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R8756

Sigma-Aldrich

Resiniferatoxin

from Euphorbia poisonii, ~95%

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About This Item

Formule empirique (notation de Hill):
C37H40O9
Numéro CAS:
57444-62-9
Poids moléculaire :
628.71
Numéro Beilstein :
5371150
Numéro MDL:
MFCD00135927
Code UNSPSC :
12352200
ID de substance PubChem :
24899411

Source biologique

Euphorbia poisonii

Niveau de qualité

100

Pureté

~95%

Température de stockage

−20°C

Chaîne SMILES 

[H][C@@]12C=C(C)C(=O)[C@@]1(O)CC(COC(=O)Cc3cc(O)cc(OC)c3)=CC4[C@H]5O[C@]7(Cc6ccccc6)O[C@]5(C[C@@H](C)[C@]24O7)C(C)=C

InChI

1S/C37H40O9/c1-21(2)35-17-23(4)37-29(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)11-22(3)32(34)40)20-43-31(39)15-25-12-27(38)16-28(13-25)42-5/h6-14,16,23,29-30,33,38,41H,1,15,17-20H2,2-5H3/t23-,29?,30-,33-,34-,35-,36-,37-/m1/s1

Clé InChI

IKYCZSUNGFRBJS-PMIKMUNESA-N

Informations sur le gène

rat ... Trpv1(83810)

Application

Resiniferatoxin has been used as an agonist to transient receptor potential vanilloid 2 (TRPV2):
  • for complex preparation for cryo-electron microscopy structural studies
  • to test its effect towards immune responses to P. aeruginosa in sensory neurons associated with the cornea
  • to study its effects in the denervation of the peripheral sensory nerves in psoriatic mice

Actions biochimiques/physiologiques

Potent VR1 vanilloid receptor agonist that has been used to label the vanilloid receptor in sensory ganglia; activates protein kinase C. Diterpene ester that is related to phorbol, but is not tumorigenic.
Resiniferatoxin (RTX) is an analog of capsaicin. It effectively ablates corneal sensory neurons by activating transient receptor potential vanilloid 1 (TRPV1) channels. RTX facilitates corneal bacterial clearance. It also elicits protective functionality towards cardiac function in a rat model with congestive heart failure (CHF).

Pictogrammes

Skull and crossbonesCorrosion
GHS06,GHS05

Mention d'avertissement

Danger

Mentions de danger

H301,H314

Classification des risques

Acute Tox. 3 Oral - Skin Corr. 1A

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Sigma-Aldrich

R8758

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J Szolcsanyi et al.
The Journal of pharmacology and experimental therapeutics, 255(2), 923-928 (1990-11-01)
Resiniferatoxin (RTX) has been shown to function as an ultrapotent analog of capsaicin. It is reported here that RTX, like capsaicin, acts selectively on primary sensory neurons in rats to produce ultrastructural alterations and calcitonin gene-related peptide depletion. To evaluate
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Tiffany Lin et al.
PLoS pathogens, 17(5), e1009557-e1009557 (2021-05-07)
We report a rapid reduction in blink reflexes during in vivo ocular Pseudomonas aeruginosa infection, which is commonly attributed and indicative of functional neuronal damage. Sensory neurons derived in vitro from trigeminal ganglia (TG) were able to directly respond to
Lejla Zubcevic et al.
eLife, 8 (2019-05-16)
The Transient Receptor Potential Vanilloid 2 (TRPV2) channel is a member of the temperature-sensing thermoTRPV family. Recent advances in cryo-electronmicroscopy (cryo-EM) and X-ray crystallography have provided many important insights into the gating mechanisms of thermoTRPV channels. Interestingly, crystallographic studies of
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