21750

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: 404-86-4
• Molecular Weight: 305.41
• Beilstein/REAXYS Number: 2816484
• EC Number: 206-969-8
• MDL number: MFCD00017259
• UNSPSC Code: 12352200
• PubChem Substance ID: 57647941
• NACRES: NA.25

Properties

• biological source: Capsicum sp.
• Quality Level: 100
• 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: human ... CYP1A2(1544), TRPV1(7442) ; rat ... Trpv1(83810), Trpv4(66026)

Description

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.

Prototype vanilloid receptor agonist; neurotoxin. Active component of chili peppers.

Safety Information

• pictograms: GHS06,GHS08,GHS05
• signalword: Danger
• hcodes: H300,H315,H317,H318,H334,H335
• pcodes: P261 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• 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: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 235.4 °F - closed cup
• flash_point_c: 113 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges