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21750

Sigma-Aldrich

Capsaicin

from Capsicum sp., ≥50% (HPLC)

Synonym(s):
8-Methyl-N-vanillyl-trans-6-nonenamide
Linear Formula:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
CAS Number:
Molecular Weight:
305.41
Beilstein:
2816484
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

biological source

Capsicum sp.

assay

≥50% (HPLC)

form

powder

impurities

~35% dihydrocapsaicin

mp

62-65 °C (lit.)
62-66 °C

solubility

H2O: insoluble

storage temp.

2-8°C

SMILES string

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+

InChI key

YKPUWZUDDOIDPM-SOFGYWHQSA-N

Gene Information

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General description

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.

Packaging

100 mg in glass bottle
1, 5 g in glass bottle

Biochem/physiol Actions

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.
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.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

M J Caterina et al.
Science (New York, N.Y.), 288(5464), 306-313 (2000-04-15)
The capsaicin (vanilloid) receptor VR1 is a cation channel expressed by primary sensory neurons of the "pain" pathway. Heterologously expressed VR1 can be activated by vanilloid compounds, protons, or heat (>43 degrees C), but whether this channel contributes to chemical
Capsaicin is a New Gastrointestinal Mucosal Protecting Drug Candidate in Humans?Pharmaceutical Development and Production Based on Clinical Pharmacology
Capsaicin-sensitive Neural Afferentation and the Gastrointestinal Tract: From Bench to Bedside (2014)
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

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