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21750

Sigma-Aldrich

Capsaicin

from Capsicum sp., ≥50% (HPLC)

Synonym(s):

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

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About This Item

Linear Formula:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
CAS Number:
Molecular Weight:
305.41
Beilstein:
2816484
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.25

biological source

Capsicum sp.

form

powder

concentration

≥50% (HPLC)

impurities

~35% dihydrocapsaicin

mp

62-65 °C (lit.)
62-66 °C

solubility

H2O: insoluble

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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.

Biochem/physiol Actions

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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
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
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)

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