula: C18H29NO3
Molecular weight: 307.44

Detection Threshold: 25.97 ± 2.32 million SHU (Ref 9, 903). This is equivalent to a 0.0385 ppm solution of dihydrocapsaicin.

Pungency Threshold: 16.30 ± 1.52 million SHU (Ref 9, 904). This is equivalent to a 0.061 ppm solution of dihydrocapsaicin. Other studies have determined different pungency thresholds for dihydrocapsaicin; reported values range from 6.1 million to 16.1 million SHU (Ref 9, 902)

Type of pungency: Krajewska and Powers' study (Ref 9), showed that, in very dilute solution, dihydrocapsaicin had a pungency profile like that of capsaicin: a "sharp and stinging bite" located "in the mid-mouth and mid-palate as well as the throat and the back of the tongue" that developed quickly and was long-lived (Ref 9, 904).

Major molecular features that determine chemical behavior:
As capsaicin, except for the absence of the carbon-carbon double bond in the long hydrocarbon portion of the molecule.

Next (The Difference Between Capsaicin and DHC)

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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