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360376

Sigma-Aldrich

Capsaicin

natural

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.77

grade

natural

Quality Level

assay

63.7% (HPLC)

form

powder

composition

capsaicin, 65%
dihydrocapsaicin, 35%

mp

62-65 °C (lit.)

solubility

chloroform: 5%

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 (Zostrix), an alkaloid extract is obtained from hot chili peppers. It is accessible in the form of cream and lotion. Capsaicin is a hydrophobic, instable and pungent white crystalline powder, that has no smell and color. It is produced by mixing a branched-chain fatty acid to vanillylamine in the chili pepper.

Application

Capsaicin has been used in the development of the isolation methods. It has also been used in the development of enzyme based electrochemical biosensor for the determination of capsaicin using a novel signal amplification strategy.

Packaging

250 mg in glass insert
1 g in glass bottle

Biochem/physiol Actions

Capsaicin is used as an important component of oleoresin capsicum or pepper spray. It plays a beneficial role in obesity, cardiovascular and gastrointestinal conditions, several cancers, neurogenic bladder and dermatologic conditions. It is used in the production of spices, chilli sauces and pain-inducing defensive pepper sprays. Capsaicin is also used to manufacture creams to treat diabetic neuropathy, cluster headache, psoriasis, rheumatoid arthritis and reflex sympathetic dystrophy. It is considered as an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1).
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

Certificate of Analysis

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Certificate of Origin

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