Capsaicin

Capsaicin
Names


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 (Jmol)	Interactive image
ChEBI	CHEBI:3374^Y
ChEMBL	ChEMBL294199^Y
ChemSpider	1265957^Y
ECHA InfoCard	100.006.337
EC Number	206-969-8
IUPHAR/BPS	2486
KEGG	C06866^Y
PubChem	1548943
UNII	S07O44R1ZM^Y
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	305.42 g·mol⁻¹
Appearance	crystalline white powder
Odor	highly volatile and 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
UV-vis (λ_max)	280 nm
Structure
Crystal structure	monoclinic
Pharmacology
ATC code	M02AB01 (WHO) N01BX04 (WHO)
Hazards
Main hazards	Toxic (T)
Safety data sheet	Capsaicin, Natural MSDS
R-phrases	R24/25
S-phrases	S26, S36/37/39, S45
NFPA 704	1 2 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Capsaicin

Heat	Above Peak (SR: 15,000,000-16,000,000)

Capsaicin (/kæpˈseɪ.ᵻsɪn/ (INN); 8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related compounds are called capsaicinoids and are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi. Pure capsaicin is a volatile, hydrophobic, colorless, odorless, crystalline to waxy compound.

The compound was first extracted in impure form in 1816 by Christian Friedrich Bucholz (1770–1818). He called it "capsicin", after the genus Capsicum from which it was extracted. John Clough Thresh (1850–1932), who had isolated capsaicin in almost pure form, gave it the name "capsaicin" in 1876. Karl Micko isolated capsaicin in its pure form in 1898. Capsaicin's chemical composition was first determined by E. K. Nelson in 1919, who also partially elucidated capsaicin's chemical structure. Capsaicin was first synthesized in 1930 by Ernst Spath and Stephen F. Darling. In 1961, similar substances were isolated from chili peppers by the Japanese chemists S. Kosuge and Y. Inagaki, who named them capsaicinoids.

In 1873 German pharmacologist Rudolf Buchheim (1820–1879) and in 1878 the Hungarian doctor Endre Hőgyes stated that "capsicol" (partially purified capsaicin) caused the burning feeling when in contact with mucous membranes and increased secretion of gastric acid.

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Wikipedia