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HomeProduct name listAcetyl-trans-resveratrol

Acetyl-trans-resveratrol

Synonym(s):trans-3,5,4ʹ-Triacetylstilbene, 3,5,4ʹ-Tri-O-acetylresveratrol;Resveratrol, Triacetyl - CAS 42206-94-0 - Calbiochem

  • CAS NO.:42206-94-0
  • Empirical Formula: C20H18O6
  • Molecular Weight: 354.35
  • MDL number: MFCD01546481
  • EINECS: 695-560-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-02 19:02:54
Acetyl-trans-resveratrol Structural

What is Acetyl-trans-resveratrol?

Description

Triacetyl resveratrol (CAS 42206-94-0) is a resveratrol prodrug. One method for increasing the half-life of resveratrol?in vivo?is acetylation of the phenolic OH groups. Deacetylation takes place?in vivo?or in intact cells via the action of intracellular esterases releasing active resveratrol.

Chemical properties

White crystal or white crystal

The Uses of Acetyl-trans-resveratrol

trans-Resveratrol Triacetate is the acetylated analogue of Resveratrol (R150000) that is a natural antioxidant and a potential radioprotective agent. trans-Resveratrol Triacetate induces p53 activity and inhibits proliferation in breast and prostate tumor cell lines.

The Uses of Acetyl-trans-resveratrol

trans-Resveratrol Triacetate is the acetylated analogue of Resveratrol (R150000) that is a natural antioxidant and a potential radioprotective agent. trans-Resveratrol Triacetate induces p53 activity and inhibits proliferation in breast and prostate tumor cell lines.

What are the applications of Application

Triacetylresveratrol is a resveratrol precursor and SIRT activator

Definition

ChEBI: Acetic acid [4-[2-(3,5-diacetyloxyphenyl)ethenyl]phenyl] ester is a stilbenoid.

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 T1/2 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).

Biochem/physiol Actions

Triacetyl resveratrol displays superior bioavailability to the parent compound, resveratrol. The compound induces p53 activity and inhibits proliferation in breast and prostate tumor cell lines.

Mechanism of action

After acetylated resveratrol enters the body, it is converted into resveratrol in the body to exert its biological activity. Acetylated Resveratrol Compared to Regular Resveratrol:
1) The stability is enhanced. Since the three active phenolic hydroxyl groups are acetylated, the stability of acetylated resveratrol is significantly improved;
2) The bioavailability is improved, due to prolonging the residence time in the body and increasing the half-life, the bioavailability is better. Acetylated resveratrol can be widely used in food, beverage and health care products.

in vitro

Triacetylresveratrol significantly down-regulates anti-apoptotic Bcl-2 family protein Mcl-1 and up-regulates pro-apoptotic Bcl-2 family proteins Bim and Puma. Triacetylresveratrol inhibits cell viability, and induces apoptosis of pancreatic cancer cells in a concentration and incubation time-dependent manner.

References

1) Hsieh?et al.?(2011),?Control of prostate cell growth, DNA damage and repair and gene expression by resveratrol analogues, in vitro; Carcinogenesis,?32?93 2) Hsieh?et al.?(2011),?Regulation of p53 and cell proliferation by resveratrol and it’s derivatives in breast cancer cells: an in silico and biochemical approach to targeting integrin αvβ3; Int. J. Cancer,?129?2732

Properties of Acetyl-trans-resveratrol

Melting point: 117.0 to 121.0 °C
Boiling point: 504.8±50.0 °C(Predicted)
Density  1.241±0.06 g/cm3(Predicted)
storage temp.  room temp
solubility  DMSO: ≥18mg/mL
form  White powder
color  white to tan
Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

Safety information for Acetyl-trans-resveratrol

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
ghs
Environment
GHS09
GHS Hazard Statements H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H318:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H400:Hazardous to the aquatic environment, acute hazard
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Acetyl-trans-resveratrol

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