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21750

Sigma-Aldrich

Capsaicin

from Capsicum sp., ≥50% (HPLC)

Synonim(y):

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

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About This Item

Wzór liniowy:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
Numer CAS:
404-86-4
Masa cząsteczkowa:
305.41
Beilstein:
2816484
Numer WE:
206-969-8
Numer MDL:
MFCD00017259
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
57647941
NACRES:
NA.25

pochodzenie biologiczne

Capsicum sp.

Poziom jakości

100

Postać

powder

stężenie

≥50% (HPLC)

zanieczyszczenia

~35% dihydrocapsaicin

mp

62-65 °C (lit.)
62-66 °C

rozpuszczalność

H2O: insoluble

Zastosowanie

metabolomics
vitamins, nutraceuticals, and natural products

temp. przechowywania

2-8°C

ciąg 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+

Klucz InChI

YKPUWZUDDOIDPM-SOFGYWHQSA-N

informacje o genach

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

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Opis ogólny

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.

Zastosowanie

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

Działania biochem./fizjol.

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.
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Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H300,H315,H317,H318,H334,H335

Klasyfikacja zagrożeń

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

Organy docelowe

Respiratory system

Kod klasy składowania

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

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

235.4 °F - closed cup

Temperatura zapłonu (°C)

113 °C - closed cup

Środki ochrony indywidualnej

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

Certyfikaty analizy (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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