Nordihydrocapsaicin

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Nordihydrocapsaicin
Nordihydrocapsaicin chemical structure.png
Names
Preferred IUPAC name
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide
Other names
N-Vanillyl-7-methyloctanamide; Vanillylamide of 7-methyloctanoic acid; NDHC
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.208.673 Edit this at Wikidata
UNII
  • InChI=1S/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20) ☒N
    Key: VQEONGKQWIFHMN-UHFFFAOYSA-N ☒N
  • InChI=1/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)
    Key: VQEONGKQWIFHMN-UHFFFAOYAS
  • CC(C)CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Properties
C17H27NO3
Molar mass 293.407 g·mol−1
Negligible
Solubility Soluble in DMSO, chloroform
Hazards
GHS labelling:
GHS06: Toxic GHS07: Exclamation mark
H300, H315, H319, H335
P264, P270, P280, P302+P352, P305+P351+P338, P321, P330, P362+P364, P405, P501
NFPA 704 (fire diamond)
4
0
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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Nordihydrocapsaicin
Hottest-chili-rating.gif
HeatAbove peak
Scoville scale9,100,000[1] SHU

Nordihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum).

Properties[edit]

Like capsaicin, it is an irritant. Nordihydrocapsaicin accounts for about 7% of the total capsaicinoids mixture[2] and has about half the pungency of capsaicin. Pure nordihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy solid. On the Scoville scale it has 9,100,000 SHU (Scoville heat units),[1] significantly higher than pepper spray.

See also[edit]

References[edit]

  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.