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P0453

Sigma-Aldrich

Piceatannol

powder

Sinonimo/i:

(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

Formula empirica (notazione di Hill):
C14H12O4
Numero CAS:
10083-24-6
Peso molecolare:
244.24
Numero MDL:
MFCD00221715
Codice UNSPSC:
12352200
ID PubChem:
24278620
NACRES:
NA.77

Saggio

≥98% (HPLC)

Livello qualitativo

200

Stato

powder

Colore

light tan to yellow

Punto di fusione

223.0-227.0 °C

Solubilità

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

Temperatura di conservazione

2-8°C

Stringa SMILE

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+
CDRPUGZCRXZLFL-OWOJBTEDSA-N

Informazioni sul gene

human ... CDK2(1017)

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Descrizione generale

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

Applicazioni

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)

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Stato fisico

Photosensitive powder

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302 + H312 + H332

Classi di pericolo

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
099M4010V
028M4015V
067M4127V
028M40115V
058M4015V

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Resveratrolo ≥99% (HPLC)

Sigma-Aldrich

R5010

Resveratrolo

BAY 61-3606 hydrochloride hydrate ≥98% (HPLC), powder

Sigma-Aldrich

B9685

BAY 61-3606 hydrochloride hydrate

Aspalathin primary reference standard

03520585

Aspalathin

Triacetyl resveratrol ≥98% (HPLC)

Sigma-Aldrich

SML0032

Triacetyl resveratrol

Polydatin United States Pharmacopeia (USP) Reference Standard

USP

1546194

Polydatin

Astragaloside IV >98.0%

Millipore

74777

Astragaloside IV

PP2 ≥98% (HPLC)

Sigma-Aldrich

P0042

PP2

Resveratrolo phyproof® Reference Substance

PHL89539

Resveratrolo

Galangin autophagy inducing flavonoid

Sigma-Aldrich

282200

Galangin

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, 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)
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
Resveratrol oligomers are potent MRP1 transport inhibitors
BOBROWSKA HM, et al.
Anticancer Research, 26(3A), 2081-2084 (2006)
Direct activation of ATM by resveratrol under oxidizing conditions
Lee JH, et al.
Testing, 9(6), e97969-e97969 (2014)
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