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M2028

Sigma-Aldrich

Capsaicin

≥95%, from Capsicum sp.

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Synonym(s):
8-Methyl-N-vanillyl-trans-6-nonenamide
Linear Formula:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
CAS Number:
Molecular Weight:
305.41
Beilstein/REAXYS Number:
2816484
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
21750PHR1450360376
Capsaicin ≥95%, from Capsicum sp.

M2028

Capsaicin

Capsaicin from Capsicum sp., ≥50% (HPLC)

21750

Capsaicin

Capsaicin Pharmaceutical Secondary Standard; Certified Reference Material

PHR1450

Capsaicin

Capsaicin natural

360376

Capsaicin

Quality Level

200

Quality Level

100

Quality Level

300

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

H2O: insoluble, ethanol: soluble

solubility

H2O: insoluble

solubility

-

solubility

chloroform: 5%

biological source

Capsicum sp.

biological source

Capsicum sp.

biological source

-

biological source

-

mp

62-65 °C (lit.)

mp

62-65 °C (lit.), 62-66 °C

mp

62-65 °C (lit.)

mp

62-65 °C (lit.)

Application

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.

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

Storage Class

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

wgk_germany

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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Nordihydrocapsaicin phyproof® Reference Substance

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Nordihydrocapsaicin

Dihydrocapsaicin United States Pharmacopeia (USP) Reference Standard

USP

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Capsiate analytical standard

Supelco

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Dihydrocapsaicin phyproof® Reference Substance

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Capsazepine A competitive antagonist of Capsaicin and resiniferatoxin. Capsazepine (1 µM) blocks capsaicin (60 nM) stimulated firing of C-fibers.

Sigma-Aldrich

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Capsazepine

Stimulation of TRPV1 channels activates the AP-1 transcription factor.
Backes TM, et al.
Biochemical Pharmacology, 150(3), 160-169 (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
Capsaicin upregulates HDAC2 via TRPV1 and impairs neuronal maturation in mice.
Wang S, et al.
Experimental & Molecular Medicine, 50(3), e455-e455 (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
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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