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.
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.
Last updated 31 January 2015.
(c) 1999-2016 Mike Whittemore
All graphics (c) 1999-2016 Mike Whittemore
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