Nordihydrocapsaicin

{{short description|Chemical compound}}

{{chembox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 424688122

|ImageFile = Nordihydrocapsaicin chemical structure.png

|ImageSize = 250px

|PIN = N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide

|OtherNames = N-Vanillyl-7-methyloctanamide; Vanillylamide of 7-methyloctanoic acid; NDHC

|Section1 = {{Chembox Identifiers

|CASNo_Ref = {{cascite|correct|??}}

|CASNo = 28789-35-7

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = RF657P8DA8

|PubChem = 168836

|SMILES = CC(C)CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC

|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

|ChemSpiderID = 147689

|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)

|InChIKey = VQEONGKQWIFHMN-UHFFFAOYAS

|StdInChI_Ref = {{stdinchicite|changed|chemspider}}

|StdInChI = 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)

|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

|StdInChIKey = VQEONGKQWIFHMN-UHFFFAOYSA-N

}}

|Section2 = {{Chembox Properties

|C=17|H=27|N=1|O=3

|Solubility = Negligible

|SolubleOther = Soluble in DMSO, chloroform

}}

|Section3 = {{Chembox Hazards

|GHSPictograms = {{GHS06}} {{GHS07}}

|HPhrases = {{H-phrases|300|315|319|335}}

|PPhrases = {{P-phrases|264|270|280|321|330|302+352|362+364|305+351+338|405|501}}

|NFPA-H = 4

|NFPA-F = 0

|NFPA-I = 0

}}

}}

{{Infobox pepper

|heat = Above peak
(pure Nordihydrocapsaicin is highly toxic)

|scoville = 9,100,000{{cite journal | vauthors = Govindarajan, Sathyanarayana | date = 1991 | title = Capsicum — Production, Technology, Chemistry, and Quality. Part V. Impact on Physiology, Pharmacology, Nutrition, and Metabolism; Structure, Pungency, Pain, and Desensitization Sequences | journal = Critical Reviews in Food Science and Nutrition | volume = 29 | issue = 6 | pages = 435–474 | doi=10.1080/10408399109527536 | pmid = 2039598}}

}}

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{{cite journal | vauthors = Bennett DJ, Kirby GW | year = 1968 | title = Constitution and biosynthesis of capsaicin| journal = J. Chem. Soc. C | pages = 442 | doi = 10.1039/j39680000442 }} 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), significantly higher than pepper spray.

See also

References

{{Reflist|2}}

{{Organic-compound-stub}}

{{Transient receptor potential channel modulators}}

Category:Capsaicinoids

Category:Acetamides