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Overview of Major Capsaicinoids, Page 2

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

Previous (Introduction)
Capsaicin
The Capsaicin Molecule
The Capsaicin Molecule

Common name: Capsaicin
Semi-systematic names: N-vanillyl-8-methyl-6-(E)-nonenamide; trans-N-vanillyl-8-methyl-6-nonenamide; vanillylamide of 8-methylnon-trans-6-enoic acid
Systematic name: N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-trans-6- enamide
CAS Number: 404-86-4
Molecular formula: C18H27NO3
Molecular weight: 305.42
Melting point: 65 oC (Ref 8, 1811)
Boiling point: 210-220 oC at 0.01 torr pressure (Ref 8, 1811)
UV maxima: 227 nm, 281 nm (Ref 8, 1811)
Solubility: freely soluble in ethanol, ether, benzene, chloroform; slightly soluble in carbon disulfide; insoluble in water (Ref 8, 1811)

Detection Threshold: 26.35 ± 2.98 million Scoville Heat Units (SHU) [=] mL/g (Ref 9, 903). The detection threshold is the lowest concentration of capsaicinoid (in SHU, or mL/g) at which a sample of standard sugar water containing a capsaicinoid can be differentiated by taste (organoleptic evaluation) from a blank sample of standard sugar water. As 1 SHU = 1 mL/g, this means that the subjects in the study, on average, were able to tell a solution containing 1 gram of capsaicin in 26.35 million mL of standard sugar water (about 7000 gallons) apart from plain sugar water by taste. If the density of water is taken to be 1 g/mL, this solution would be 0.000003795% by weight capsaicin.

Pungency Threshold: 16.35 ± 2.28 million SHU (Ref 9, 904). The pungency threshold is the lowest concentration of capsaicinoid in a standard sugar water solution (in SHU, or mL/g) at which a "distinct sensation of pungency" is noted during organoleptic evaluation. 16.35 million SHU is equivalent to 1 gram of capsaicinoid in about 4315 gallons of sugar water, or a 0.000006116% by weight solution of capsaicinoid. Other studies have determined different pungency thresholds for capsaicin; reported values range from 9.2 million to 17.0 million SHU (Ref 9, 902)

Huh?!? Since Merck lists capsaicin as being insoluble in water, just how, you may ask, are these sugar-and-fire water concoctions prepared for these tests? Especially at such ridiculously low concentrations, like a gram in a 5000 gallon zoo-sized aquarium! Good question! If you want to know the answer, read about serial dilution.

Type of pungency: In a detailed study performed by Anna Krajewska and John Powers (Ref 9), subjects noted that very dilute solutions of the various capsaicinoids produced different types of pungency. These differences were not noted using more concentrated solutions. Capsaicin, in a very dilute solution, was noted as producing 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:

Feature Name or Description Implication Learn More
C=C carbon-carbon double bond Subject to at least some reactions typical of alkenes; cis/trans isomerism Learn more about alkenes
R-NH-(C=O)-R' secondary amide Subject to reactions typical of secondary amides Learn more about amides
ring: C6H3 tri-substituted benzene ring Subject to at least some reactions typical of substituted benzene rings  
Ring-OH phenol Subject to at least some reactions typical of phenols Learn more about alcohols
R-O-R' ether Subject to at least some reactions typical of ethers Learn more about ethers

All Learn More links point to an *excellent* online chemistry tutorial at The University of Akron.


Next (Dihydrocapsaicin)

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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