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Dihydrocapsaicin

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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
3D model (JSmol)
2815150
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.115.366Edit this at Wikidata
EC Number
  • 606-308-7
KEGG
RTECS number
  • RA5998000
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
C18H29NO3
Molar mass307.43 g/mol
AppearanceWhite to off-white solid
Sparingly soluble
Hazards
GHS labelling:
GHS06: Toxic
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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound
Dihydrocapsaicin
HeatAbove peak
(pure Dihydrocapsaicin istoxic)
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 andcongener ofcapsaicin inchili peppers (Capsicum). Like capsaicin, it is anirritant. It accounts for about 22% of the total capsaicinoid mixture[2] and has the same pungency as capsaicin.[1] Pure dihydrocapsaicin is alipophilic colorless odorless crystalline to waxy compound. It is soluble indimethyl sulfoxide and 100%ethanol.

See also

[edit]

References

[edit]
  1. ^abGovindarajan, 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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