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,[1] that is extracted from grapes, red wine and Euphorbia lagascae seeds.[2]

Application

Piceatannol has been used:

• to study its effect on Ataxia-Telangiectasia Mutated (ATM) protein kinase[3]
• as an inhibitor of ZAP-70 (ζ-chain-associated protein kinase 70)[4]
• 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)[5]

Biochem/physiol Actions

Piceatannol is an analog of resveratrol that possess potential anti-oxidant,[3] anti-cancer and anti-inflammatory properties. Picetannol has been shown to interfere with the cytokine signaling pathway,[1] notably in the inhibition of the spleen tyrosine kinase (Syk) and PI3K.[2] 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.[1]

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