554328

Resveratrol, Triacetyl

A cell-permeable triacetate resveratrol prodrug that is easily converted to resveratrol by esterase activity and exhibits similar bioactivity as resveratrol in cell cultures.

• Synonym(e): Resveratrol, Triacetyl, trans-3,5,4ʹ-Triacetylstilbene, 3,5,4ʹ-Tri-O-acetylresveratrol
• Empirische Formel (Hill-System): C₂₀H₁₈O₈
• CAS-Nummer: 42206-94-0
• Molekulargewicht: 386.35
• MDL-Nummer: MFCD01546481
• UNSPSC-Code: 12352200
• NACRES: NA.77

Eigenschaften

• Qualitätsniveau: 100
• Assay: ≥97% (HPLC)
• Form: powder
• Hersteller/Markenname: Calbiochem^®
• Lagerbedingungen: OK to freeze; protect from light
• Farbe: white
• Löslichkeit: DMSO: 50 mg/mL
• Versandbedingung: ambient
• Lagertemp.: 2-8°C
• SMILES String: O(c1cc(cc(c1)\C=C\c2ccc(cc2)OC(=O)C)OC(=O)C)C(=O)C
• InChI: 1S/C20H18O6/c1-13(21)24-18-8-6-16(7-9-18)4-5-17-10-19(25-14(2)22)12-20(11-17)26-15(3)23/h4-12H,1-3H3/b5-4+
• InChIKey: PDAYUJSOJIMKIS-SNAWJCMRSA-N

Beschreibung

Allgemeine Beschreibung

A cell-permeable triacetate resveratrol prodrug that is easily converted to resveratrol by esterase activity and exhibits similar bioactivity as resveratrol in cell cultures. Cremophor EL is reported to protect the prodrug from fast hydrolysis and resveratrol conversion in mouse serum at 37°C (100% conversion within 20 sec vs. >300 min or T_1/2 of 48 min delivered with DMSO or 1:1:8 (v/v/v) EtOH/Cremophor EL/H₂O, respectively; [prodrug]_t=0 = 100 µM), although the active drug resveratrol is stable for more than 27 h under the same condition without Cremophor EL. When dosed at 10 mg/kg and delivered with 1:1:8 (v/v/v) EtOH/Cremophor EL/H₂O intraperitoneally before, but not after, exposure to lethal γ-irradiation (9.75 Gy), the prodrug, but not resveratrol, is shown to greatly prevent irradiation-induced death in mice in vivo (survival rate = 77.4% with 10 mg/kg prodrug vs. ≤28.3% with 10 mg/kg resveratrol, vehicle alone, or no pretreatment at all).

Verpackung

Packaged under inert gas

Warnhinweis

Toxicity: Regulatory Review (Z)

Rekonstituierung

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Sonstige Hinweise

Koide, K., et al. 2011. ACS Med. Chem. Lett.2, 270.
Hsieh, T.C., et al. 2011. Int. J. Cancer129, 2732.

Rechtliche Hinweise

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3