:Dihydrocapsaicin

{{Refimprove|date=November 2007}}

{{chembox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 443686495

|ImageFile = Dihydrocapsaicin.svg

|ImageSize = 250px

|PIN = N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide

|OtherNames = Dihydrocapsaicin, 6,7-Dihydrocapsaicin, 8-Methyl-N-vanillylnonanamide, Vanillylamide of 8-methylnonanoic acid, DHC, CCRIS 1589

|Section1={{Chembox Identifiers

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

|CASNo = 19408-84-5

|Beilstein = 2815150

|ChEBI = 46932

|ChEMBL = 311158

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 97096

|EINECS = 606-308-7

|KEGG = C16952

|PubChem = 107982

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

|UNII = W9BV32M08A

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

|RTECS = RA5998000

|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)

|InChIKey = XJQPQKLURWNAAH-UHFFFAOYAI

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

|StdInChI = 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)

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

|StdInChIKey = XJQPQKLURWNAAH-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

|Formula = C₁₈H₂₉NO₃

|MolarMass = 307.43 g/mol

|Appearance = White to off-white solid

|Solubility = Sparingly soluble

}}

|Section3={{Chembox Hazards

|NFPA-H = 2

|NFPA-F = 1

|NFPA-R = 0

|GHSPictograms = {{GHS06}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|301|315|319|335}}

|PPhrases = {{P-phrases|261|264|270|271|280|301+310|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}

}}

}}

{{Infobox pepper

|heat = Above peak
(pure Dihydrocapsaicin is toxic)

|scoville = 16,000,000{{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}}

}}

File:Dihydrocapsaicin UPLC MS-MS journal.pone.0079013.g005.png

Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin, it is an irritant. It accounts for about 22% of the total capsaicinoid 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 the same pungency as capsaicin. Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is soluble in dimethyl sulfoxide and 100% ethanol.