M2028

Capsaicin

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

• 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
• NACRES: NA.77
• PubChem Substance ID: 24896598
• UNSPSC Code: 12352200
• EC Number: 206-969-8
• MDL number: MFCD00017259
• Beilstein/REAXYS Number: 2816484
• Assay: ≥95%

Properties

• Product Name: Capsaicin, ≥95%, from Capsicum sp.
• biological source: Capsicum sp.
• Quality Segment: 200
• assay: ≥95%
• mp: 62-65 °C (lit.)
• solubility: H₂O: insoluble, ethanol: soluble
• 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 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.[1] Capsaicin activates its receptor transient receptorpotential vanilloid subfamily member 1 (TRPV1) and activates sensory afferentneurons[2] 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.[3]

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)

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.

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: 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