Homodihydrocapsaicin Names Preferred IUPAC name N -[(4-Hydroxy-3-methoxyphenyl)methyl]-9-methyldecanamide
Other names Homodihydrocapsaicin N -Vanillyl-9-methyldecanamideVanillylamide of 9-methyldecanoic acid HDHC Identifiers ChemSpider UNII 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
O=C(NCc1cc(OC)c(O)cc1)CCCCCCCC(C)C
Properties C 19 H 31 N O 3 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).
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]
See also
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
TRPA
Activators 4-Hydroxynonenal 4-Oxo-2-nonenal 5,6-EET 12S-HpETE 15-Deoxy-Δ12,14 -prostaglandin J2 α-Sanshool (ginger , Sichuan and melegueta peppers ) Acrolein Allicin (garlic ) Allyl isothiocyanate (mustard , radish , horseradish , wasabi ) AM404 ASP-7663 Bradykinin Cannabichromene (cannabis ) Cannabidiol (cannabis ) Cannabigerol (cannabis ) Cinnamaldehyde (cinnamon ) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin ) Curcumin (turmeric ) Dehydroligustilide (celery ) Diallyl disulfide Dicentrine (Lindera spp.) Farnesyl thiosalicylic acid Formalin Gingerols (ginger ) Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate JT-010 Ligustilide (celery , Angelica acutiloba ) Linalool (Sichuan pepper , thyme ) Methylglyoxal Methyl salicylate (wintergreen ) N-Methylmaleimide Nicotine (tobacco ) Oleocanthal (olive oil ) Paclitaxel (Pacific yew ) Paracetamol (acetaminophen) PF-4840154 Phenacyl chloride Polygodial (Dorrigo pepper ) Shogaols (ginger , Sichuan and melegueta peppers ) Tear gases Tetrahydrocannabinol (cannabis ) Tetrahydrocannabiorcol Thiopropanal S-oxide (onion ) Umbellulone (Umbellularia californica ) WIN 55,212-2 Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators 2-APB 5,6-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α-Sanshool (ginger , Sichuan and melegueta peppers ) Allicin (garlic ) AM404 Anandamide Bisandrographolide (Andrographis paniculata ) Camphor (camphor laurel , rosemary , camphorweed , African blue basil , camphor basil ) Cannabidiol (cannabis ) Cannabidivarin (cannabis ) Capsaicin (chili pepper ) Carvacrol (oregano , thyme , pepperwort , wild bergamot , others) DHEA Diacyl glycerol Dihydrocapsaicin (chili pepper ) Estradiol Eugenol (basil , clove ) Evodiamine (Euodia ruticarpa ) Gingerols (ginger ) GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin (chili pepper ) (chili pepper ) Incensole (incense ) Lysophosphatidic acid Low pH (acidic conditions) Menthol (mint ) N-Arachidonoyl dopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide (PAVA) (PAVA spray ) Nordihydrocapsaicin (chili pepper ) Paclitaxel (Pacific yew ) Paracetamol (acetaminophen) Phenylacetylrinvanil Phorbol esters (e.g., 4α-PDD) Piperine (black pepper , long pepper ) Polygodial (Dorrigo pepper ) Probenecid Protons RhTx Rutamarin (Ruta graveolens ) Resiniferatoxin (RTX) (Euphorbia resinifera /pooissonii ) Shogaols (ginger , Sichuan and melegueta peppers ) Tetrahydrocannabivarin (cannabis ) Thymol (thyme , oregano ) Tinyatoxin (Euphorbia resinifera /pooissonii ) Tramadol Vanillin (vanilla ) Zucapsaicin Blockers
See also: Receptor/signaling modulators • Ion channel modulators