4-(2-(3,5-Dihydroxyphenyl)-ethenyl)-1,2-benzoldiol

Bezeichnung:4-(2-(3,5-Dihydroxyphenyl)-ethenyl)-1,2-benzoldiol

CAS-Nr10083-24-6

Englisch Name:PICEATANNOL

CBNumberCB8377487

SummenformelC14H12O4

Molgewicht244.24

MOL-Datei10083-24-6.mol

Synonyma

4-(2-(3,5-Dihydroxyphenyl)-ethenyl)-1,2-benzoldiol

4-(2-(3,5-Dihydroxyphenyl)-ethenyl)-1,2-benzoldiol physikalisch-chemischer Eigenschaften

Schmelzpunkt	223.0-227.0 °C
Siedepunkt	108°C/0.04mmHg(lit.)
Dichte	1.1245 (rough estimate)
Brechungsindex	1.5190 (estimate)
storage temp.	2-8°C
Löslichkeit	H₂O: 0.5 mg/mL
Aggregatzustand	powder
pka	9.17±0.10(Predicted)
Farbe	light tan to yellow
maximale Wellenlänge (λmax)	323nm(MeOH)(lit.)
Stabilität	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)

Sicherheit

S-Sätze:	24/25
WGK Germany	3
HS Code	29072990

Gefahreninformationscode (GHS)

PICEATANNOL Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
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
Chemische Eigenschaften
yellow to golden or green crystalline powder
Verwenden
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)
Verwenden
A human metabolite of Resveratrol (R150000). Piceatannol is strong anti-oxidant.
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.
Allgemeine Beschreibung
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.
Biologische Aktivität
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
Lager
+4°C
Einzelnachweise
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

PICEATANNOL Upstream-Materialien And Downstream Produkte

4-(2-(3,5-Dihydroxyphenyl)-ethenyl)-1,2-benzoldiol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

10083-24-6, PICEATANNOL Verwandte Suche:

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