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Capsaicin

SIGMA/21750 - from Capsicum sp., ≥50% (HPLC)

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

CAS Number: 404-86-4
Empirical Formula (Hill Notation): C18H27NO3
Molecular Weight: 305.41
EC Number: 206-969-8
MDL Number: MFCD00017259
Linear Formula: (CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-21750-100MG-F 100 mg
 $0.00
1/EA
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45-21750-1G-F 1 g
 $0.00
1/EA
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application(s) metabolomics
vitamins, nutraceuticals, and natural products
biological source Capsicum sp.
concentration ≥50% (HPLC)
form powder
impurities ~35% dihydrocapsaicin
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
mp 62-65 °C (lit.)
  62-66 °C
Quality Level 100 
SMILES string COc1cc(CNC(=O)CCCCC=CC(C)C)ccc1O
solubility H2O: insoluble
storage temp. 2-8°C
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.
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.
Biochem/physiol Actions: Prototype vanilloid receptor agonist; neurotoxin. Active component of chili peppers.
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.
Packaging: 1, 5 g in glass bottle
Packaging: 100 mg in glass bottle
mp 62-65 °C (lit.); 62-66 °C
Storage Temp. 2-8°C
UNSPSC 12352200

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