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Capsaicin

Capsaicin
Kapsaicyna.svg
Capsaicin-3D-vdW.png
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
404-86-4 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:3374 YesY
ChEMBL ChEMBL294199 YesY
ChemSpider 1265957 YesY
ECHA InfoCard 100.006.337
EC Number 206-969-8
2486
KEGG C06866 YesY
PubChem 1548943
UNII S07O44R1ZM YesY
Properties
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
0.0013 g/100 mL
Solubility soluble in alcohol, ether, benzene
slightly soluble in CS2, HCl, petroleum
UV-vismax) 280 nm
Structure
monoclinic
Pharmacology
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
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references
Capsaicin
Hottest-chili-rating.gif
Heat Above Peak (SR: 15,000,000-16,000,000)

Capsaicin (/kæpˈs.sɪn/ (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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