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Capsaicin information


Capsaicin
Names
Pronunciation /kæpˈssɪn/ or /kæpˈsəsɪn/
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 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
2816484
ChEBI
  • CHEBI:3374 checkY
ChEMBL
  • ChEMBL294199 checkY
ChemSpider
  • 1265957 checkY
DrugBank
  • DB06774
ECHA InfoCard 100.006.337 Edit this at Wikidata
EC Number
  • 206-969-8
IUPHAR/BPS
  • 2486
KEGG
  • C06866 checkY
PubChem CID
  • 1548943
UNII
  • S07O44R1ZM checkY
CompTox Dashboard (EPA)
  • DTXSID9020241 Edit this at Wikidata
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+ 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
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[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
Solubility in water
0.0013 g/100mL
Solubility
  • Soluble in alcohol, ether, benzene
  • Slightly soluble in CS2, HCl, petroleum
Vapor pressure 1.32×10−8 mm Hg at 25 °C[2]
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[3][4]
Hazards
GHS labelling:
Pictograms
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
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)
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 ?)
Infobox references
Capsaicin
HeatAbove peak
(pure capsaicin is toxic)[2]
Scoville scale16,000,000[5] SHU

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) (/kæpˈssɪn/ or /kæpˈsəsɪn/) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a chemical irritant and neurotoxin[6] 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.[7] 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. ^ Ritter S, Dinh TT (June 1990). "Capsaicin-induced neuronal degeneration in the brain and retina of preweanling rats". The Journal of Comparative Neurology. 296 (3): 447–461. doi:10.1002/cne.902960310. PMID 2358547. S2CID 5468197.
  7. ^ "What Made Chili Peppers So Spicy?". Talk of the Nation. 15 August 2008.

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Capsaicin

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Capsaicin (8-methyl-N-vanillyl-6-nonenamide) (/kæpˈseɪsɪn/ or /kæpˈseɪəsɪn/) is an active component of chili peppers, which are plants belonging to the...

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Scoville scale

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(SHU). It is based on the concentration of capsaicinoids, among which capsaicin is the predominant component. The scale is named after its creator, American...

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Capsicum

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produce any capsaicin, although the highest concentration of capsaicin can be found in the white pith around the seeds. Most of the capsaicin in a pungent...

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Chili pepper

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are widely used in many cuisines as a spice to add "heat" to dishes. Capsaicin and related compounds known as capsaicinoids are the substances that give...

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Pungency

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mustard and curry. The primary substances responsible for pungent taste are capsaicin, piperine (in peppers) and allyl isothiocyanate (in radish, mustard and...

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Pepper X

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several cross breedings that produced an exceptionally high content of capsaicin in the locules – the plant tissue holding the seeds. The extensive curves...

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TRPV1

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potential cation channel subfamily V member 1 (TRPV1), also known as the capsaicin receptor and the vanilloid receptor 1, is a protein that, in humans, is...

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Pepper spray

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capsicum spray, OC spray, capsaicin spray, or capsicum spray is a lachrymator (tear gas) product containing the compound capsaicin as the active ingredient...

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Resiniferatoxin

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poissonii found in northern Nigeria. It is a potent functional analog of capsaicin, the active ingredient in chili peppers. Resiniferatoxin has a score of...

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Bear spray

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ingredients are highly irritant capsaicin and related capsaicinoids, that is used to deter aggressive or charging bears. Capsaicin bear spray was developed in...

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Capsinoid

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naturally present in chili peppers. Although they are structurally similar to capsaicin, the substance that causes pungency in hot peppers, they largely lack...

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Bell pepper

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pepper is the only member of the genus Capsicum that does not produce capsaicin, a lipophilic chemical that can cause a strong burning sensation when...

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Capsicum annuum

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Similar to other variants the Chiltepin pepper produces and contains capsaicin which is responsible for its intense heat ranging from 100,000 to 200...

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Arthralgia

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symptoms. Capsaicin, a substance found in chili peppers, may relieve joint pain from arthritis[citation needed] and other conditions. Capsaicin blocks the...

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Tinyatoxin

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similar to uses of capsaicin. Tinyatoxin is about one third as strong as resiniferatoxin but is still an ultrapotent analogue of capsaicin, with a heat intensity...

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Ghost pepper

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For comparison, Tabasco red pepper sauce rates at 2,500–5,000, and pure capsaicin (the chemical responsible for the pungency of pepper plants) rates at...

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Dihydrocapsaicin

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Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin, it is an irritant. It accounts for about 22% of...

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Nordihydrocapsaicin

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Nordihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin, it is an irritant. Nordihydrocapsaicin accounts...

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Zucapsaicin

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vanilloid or capsaicin receptor 1 that reduces pain, and improves articular functions.[unreliable medical source?] It is the cis-isomer of capsaicin. Civamide...

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Nonivamide

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but is commonly manufactured synthetically. It is more heat-stable than capsaicin. Nonivamide is used as a food additive to add pungency to seasonings,...

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Vanillylamine

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is a chemical compound that is an intermediate in the biosynthesis of capsaicin. Vanillylamine is produced from vanillin by the enzyme vanillin aminotransferase...

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Postherpetic neuralgia

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is the main goal of treatment. Medications applied to the skin such as capsaicin or topical anesthetics (e.g., lidocaine) are used for mild pain and can...

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Homodihydrocapsaicin

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Homodihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Homodihydrocapsaicin accounts...

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David Julius

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including the characterization of the TRPV1 and TRPM8 receptors that detect capsaicin, menthol, and temperature. He is a professor at the University of California...

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Hottest chili pepper

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this is not true. Super-hots not only have more capsaicin than other peppers, but also store their capsaicin differently. In their report, Bosland et al....

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Notalgia paresthetica

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the condition. Available treatments include local anesthetics, topical capsaicin, topical corticosteroids, hydroxyzine, oxcarbazepine, palmitoylethanolamide...

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Crushed red pepper

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crushed red pepper contains fiber, capsaicin—the source of the heat in pepper chilis—and vitamins A, C, and B6. Capsaicin is believed to help kill off prostate...

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Hot sauce

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2017. Capsaicin extract - The hottest sauces are made from capsaicin extract. These range from extremely hot pepper sauce blends to pure capsaicin extracts...

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Gochujang

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gas chromatography and the high-performance liquid chromatography of capsaicin and dihydrocapsaicin concentrations. Gochujang products are assigned to...

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Hunan hand syndrome

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England Journal of Medicine in 1981. It occurs when the phytochemical capsaicin, which can be present in very high concentrations in certain varieties...

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