P0453

Piceatannol

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
• Empirical Formula (Hill Notation): C₁₄H₁₂O₄
• CAS Number: 10083-24-6
• Molecular Weight: 244.24
• MDL number: MFCD00221715
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278620
• NACRES: NA.77

Properties

• 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)

Description

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302 + H312 + H332
• Precautionary Statements: 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 Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves