Merck
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M2028

Sigma-Aldrich

Capsaicin

≥95%, from Capsicum sp.

Sinônimo(s):
8-Methyl-N-vanillyl-trans-6-nonenamide
Fórmula linear:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
Número CAS:
Peso molecular:
305.41
Beilstein:
2816484
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.77

Nível de qualidade

200

fonte biológica

Capsicum sp.

teor

≥95%

pf

62-65 °C (lit.)

solubilidade

H2O: insoluble
ethanol: soluble

temperatura de armazenamento

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

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Aplicação

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)

Embalagem

1 g in glass bottle
250 mg in glass bottle
50 mg in poly bottle

Ações bioquímicas/fisiológicas

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.

Palavra indicadora

Danger

Classificações de perigo

Acute Tox. 2 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Ponto de fulgor (ºF)

235.4 °F - closed cup

Ponto de fulgor (ºC)

113 °C - closed cup

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificado de análise

Insira o número de lote para pesquisar o Certificado de análise (COA).

Certificado de origem

Insira o número de lote para pesquisar o Certificado de origem (COO).

  1. Which document(s) contains shelf-life or expiration date information for a given product?

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Capsaicin upregulates HDAC2 via TRPV1 and impairs neuronal maturation in mice.
Wang S, et al.
Experimental & Molecular Medicine, 50(3), e455-e455 (2018)
Stimulation of TRPV1 channels activates the AP-1 transcription factor.
Backes TM, et al.
Biochemical Pharmacology, 150(3), 160-169 (2018)
Amol M Patwardhan et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(44), 18820-18824 (2009-10-22)
Transient receptor potential vanilloid 1 (TRPV1) plays a major role in hyperalgesia and allodynia and is expressed both in the peripheral and central nervous systems (CNS). However, few studies have evaluated mechanisms by which CNS TRPV1 mediates hyperalgesia and allodynia
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
Seon-Hee Oh et al.
The Journal of pharmacology and experimental therapeutics, 329(1), 112-122 (2009-01-14)
Endoplasmic reticulum (ER) stress causes cell survival or death, which is dependent on the type of cell and stimulus. Capsaicin (8-methyl-N-vanillyl-6-nonenamide) and its analog, dihydrocapsaicin (DHC), induced caspase-3-independent/-dependent signaling pathways in WI38 lung epithelial fibroblast cells. Here, we describe the

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