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(s): Resveratrol, Triacetyl, trans-3,5,4ʹ-Triacetylstilbene, 3,5,4ʹ-Tri-O-acetylresveratrol
• Empirical Formula (Hill Notation): C₂₀H₁₈O₈
• CAS Number: 42206-94-0
• Molecular Weight: 386.35
• MDL number: MFCD01546481
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥97% (HPLC)
• form: powder
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: 50 mg/mL
• shipped in: ambient
• storage temp.: 2-8°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+
• InChI key: PDAYUJSOJIMKIS-SNAWJCMRSA-N

Description

General description

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).

Packaging

Packaged under inert gas

Warning

Toxicity: Regulatory Review (Z)

Reconstitution

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

Other Notes

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

Legal Information

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3