Capsaicin

Capsaicin

Names
Pronunciation	/kæpˈseɪsɪn/ or /kæpˈseɪəsɪn/
Preferred IUPAC name (6E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Other names (E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide 8-Methyl-N-vanillyl-trans-6-nonenamide trans-8-Methyl-N-vanillylnon-6-enamide (E)-Capsaicin Capsicine Capsicin CPS
Identifiers
CAS Number	404-86-4 Y
3D model (JSmol)	Interactive image
Beilstein Reference	2816484
ChEBI	CHEBI:3374 Y
ChEMBL	ChEMBL294199 Y
ChemSpider	1265957 Y
DrugBank	DB06774
ECHA InfoCard	100.006.337
EC Number	206-969-8
IUPHAR/BPS	2486
KEGG	C06866 Y
PubChem CID	1548943
UNII	S07O44R1ZM Y
CompTox Dashboard (EPA)	DTXSID9020241
InChI InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+ Y Key: YKPUWZUDDOIDPM-SOFGYWHQSA-N Y InChI=1/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+ Key: YKPUWZUDDOIDPM-SOFGYWHQBQ
SMILES O=C(NCc1cc(OC)c(O)cc1)CCCC/C=C/C(C)C
Properties
Chemical formula	C18H27NO3
Molar mass	305.418 g·mol−1
Appearance	Crystalline white powder
Odor	Highly pungent
Melting point	62 to 65 °C (144 to 149 °F; 335 to 338 K)
Boiling point	210 to 220 °C (410 to 428 °F; 483 to 493 K) 0.01 Torr
Solubility in water	0.0013 g/100 mL
Solubility	Soluble in alcohol, ether, benzene Slightly soluble in CS2, HCl, petroleum
Vapor pressure	1.32×10−8 mm Hg at 25 °C
UV-vis (λmax)	280 nm
Structure
Crystal structure	Monoclinic
Pharmacology
ATC code	M02AB01 (WHO) N01BX04 (WHO)
License data	EU EMA: by INN
Legal status	US: ℞-only
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H315, H318
Precautionary statements	P264, P270, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P405, P501
NFPA 704 (fire diamond)	2 1 0
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Capsaicin
Heat	Above peak
Scoville scale	16,000,000 SHU

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) (/kæpˈseɪ.ə.sɪn/, commonly /kæpˈseɪsɪn/) is a toxin that is the main active component of chili peppers and gives them their distinct pungent, "spicy" or "hot" taste. It is a potent irritant for mammals for which it produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, likely as deterrents against eating by mammals and against the growth of fungi. Pure capsaicin is a hydrophobic, highly pungent (i.e., spicy) crystalline solid.