Dihydrocapsaicin

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
CAS Number
3D model (JSmol)
Beilstein Reference
 2815150
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.115.366
EC Number
  • 606-308-7
KEGG
PubChem CID
RTECS number
  • RA5998000
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • CC(C)CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Properties
Chemical formula
 C18H29NO3
Molar mass 307.43 g/mol
Appearance White to off-white solid
Solubility in water
 Sparingly soluble
Hazards
GHS labelling:
Pictograms
 GHS06: Toxic
Signal word
 Danger
Hazard statements
 H301, H315, H319, H335
Precautionary statements
 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)
NFPA 704 four-colored diamond
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Dihydrocapsaicin
HeatAbove peak
(pure Dihydrocapsaicin is toxic)
Scoville scale16,000,000[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

  1. ^ 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.
  2. ^ Bennett DJ, Kirby GW (1968). "Constitution and biosynthesis of capsaicin". J. Chem. Soc. C: 442. doi:10.1039/j39680000442.
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