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21750

Sigma-Aldrich

Capsaicin

from Capsicum sp., ≥50% (HPLC)

Synonyme(s) :

8-Methyl-N-vanillyl-trans-6-nonenamide

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About This Item

Formule linéaire :
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
Numéro CAS:
404-86-4
Poids moléculaire :
305.41
Beilstein:
2816484
Numéro CE :
206-969-8
Numéro MDL:
MFCD00017259
Code UNSPSC :
12352200
ID de substance PubChem :
57647941
Nomenclature NACRES :
NA.25

Source biologique

Capsicum sp.

Niveau de qualité

100

Forme

powder

Concentration

≥50% (HPLC)

Impuretés

~35% dihydrocapsaicin

Pf

62-65 °C (lit.)
62-66 °C

Solubilité

H2O: insoluble

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

2-8°C

Chaîne SMILES 

COc1cc(CNC(=O)CCCC\C=C\C(C)C)ccc1O

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+

Clé InChI

YKPUWZUDDOIDPM-SOFGYWHQSA-N

Informations sur le gène

human ... CYP1A2(1544) , TRPV1(7442)
rat ... Trpv1(83810) , Trpv4(66026)

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Description générale

Capsaicin occurs as the active ingredient of hot/red pepper and was first obtained by Thresh in 1846. It is a lipophilic vanilloid compound responsible for the acrid taste of hot peppers.

Application

Capsaicin has been used in the development and pharmaceutical production of a gastrointestinal mucosal protective drug.

Actions biochimiques/physiologiques

Capsaicin shows its activity by binding to vanilloid receptors and eliciting a nociceptive response. It shows an analgesic effect in neuropathic and musculoskeletal disorders. Capsaicin is also used in the management of bladder detrusor hyperreflexia.
Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.

Pictogrammes

Skull and crossbonesHealth hazardCorrosion
GHS06,GHS08,GHS05

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 2 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

235.4 °F - closed cup

Point d'éclair (°C)

113 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
BCCD6805
BCBJ2271V
BCBH7471V
1437650V
1437650

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Dihydrocapsaicin phyproof® Reference Substance

PHL89647

Dihydrocapsaicin

N-Vanillylnonanamide analytical standard

Supelco

15971

N-Vanillylnonanamide

Capsazepine ≥98% (HPLC), solid

Sigma-Aldrich

C191

Capsazepine

Dihydrocapsaicin United States Pharmacopeia (USP) Reference Standard

USP

1200600

Dihydrocapsaicin

N-Vanillylnonanamide ≥97%, powder

Sigma-Aldrich

V9130

N-Vanillylnonanamide

Nordihydrocapsaicin phyproof® Reference Substance

PHL89254

Nordihydrocapsaicin

Acrylonitrile ≥99%, contains 35-45 ppm monomethyl ether hydroquinone as inhibitor

Sigma-Aldrich

110213

Acrylonitrile

Histamine ≥97.0%

Sigma-Aldrich

H7125

Histamine

Lorna Mason et al.
BMJ (Clinical research ed.), 328(7446), 991-991 (2004-03-23)
To determine the efficacy and safety of topically applied capsaicin for chronic pain from neuropathic or musculoskeletal disorders. Cochrane Library, Medline, Embase, PubMed, an in-house database, and contact with manufacturers of topical capsaicin. Randomised controlled trials comparing topically applied capsaicin
S W Hwang et al.
Proceedings of the National Academy of Sciences of the United States of America, 97(11), 6155-6160 (2000-05-24)
Capsaicin, a pungent ingredient of hot peppers, causes excitation of small sensory neurons, and thereby produces severe pain. A nonselective cation channel activated by capsaicin has been identified in sensory neurons and a cDNA encoding the channel has been cloned
Jennifer Leech et al.
American journal of respiratory and critical care medicine, 188(9), 1069-1075 (2013-10-08)
Antitussive therapies are accompanied by a substantial placebo effect, indicating that inhibitory circuits in the brain have a significant capacity to regulate cough neural processing. However, essentially nothing is known about the identity of these inhibitory circuits or how they
Emma C Y Hilton et al.
The Journal of allergy and clinical immunology, 132(4), 847-855 (2013-06-20)
Inhaled capsaicin elicits cough reproducibly in human subjects and is widely used in the study of cough and antitussive therapies. However, the traditional end points C2 and C5 (the concentrations of capsaicin inducing at least 2 or 5 coughs, respectively)
Jessica O'Neill et al.
Pharmacological reviews, 64(4), 939-971 (2012-10-02)
A large number of pharmacological studies have used capsaicin as a tool to activate many physiological systems, with an emphasis on pain research but also including functions such as the cardiovascular system, the respiratory system, and the urinary tract. Understanding
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