Nordihydrocapsaicin

Nordihydrocapsaicin
Heat	Above peak
Scoville scale	9,100,000 SHU

Nordihydrocapsaicin
Names
	IUPAC name N-(4-Hydroxy-3-methoxybenzyl)-7-methyloctanamide
	Other names N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide; N-Vanillyl-7-methyloctanamide; Vanillylamide of 7-methyloctanoic acid; NDHC
Identifiers
CAS Number	28789-35-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	147689 ;
ECHA InfoCard	100.208.673
PubChem CID	168836;
UNII	RF657P8DA8 ;
CompTox Dashboard (EPA)	DTXSID3042217 ;
	InChI 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) Key: VQEONGKQWIFHMN-UHFFFAOYSA-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;
	SMILES CC(C)CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC;
Properties
Chemical formula	C17H27NO3
Molar mass	293.407 g·mol−1
Solubility in water	Negligible
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Properties

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 compound. On the Scoville scale it has 9,100,000 SHU (Scoville heat units),^[1] significantly higher than pepper spray.

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.

[Govindarajan_Sathyanarayana_1991-1] 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.

[1]

[2]

Names

IUPAC name N-(4-Hydroxy-3-methoxybenzyl)-7-methyloctanamide
Other names N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide; N-Vanillyl-7-methyloctanamide; Vanillylamide of 7-methyloctanoic acid; NDHC
Identifiers
CAS Number	28789-35-7
3D model (JSmol)	Interactive image
ChemSpider	147689
ECHA InfoCard	100.208.673
PubChem CID	168836
UNII	RF657P8DA8
CompTox Dashboard (EPA)	DTXSID3042217
InChI 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) Key: VQEONGKQWIFHMN-UHFFFAOYSA-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
SMILES CC(C)CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
Properties
Chemical formula	C₁₇H₂₇NO₃
Molar mass	293.407 g·mol⁻¹
Solubility in water	Negligible
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nordihydrocapsaicin

Properties

See also

References