Homodihydrocapsaicin

Homodihydrocapsaicin
Homodihydrocapsaicin
Heat	Above peak
Scoville scale	8,600,000 SHU

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
CAS Number	20279-06-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	2341417 ;
PubChem CID	3084336;
UNII	QE35S0T20Z ;
CompTox Dashboard (EPA)	DTXSID30174127 ;
	InChI 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) Key: AKDLSISGGARWFP-UHFFFAOYSA-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;
	SMILES O=C(NCc1cc(OC)c(O)cc1)CCCCCCCC(C)C;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

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.

External links

Molecule of the Month

[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.

[2]

[1]

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
CAS Number	20279-06-5^Y
3D model (JSmol)	Interactive image
ChemSpider	2341417^N
PubChem CID	3084336
UNII	QE35S0T20Z^Y
CompTox Dashboard (EPA)	DTXSID30174127
InChI 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
SMILES O=C(NCc1cc(OC)c(O)cc1)CCCCCCCC(C)C
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references

Homodihydrocapsaicin

See also

References

External links