Dihydrocapsaicin

Dihydrocapsaicin
Names
IUPAC name
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnonanamide
Other names
N-[(4-Hydroxy-3-methoxy-phenyl)methyl]-8-methyl-nonanamide, Dihydrocapsaicin, 6,7-Dihydrocapsaicin, 8-Methyl-N-vanillylnonanamide, Vanillylamide of 8-methylnonanoic acid, DHC, CCRIS 1589
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.115.366
RTECS number RA5998000
UNII
Properties
C18H29NO3
Molar mass 307.43 g/mol
Appearance White to off-white solid
Sparingly soluble
Hazards
Toxic (T)
R-phrases (outdated) R25, R36/37/38
S-phrases (outdated) S26, S36/37/39, S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Dihydrocapsaicin
Heat Above peak
Scoville scale 16,000,000[1] SHU
MS/MS spectra of standard dihydrocapsaicin (A) and from sample extract (B). Sample B confirms the compound was found in prehispanic pottery from Mexico. See here for details doi:10.1371/journal.pone.0079013.g005

Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin, it is an irritant. Dihydrocapsaicin accounts for about 22% of the total capsaicinoid mixture[2] and has the same pungency as capsaicin.[1] Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is soluble in dimethyl sulfoxide and 100% ethanol.

See also

References

  1. 1 2 Govindarajan, Sathyanarayana (1991). "Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences". Critical Reviews in Food Science and Nutrition. 29 (6): 435–474.
  2. ↑ Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin". J. Chem. Soc. C: 442. doi:10.1039/j39680000442.
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