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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
Drug
Identifiers
3D model (JSmol)
2816484
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.337 Edit this at Wikidata
EC Number
  • 206-969-8
KEGG
UNII
  • 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+ checkY
    Key: YKPUWZUDDOIDPM-SOFGYWHQSA-N checkY
  • 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
  • O=C(NCc1cc(OC)c(O)cc1)CCCC/C=C/C(C)C
Properties
C18H27NO3
Molar mass 305.418 g·mol−1
Appearance Crystalline white powder[1]
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
0.0013 g/100 mL
Solubility
Vapor pressure 1.32×10−8 mm Hg at 25 °C[2]
UV-vis (λmax) 280 nm
Structure
Monoclinic
Pharmacology
M02AB01 (WHO) N01BX04 (WHO)
License data
Legal status
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H302, H315, H318
P264, P270, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Safety data sheet (SDS) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Capsaicin
HeatAbove peak
(pure capsaicin is toxic)[2]
Scoville scale16,000,000[5] SHU

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) (/kæpˈseɪsɪn/ or /kæpˈseɪəsɪn/) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a potent irritant for mammals, including humans, and 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 certain mammals and fungi.[6] Pure capsaicin is a hydrophobic, colorless, highly pungent (i.e., spicy) crystalline solid.[2]

  1. ^ "Capsaicin". ChemSpider, Royal Society of Chemistry, Cambridge, UK. 2018. Retrieved 9 June 2018.
  2. ^ a b c d "Capsaicin". PubChem, US National Library of Medicine. 27 May 2023. Retrieved 1 June 2023.
  3. ^ "Qutenza- capsaicin kit". DailyMed. 10 January 2023. Retrieved 22 February 2023.
  4. ^ "Drug Approval Package: Qutenza (capsaicin) NDA #022395". U.S. Food and Drug Administration (FDA). 3 October 2013. Retrieved 22 February 2023.
  5. ^ Govindarajan VS, Sathyanarayana MN (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.
  6. ^ "What Made Chili Peppers So Spicy?". Talk of the Nation. 15 August 2008.

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