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Triacetyl Resveratrol

Catalog No.
B5971
Cell-permeable resveratrol prodrug
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$55.00
In stock
10mg
$50.00
In stock
25mg
$92.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

Tel: +1-832-696-8203

Email: [email protected]

Worldwide Distributors

Background

Triacetyl Resveratrol is a cell-permeable and more stable resveratrol prodrug [1].

Triacetyl Resveratrol is a potential and cell-permeable resveratrol prodrug. In 32D-cl3 cells, triacetyl resveratrol (3', 5',4'-Tri-O-acetylresveratrol) protected cells from irradiation and increased radioresistance, and is slightly more potent than resveratrol [1]. In lysates derived from HEK293-TYR cells, triacetyl resveratrol inhibited human TYR activity with IC50 value of 20 μM. In HEMs, triacetyl resveratrol was less cytotoxic than resveratrol. In both murine melanoma B16/F10 cells and HEMs, triacetyl resveratrol effectively inhibited intracellular melanin contents increased by α-MSH and L-tyrosine, respectively. Triacetyl Resveratrol was easily digested to resveratrol by esterases [2]. In LNCaP cells, triacetyl-resveratrol activated p53, increased p21 and p53R2 and decreased PSA expression. In CWR22Rv1 cells (mutated p53), triacetyl-resveratrol induced G1/S arrest [3]. In MCF-7 and MDA-MB-231 breast cancer cells, triacetyl-resveratrol interacted avidly and specifically with integrin αvβ3 through binding at the site targeted by the RGD peptide. Triacetyl-resveratrol induced ERK and p38 phosphorylation [4].

In γ-irradiated mice, 3,5,4'-Tri-O-acetylresveratrol (10 mg/kg) prior to γ-irradiation exhibited significant protective activity with 80% survival rate. Moreover, 3', 5',4'-Tri-O-acetylresveratrol had longer half-life that may assist more rapid distribution to tissues [1].

References:
[1].  Koide K, Osman S, Garner AL, et al. The Use of 3,5,4'-Tri-O-acetylresveratrol as a Potential Pro-drug for Resveratrol Protects Mice from γ-Irradiation-Induced Death. ACS Med Chem Lett, 2011, 2(4): 270-274.
[2].  Park J, Park JH, Suh HJ, et al. Effects of resveratrol, oxyresveratrol, and their acetylated derivatives on cellular melanogenesis. Arch Dermatol Res, 2014, 306(5): 475-487.
[3].  Hsieh TC, Huang YC, Wu JM. Control of prostate cell growth, DNA damage and repair and gene expression by resveratrol analogues, in vitro. Carcinogenesis, 2011, 32(1): 93-101.
[4].  Hsieh TC, Wong C, John Bennett D, et al. Regulation of p53 and cell proliferation by resveratrol and its derivatives in breast cancer cells: an in silico and biochemical approach targeting integrin αvβ3. Int J Cancer, 2011, 129(11): 2732-2743.

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt354.35
Cas No.42206-94-0
FormulaC20H18O6
Solubilityinsoluble in EtOH; insoluble in H2O; ≥13.85 mg/mL in DMSO
Chemical Name(E)-5-(4-acetoxystyryl)-1,3-phenylene diacetate
SDFDownload SDF
Canonical SMILESCC(OC1=CC=C(C=C1)/C([H])=C([H])/C2=CC(OC(C)=O)=CC(OC(C)=O)=C2)=O
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Quality Control

Chemical structure

Triacetyl Resveratrol