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21750

Sigma-Aldrich

Capsaicin

from Capsicum sp., ≥50% (HPLC)

Sinonimo/i:

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

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About This Item

Formula condensata:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
Numero CAS:
404-86-4
Peso molecolare:
305.41
Beilstein:
2816484
Numero CE:
206-969-8
Numero MDL:
MFCD00017259
Codice UNSPSC:
12352200
ID PubChem:
57647941
NACRES:
NA.25

Origine biologica

Capsicum sp.

Livello qualitativo

100

Forma fisica

powder

Concentrazione

≥50% (HPLC)

Impurezze

~35% dihydrocapsaicin

Punto di fusione

62-65 °C (lit.)
62-66 °C

Solubilità

H2O: insoluble

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

2-8°C

Stringa SMILE

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+
YKPUWZUDDOIDPM-SOFGYWHQSA-N

Informazioni sul gene

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

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Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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.

Avvertenze

Danger

Indicazioni di pericolo

H300,H315,H317,H318,H334,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

235.4 °F - closed cup

Punto d’infiammabilità (°C)

113 °C - closed cup

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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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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