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Merck

12084

Capsaicin

analytical standard

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:
404-86-4
Peso molecular:
305.41
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329749614
EC Number:
206-969-8
Beilstein/REAXYS Number:
2816484
MDL number:
MFCD00017259

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Nombre del producto

Capsaicin, analytical standard

Quality Level

100

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

InChI key

YKPUWZUDDOIDPM-SOFGYWHQSA-N

grade

analytical standard

description

analytical standard for food analysis

assay

≥98.5% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

62-65 °C (lit.)

solubility

H2O: insoluble

application(s)

cleaning products
cosmetics
flavors and fragrances
food and beverages
forensics and toxicology
personal care
pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

Gene Information

human ... TRPV1(7442)

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Categorías relacionadas

Application

This analytical standard was used as follows:
  • Determination of capsaicin in samples of chili pepper, black pepper powder, and chili pepper sauce by cyclic voltammetry using an office paper-based carbon black-screen printed electrode (CB-SPE)
  • Development of an electrochemical sensor based on Ag/Ag2O-loaded poly(sodium-4-styrenesulfonate) (PSS) functionalized-reduced graphene oxide (rGO) composite (Ag/Ag2O-PSS-Rgo) to determine capsaicin in chili pepper samples
  • Multi-residue analysis of six capsaicinoids in green bell pepper samples using an online supercritical fluid extraction combined with reverse phase-liquid chromatography-tandem mass spectrometry (RP-LC-MS/MS)
  • Evaluation of an immunoaffinity chromatography (IAC) based cleanup using polyclonal antibodies (pAb) for the determination of capsaicin and dihydrocapsaicin in different types of vegetable oil samples by LC-MS/MS
  • Thin layer chromatographic (TLC) separation and determination of capsaicin in ethanolic extracts of Capsicum annum Linn

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.

Features and Benefits

Superior quality of pure E-Capsaicin, with a guaranteed assay of =99.0% by HPLC.

Other Notes

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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

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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Certificados de análisis (COA)

Lot/Batch Number
BCCH6691
BCCD1287
BCCC0162
BCBZ3842
BCBS7557V

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Study of capsaicin content in various parts of pepper fruit by liquid chromatography with electrochemical detection.
Supalkova, Veronika, et al.
Acta Chimica Slovenica, 54.1, 55-55 (2007)
S W Hwang et al.
Proceedings of the National Academy of Sciences of the United States of America, 97(11), 6155-6160 (2000-05-24)
Capsaicin, a pungent ingredient of hot peppers, causes excitation of small sensory neurons, and thereby produces severe pain. A nonselective cation channel activated by capsaicin has been identified in sensory neurons and a cDNA encoding the channel has been cloned
Zohar Bromberg et al.
PloS one, 8(2), e57149-e57149 (2013-03-08)
The heat shock response (HSR) is a highly conserved molecular response to various types of stresses, including heat shock, during which heat-shock proteins (Hsps) are produced to prevent and repair damages in labile proteins and membranes. In cells, protein unfolding
Jennifer Leech et al.
American journal of respiratory and critical care medicine, 188(9), 1069-1075 (2013-10-08)
Antitussive therapies are accompanied by a substantial placebo effect, indicating that inhibitory circuits in the brain have a significant capacity to regulate cough neural processing. However, essentially nothing is known about the identity of these inhibitory circuits or how they
Helen Sumner et al.
American journal of respiratory and critical care medicine, 187(9), 943-949 (2013-03-09)
Cough is one of the principal symptoms of chronic obstructive pulmonary disease (COPD) but the potential drivers of cough are likely to be multifactorial and poorly understood. To quantify cough frequency in an unselected group of subjects with COPD and
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