Homodihydrocapsaicin

Homodihydrocapsaicin
Names
Preferred IUPAC name
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-9-methyldecanamide
Other names
  • Homodihydrocapsaicin
  • N-Vanillyl-9-methyldecanamide
  • Vanillylamide of 9-methyldecanoic acid
  • HDHC
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C19H31NO3/c1-15(2)9-7-5-4-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h11-13,15,21H,4-10,14H2,1-3H3,(H,20,22) ☒N
    Key: AKDLSISGGARWFP-UHFFFAOYSA-N ☒N
  • InChI=1/C19H31NO3/c1-15(2)9-7-5-4-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h11-13,15,21H,4-10,14H2,1-3H3,(H,20,22)
    Key: AKDLSISGGARWFP-UHFFFAOYAS
  • O=C(NCc1cc(OC)c(O)cc1)CCCCCCCC(C)C
Properties
C19H31NO3
Molar mass 321.461 g·mol−1
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
Homodihydrocapsaicin
HeatAbove peak
Scoville scale8,600,000[1] SHU

Homodihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Homodihydrocapsaicin accounts for about 1% of the total capsaicinoids mixture[2] and has about half the pungency of capsaicin. Pure homodihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It produces "numbing burn" in the throat and is one of the most prolonged and difficult to rinse out. On the Scoville scale it has 8,600,000 SHU (Scoville heat units).[1]

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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