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Dihydrocapsaicin
Names
Preferred IUPAC name
N -[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide
Other names
Dihydrocapsaicin, 6,7-Dihydrocapsaicin, 8-Methyl-N -vanillylnonanamide, Vanillylamide of 8-methylnonanoic acid, DHC, CCRIS 1589
Identifiers
2815150
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.115.366
EC Number
KEGG
RTECS number
UNII
InChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)
N Key: XJQPQKLURWNAAH-UHFFFAOYSA-N
N InChI=1/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)
Key: XJQPQKLURWNAAH-UHFFFAOYAI
CC(C)CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Properties
C18 H29 NO3
Molar mass
307.43 g/mol
Appearance
White to off-white solid
Sparingly soluble
Hazards
GHS labelling :
Danger
H301 ,
H315 ,
H319 ,
H335
P261 ,
P264 ,
P270 ,
P271 ,
P280 ,
P301+P310 ,
P302+P352 ,
P304+P340 ,
P305+P351+P338 ,
P312 ,
P321 ,
P330 ,
P332+P313 ,
P337+P313 ,
P362 ,
P403+P233 ,
P405 ,
P501
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Dihydrocapsaicin Heat Above peak (pure Dihydrocapsaicin is toxic )
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 . It 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
^
a
b 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.
doi :
10.1080/10408399109527536 .
PMID
2039598 .
^ Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin". J. Chem. Soc. C : 442.
doi :
10.1039/j39680000442 .
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