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Merck

M2028

Capsaicin

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

Sinónimos:

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

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Fórmula lineal:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
Número CAS:
Peso molecular:
305.41
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
206-969-8
MDL number:
Beilstein/REAXYS Number:
2816484
Assay:
≥95%
Quality level:
Servicio técnico
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Nombre del producto

Capsaicin, ≥95%, from Capsicum sp.

biological source

Capsicum sp.

Quality Level

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

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. 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)

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.


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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

Clase de almacenamiento

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



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Contenido relacionado

Product Information Sheet


Capsaicin upregulates HDAC2 via TRPV1 and impairs neuronal maturation in mice.
Wang S, et al.
Experimental & Molecular Medicine, 50(3), e455-e455 (2018)
Shao-Gang Lu et al.
Pain, 151(3), 633-643 (2010-10-05)
The impact of persistent inflammation on voltage-activated Ca(2+) channels in cutaneous DRG neurons from adult rats was assessed with whole cell patch clamp techniques, sqRT-PCR and Western blot analysis. Inflammation was induced with a subcutaneous injection of complete Freund's adjuvant
Stimulation of TRPV1 channels activates the AP-1 transcription factor.
Backes TM, et al.
Biochemical Pharmacology, 150(3), 160-169 (2018)