PICEATANNOL

Synonym(s):(E)-4-[2-(3,5Dihydroxyphenyl)ethenyl]1,2-benzenediol;trans-3,3?,4,5?-Tetrahydroxystilbene;3,3′,4,5′-Stilbenetetrol;3,3′,4,5′-Tetrahydroxy-trans-stilbene;Astringenin

CAS NO.：10083-24-6
Empirical Formula: C14H12O4
Molecular Weight: 244.24
MDL number: MFCD00221715
EINECS: 600-132-4
SAFETY DATA SHEET (SDS)
Update Date: 2025-12-25 11:31:46

What is PICEATANNOL?

Description

Piceatannol (10083-24-6) is a naturally occurring analog of resveratrol (Cat.# 10-1057). Inhibits nonreceptor kinases Syk and Lyk (IC50 approximately 10 μM).1 Piceatannol stimulates Sirt1.2

Chemical properties

yellow to golden or green crystalline powder

The Uses of PICEATANNOL

A human metabolite of Resveratrol (R150000). Piceatannol is strong anti-oxidant.

The Uses of PICEATANNOL

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)

What are the applications of Application

Piceatannol is an inhibitor of Syk and NF-κB activation

Definition

ChEBI: A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.

General Description

A cell-permeable, substrate competitive and reversible plant metabolite that inhibits the activity of rat liver protein kinase A catalytic subunit (IC₅₀ = 3 μM), PKC (IC₅₀ = 8 μM), MLCK (IC₅₀ = 12 μM). In RBL-2H3 cells, the selective inhibition of Syk by piceatannol results in inhibition of FceR1-mediated signaling. Also inhibits wheat embryo Ca²⁺-dependent protein kinase (CDPK) (IC₅₀ = 19 μM), and p72^syk (IC₅₀ = 10 μM), a non-receptor tyrosine kinase, relative to Lyn in isolated enzyme preparations. Also possesses anti-leukemic properties. Reported to activate sirtuins and promote the survival of eukaryotic cells.

Biological Activity

Anti-inflammatory, immunomodulatory and antiproliferative agent. Inhibits p56 lck and syk protein tyrosine kinases and inhibits TNF-induced NF- κ B activation and gene expression. Synthesis results from conversion of resveratrol (5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3,benzenediol ) by cytochrome P450 1B1.

Biochem/physiol Actions

Cell permeable: yes

Storage

+4°C

References

1) Seow et al. (2002), Piceatannol, a Syk-selective tyrosine kinase inhibitor, attenuated antigen challenge of guinea pig airways in vitro; Eur. J. Pharmacol., 443 189 2) Howitz et al. (2003), Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan; Nature, 425 191

Properties of PICEATANNOL

Melting point:	223.0-227.0 °C
Boiling point:	108°C/0.04mmHg(lit.)
Density	1.1245 (rough estimate)
refractive index	1.5190 (estimate)
storage temp.	2-8°C
solubility	H₂O: 0.5 mg/mL
form	powder
pka	9.17±0.10(Predicted)
color	light tan to yellow
λmax	323nm(MeOH)(lit.)
Stability:	Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.

Safety information for PICEATANNOL

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.