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P0453

Sigma-Aldrich

Piceatannol

powder

Synonyme(s) :

(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

Formule empirique (notation de Hill):
C14H12O4
Numéro CAS:
10083-24-6
Poids moléculaire :
244.24
Numéro MDL:
MFCD00221715
Code UNSPSC :
12352200
ID de substance PubChem :
24278620
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Niveau de qualité

200

Forme

powder

Couleur

light tan to yellow

Pf

223.0-227.0 °C

Solubilité

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

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

CDRPUGZCRXZLFL-OWOJBTEDSA-N

Informations sur le gène

human ... CDK2(1017)

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Description générale

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)

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Forme physique

Photosensitive powder

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 + H312 + H332

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

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, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "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
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)
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)
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