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Merck

M2028

Capsaicin

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

Synonyme(s) :

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

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A propos de cet article

Formule linéaire :
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
Numéro CAS:
404-86-4
Poids moléculaire :
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%
Quality level:
200

Principaux documents

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Nom du produit

Capsaicin, ≥95%, from Capsicum sp.

InChI key

YKPUWZUDDOIDPM-SOFGYWHQSA-N

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+

SMILES string

COc1cc(CNC(=O)CCCC\C=C\C(C)C)ccc1O

biological source

Capsicum sp.

assay

≥95%

mp

62-65 °C (lit.)

solubility

H2O: insoluble
ethanol: soluble

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... CYP1A2(1544), TRPV1(7442)
rat ... Trpv1(83810), Trpv4(66026)

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Catégories apparentées

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.

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.

signalword

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

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
WXBF8180V
WXBF7571V
WXBF6110V
WXBF5353V
WXBF4163V

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    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

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Stimulation of TRPV1 channels activates the AP-1 transcription factor.
Backes TM, et al.
Biochemical Pharmacology, 150(3), 160-169 (2018)
Chemical and Pharmacological Aspects of Capsaicin
Maria D, et al.
Molecules (Basel), 16(2), 1253-1270 (2011)
Surinder Kumar Sharma et al.
European journal of pharmacology, 720(1-3), 55-62 (2013-11-12)
Capsaicin is the active ingredient of chili peppers and gives them the characteristic pungent flavor. Understanding the actions of capsaicin led to the discovery of its receptor, transient receptor potential vanilloid subfamily member 1 (TRPV1). This receptor is found on
Ann M Bode et al.
Cancer research, 71(8), 2809-2814 (2011-04-14)
Capsaicin (trans-8-methyl-N-vanillyl-6-nonenamide) is the principal pungent component in hot peppers, including red chili peppers, jalapeños, and habaneros. Consumed worldwide, capsaicin has a long and convoluted history of controversy about whether its consumption or topical application is entirely safe. Conflicting epidemiologic
Capsaicin upregulates HDAC2 via TRPV1 and impairs neuronal maturation in mice.
Wang S, et al.
Experimental & Molecular Medicine, 50(3), e455-e455 (2018)
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Contenu apparenté

Product Information Sheet - M2028

Product Information Sheet

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