ChemicalBook CAS DataBase List 10083-24-6

10083-24-6

Name	PICEATANNOL
CAS	10083-24-6
EINECS(EC#)	600-132-4
Molecular Formula	C14H12O4
MDL Number	MFCD00221715
Molecular Weight	244.24
MOL File	10083-24-6.mol

Synonyms

Piceatanl Astringenin PICEATANNOL Piceatannol,96% (E)-Piceatannol trans-Piceatannol Piceatannol, (E)- (E)-3,3',4,5'-Stilbenetetrol 3,3',4,5'-TETRAHYDROXYSTILBENE (E)-3,3',4,5'-Tetrahydroxystilbene TRANS-3,3',4,5'-TETRAHYDROXYSTILBENE 3,3',4,5'-TETRAHYDROXY-TRANS-STILBENE 3,4,3',5'-TETRAHYDROXY-TRANS-STILBENE PICEATANNOL (3,3',4,5'-TETRAHYDROXY-TRAN (E)-4-(3,5-dihydroxystyryl)benzene-1,2-diol Piceatannol3,4,3',5'-Tetrahydroxy-trans-stilbene 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol (e)-4-[2-(3,5dihydroxyphenyl)ethenyl]1,2-benzenediol 5-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]benzene-1,3-diol 4-[(1E)-2-(3,5-DIHYDROXYPHENYL)ETHENYL]-1,2-BENZENEDIOL

Chemical Properties

Appearance	yellow to golden or green crystalline powder
Melting point	223-227 °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.
LogP	2.690 (est)

Safety Data

Safety Statements	24/25 less more
WGK Germany	3
HS Code	29072990

Hazard Information

Chemical Properties

yellow to golden or green crystalline powder

Uses

A human metabolite of Resveratrol (R150000).

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.

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.

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.

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

Questions And Answer

Spectrum Detail

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BioBioPha Co., Ltd.

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10083-24-6

Chemical Properties

Safety Data

Hazard Information

Chemical Properties

Uses

Definition

Biological Activity

General Description

Biochem/physiol Actions

storage

References

Questions And Answer

Description

Application

Spectrum Detail

Supplier

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