Homocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Homocapsaicin accounts for about 1% of the total capsaicinoids mixture[2] and has about half the pungency of capsaicin. Pure homocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. On the Scoville scale it has 8,600,000 SHU (Scoville heat units).[1] Homocapsaicin isolated from chili pepper has been found in two isomeric forms, both with a carbon-carbon double bond at the 6 position (numbered from the amide carbon) on the 10-carbon acyl chain. One isomer has an additional carbon, a methyl group, at the 8 position and the other has a methyl group at the 9 position. Homocapsaicin (6-ene-8-methyl) is the more abundant isomer. Homocapsaicin with the double bond at the 7 position has never been found in nature, though its structure is widely reported on the Internet and in the scientific literature. Details of this misidentification have been published.[3]
Homocapsaicin II, N-Vanillyl-8-methyldec-6-(E)-enamide, trans-N-Vanillyl-8-methyldec-6-enamide, N-(4-Hydroxy-3-methoxybenzyl)-8-methyldec-trans-6-enamide, Vanillylamide of 8-methyldec-trans-6-enoic acid, HC
^ abGovindarajan, 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.
^Thompson, Robert Q (2007). "Homocapsaicin: Nomenclature, indexing and identification". Flavour and Fragrance Journal. 22 (4): 243–248. doi:10.1002/ffj.1814.
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Molecule of the Month
January 01, 1970
homocapsaicin, capsaicinoid, analog, congener, capsaicin, chili, peppers, capsicum, like, capsaicin, irritant, accounts, about, total, capsaicinoids, mixture, about, half, pungency, capsaicin, pure, homocapsaicin, lipophilic, colorless, odorless, crystalline, . Homocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers Capsicum Like capsaicin it is an irritant Homocapsaicin accounts for about 1 of the total capsaicinoids mixture 2 and has about half the pungency of capsaicin Pure homocapsaicin is a lipophilic colorless odorless crystalline to waxy compound On the Scoville scale it has 8 600 000 SHU Scoville heat units 1 Homocapsaicin isolated from chili pepper has been found in two isomeric forms both with a carbon carbon double bond at the 6 position numbered from the amide carbon on the 10 carbon acyl chain One isomer has an additional carbon a methyl group at the 8 position and the other has a methyl group at the 9 position Homocapsaicin 6 ene 8 methyl is the more abundant isomer Homocapsaicin with the double bond at the 7 position has never been found in nature though its structure is widely reported on the Internet and in the scientific literature Details of this misidentification have been published 3 Homocapsaicin Names IUPAC name 6E N 4 Hydroxy 3 methoxybenzyl 8 methyldec 6 enamide Other names Homocapsaicin II N Vanillyl 8 methyldec 6 E enamide trans N Vanillyl 8 methyldec 6 enamide N 4 Hydroxy 3 methoxybenzyl 8 methyldec trans 6 enamide Vanillylamide of 8 methyldec trans 6 enoic acid HC Identifiers CAS Number 58493 48 4 Y 3D model JSmol Interactive image ChemSpider 9848876 Y PubChem CID 11674147 UNII S5KLC0JPH3 Y CompTox Dashboard EPA DTXSID50894012 InChI InChI 1S C19H29NO3 c1 4 15 2 9 7 5 6 8 10 19 22 20 14 16 11 12 17 21 18 13 16 23 3 h7 9 11 13 15 21H 4 6 8 10 14H2 1 3H3 H 20 22 b9 7 YKey MLJGZARGNROKAC VQHVLOKHSA N YInChI 1 C19H29NO3 c1 4 15 2 9 7 5 6 8 10 19 22 20 14 16 11 12 17 21 18 13 16 23 3 h7 9 11 13 15 21H 4 6 8 10 14H2 1 3H3 H 20 22 b9 7 Key MLJGZARGNROKAC VQHVLOKHBL SMILES O C NCC1 CC OC C O C C1 CCCC C C C CC C Properties Chemical formula C19H29NO3 Molar mass 319 43 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references HomocapsaicinHeatAbove peakScoville scale8 600 000 1 SHUSee also editDihydrocapsaicin Nordihydrocapsaicin Homodihydrocapsaicin Scoville scale Pepper spray SpiceReferences edit 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 Thompson Robert Q 2007 Homocapsaicin Nomenclature indexing and identification Flavour and Fragrance Journal 22 4 243 248 doi 10 1002 ffj 1814 External links editMolecule of the Month Retrieved from https en wikipedia org w index php title Homocapsaicin amp oldid 1180265060, wikipedia, wiki, book, books, library,
