CIS-TRIMETHOXY STILBENE Property

Melting point:

55-57 °C

Boiling point:

423.8±35.0 °C(Predicted)

Density 

1.104±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

≤50mg/ml in DMSO;50mg/ml in dimethyl formamide

form 

solution in ethanol.

CAS DataBase Reference

94608-23-8

Safety

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

CIS-TRIMETHOXY STILBENE Chemical Properties,Usage,Production

Description

Resveratrol is a potent antioxidant found in grapes and red wine that also has anti-proliferative, anti-neoplastic and anti-angiogenic activities. In addition, resveratrol activates sirtuins and, in yeast, extends lifespan. cis-trismethoxy Resveratrol is a potent anti-mitotic drug that is 100-fold more active than resveratrol at inhibiting the growth of human colon cancer Caco-2 cells. It inhibits tubulin polymerization in a dose-dependent manner (IC₅₀ = 4 μM) and inhibits enzymes involved in the synthesis of the polyamines, putrescine, and spermidine. trans-trismethoxy Resveratrol has superior pharmacokinetic characteristics when compared with resveratrol, including greater plasma exposure, longer elimination half-life, and lower clearance.

Uses

Resveratrol is a potent antioxidant found in grapes and red wine that also has anti-proliferative, anti-neoplastic and anti-angiogenic activities. In addition, resveratrol activates sirtuins and, in yeast, extends lifespan. cis-trismethoxy Resveratrol is a potent anti-mitotic drug that is 100-fold more active than resveratrol at inhibiting the growth of human colon cancer Caco-2 cells. It inhibits tubulin polymerization in a dose-dependent manner (IC50 = 4 μM) and inhibits enzymes involved in the synthesis of the polyamines, putrescine, and spermidine. trans-trismethoxy Resveratrol has superior pharmacokinetic characteristics when compared with resveratrol, including greater plasma exposure, longer elimination half-life, and lower clearance.

Uses

cis-trismethoxy Resveratrol is a potent antioxidant found in grapes and red wine. Also, it is a resveratrol analog with increased antiproliferative activity towards a number of cancer cell lines.

in vitro

cis-trismethoxy resveratrol at 0.3 microm could exert a 80% growth inhibition of human colon cancer caco-2 cells and arrest growth completely at 0.4 microm. the cis conformation of cis-trismethoxy resveratrol was also 100-fold more potent than the trans isomer. cis-trismethoxy resveratrol was able to cause cell cycle arrest at the g2/m phase transition and inhibit tubulin polymerization dose-dependently, leading to the depletion of the polyamines, putrescine and spermidine. in addition, cis-trismethoxy resveratrol inhibited partially colchicine binding to its binding site on tubulin [1].

in vivo

previous study found that from the angle of pharmacokinetics, cis-trismethoxy resveratrol appeared to be a superior analog of resveratrol since it was orally available and showed greater plasma exposure, longer elimination half-life and lower clearance. due to the superior pharmacokinetic characteristics of cis-trismethoxy resveratrol had, its potentials as a preventive or therapeutic agent in resveratrol-effective diseases would be considered [2].

IC 50

4 microm for tubulin polymerization

References

[1] schneider, y. ,chabert, p.,stutzmann, j., et al. resveratrol analog (z)-3,5,4'-trimethoxystilbene is a potent anti-mitotic drug inhibiting tubulin polymerization. international journal of cancer 107, 189-196 (2003).
[2] lin, h. s. and ho, p.c. a rapid hplc method for the quantification of 3,5,4'-trimethoxy-trans-stilbene (tms) in rat plasma and its application in pharmacokinetic study. journal of pharmaceutical & biomedical analysis 49, 387-392 (2009).