P0453

Piceatannol

Name: Piceatannol
Brand: SIGMA

≥98% (HPLC), Resveratrol analog, powder

Synonym(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

Empirical Formula (Hill Notation):

C₁₄H₁₂O₄

CAS Number:

10083-24-6

Molecular Weight:

244.24

UNSPSC Code:

12352200

PubChem Substance ID:

24278620

NACRES:

NA.77

MDL number:

MFCD00221715

Product Name

Piceatannol, powder

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

assay

≥98% (HPLC)

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

Quality Level

200

Gene Information

human ... CDK2(1017)

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

General description

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

Physical form

Photosensitive powder

pictograms

GHS07

signalword

Warning

hcodes

H302 + H312 + H332

pcodes

P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000453976

0000219282

0000215417

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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

Syk kinases are required for spinal commissural axon repulsion at the midline via the ephrin/Eph pathway.

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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