M2028

Capsaicin

from Capsicum sp., ≥95% (HPLC), powder, TRPV1 agonist

• Synonyme(s) : 8-Methyl-N-vanillyl-trans-6-nonenamide
• Formule linéaire : (CH₃)₂CHCH=CH(CH₂)₄CONHCH₂C₆H₃-4-(OH)-3-(OCH₃)
• Numéro CAS: 404-86-4
• Poids moléculaire : 305.41
• Numéro Beilstein : 2816484
• Numéro CE : 206-969-8
• Numéro MDL: MFCD00017259
• Code UNSPSC : 12352200
• ID de substance PubChem : 24896598
• Nomenclature NACRES : NA.77

Propriétés

• product name: Capsaicin, ≥95%, from Capsicum sp.
• Source biologique: Capsicum sp.
• Pureté: ≥95%
• Pf: 62-65 °C (lit.)
• Solubilité: H₂O: insoluble; ethanol: soluble
• Température de stockage: 2-8°C
• Chaîne SMILES: 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+
• Clé InChI: YKPUWZUDDOIDPM-SOFGYWHQSA-N
• Informations sur le gène: human ... CYP1A2(1544) , TRPV1(7442) ; rat ... Trpv1(83810) , Trpv4(66026)

Description

Description générale

Capsaicin is an alkaloid that is present inthe fruit of the Capsicum genus and is the main reason for the spicy flavor inhot peppers including jalapenos, habaneros, and red chili peppers. It isobserved that capsaicin acts as a chemoprotective agent and can induceapoptosis, inhibit proliferation, and induce cell-cycle arrest in variouscancer cells. Capsaicin activates its receptor transient receptorpotential vanilloid subfamily member 1 (TRPV1) and activates sensory afferentneurons that causes neurogenicinflammation, hypothermia, and pain.

Application

Capsaicin has also been used asa TRPV1 agonist to study the effect of barbamide on capsaicin response indorsal root ganglion sensory neurons.

Capsaicin has been used:

• to study its effects on chromatin remodeling and gene expression related to synaptic plasticity
• to study TRPV1 channel signaling in H2C1 cells (which are human embryonic kidney 293 cells expressing TRPV1 channels)

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08,GHS05
• Mention d'avertissement: Danger
• Mentions de danger: H300,H315,H317,H318,H334,H335
• Conseils de prudence: P261 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Acute Tox. 2 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 235.4 °F - closed cup
• Point d'éclair (°C): 113 °C - closed cup
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges