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P0453

Sigma-Aldrich

Piceatannol

powder

Sinónimos:

(E)-4-[2-(3,5Dihydroxyphenyl)ethenyl]1,2-benzenediol, 3,3′,4,5′-Stilbenetetrol, 3,3′,4,5′-Tetrahydroxy-trans-stilbene, Astringenin

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About This Item

Fórmula empírica (notación de Hill):
C14H12O4
Número de CAS:
10083-24-6
Peso molecular:
244.24
MDL number:
MFCD00221715
UNSPSC Code:
12352200
PubChem Substance ID:
24278620
NACRES:
NA.77

assay

≥98% (HPLC)

Quality Level

200

form

powder

color

light tan to yellow

mp

223.0-227.0 °C

solubility

H2O: 0.5 mg/mL
DMSO: 10 mg/mL
ethanol: 10 mg/mL

storage temp.

2-8°C

SMILES string

Oc1cc(O)cc(\C=C\c2ccc(O)c(O)c2)c1

InChI

1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+

InChI key

CDRPUGZCRXZLFL-OWOJBTEDSA-N

Gene Information

human ... CDK2(1017)

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General description

Piceatannol is a natural tetrahydroxystilbene, that is extracted from grapes, red wine and Euphorbia lagascae seeds.

Application

Piceatannol has been used:
  • to study its effect on Ataxia-Telangiectasia Mutated (ATM) protein kinase
  • as an inhibitor of ZAP-70 (ζ-chain-associated protein kinase 70)
  • as an inhibitor of MRP1-mediated 2′,7′-bis-(carboxypropyl)-5(6)-carboxyfluorescein (BCPCF) transport in intact human erythrocytes and inside-out erythrocyte vesicles (IOVs)

Biochem/physiol Actions

Piceatannol is an analog of resveratrol that possess potential anti-oxidant, anti-cancer and anti-inflammatory properties. Picetannol has been shown to interfere with the cytokine signaling pathway, notably in the inhibition of the spleen tyrosine kinase (Syk) and PI3K. It also inhibits the activation of NFκB in human cultured cells, after treatment with several inflammatory agents, through inhibition of IκBα kinase and p65 phosphorylation.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Physical form

Photosensitive powder

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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José Pedro Lopes et al.
Frontiers in cellular and infection microbiology, 9, 289-289 (2019-08-29)
Cryptococcosis, caused by the basidiomycete Cryptococcus neoformans, is a life-threatening disease affecting approximately one million people per year worldwide. Infection can occur when C. neoformans cells are inhaled by immunocompromised people. In order to establish infection, the yeast must bypass
Piceatannol, natural polyphenolic stilbene, inhibits adipogenesis via modulation of mitotic clonal expansion and insulin receptor-dependent insulin signaling in early phase of differentiation
Kwon JY, et al.
The Journal of Biological Chemistry, 287(14), 11566-11578 (2012)
Nelly Noraz et al.
Development (Cambridge, England), 143(12), 2183-2193 (2016-04-29)
In the hematopoietic system, Syk family tyrosine kinases are essential components of immunoreceptor ITAM-based signaling. While there is increasing data indicating the involvement of immunoreceptors in neural functions, the contribution of Syk kinases remains obscure. Previously, we identified phosphorylated forms
Piceatannol inhibits TNF-induced NF-$\kappa$B activation and NF-$\kappa$B-mediated gene expression through suppression of I$\kappa$B$\alpha$ kinase and p65 phosphorylation
Ashikawa K, et al.
Journal of immunology (Baltimore, Md. : 1950), 169(11), 6490-6497 (2002)
A candidate anti-HIV reservoir compound, auranofin, exerts a selective `anti-memory?effect by exploiting the baseline oxidative status of lymphocytes
Chirullo B, et al.
Cell Death & Disease, 4(12), e944-e944 (2013)
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