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94608-23-8

94608-23-8 Structure

94608-23-8 Structure
IdentificationBack Directory
[Name]

CIS-TRIMETHOXY STILBENE
[CAS]

94608-23-8
[Synonyms]

CIS-TRIMETHOXY STILBENE
CIS-TRISMETHOXY RESVERATROL
(Z)-3,5,4'-Trimethoxystilbene
CIS-TRIMETHOXY STILBENE USP/EP/BP
Resveratrol Trimethyl Ether cis-Isomer
1,2,3-trimethoxy-4-(2-phenylethenyl)benzene
Resveratrol Impurity 27 (cis-trismethoxy Resveratrol)
(Z)-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethene
1,3-dimethoxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]benzene
1,3-DIMETHOXY-5-[(1Z)-2-(4-METHOXYPHENYL)ETHENYL]-BENZENE
Benzene, 1,3-dimethoxy-5-[(1Z)-2-(4-methoxyphenyl)ethenyl]-
[Molecular Formula]

C17H18O3
[MDL Number]

MFCD11977725
[MOL File]

94608-23-8.mol
[Molecular Weight]

270.326
Chemical PropertiesBack Directory
[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 DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

41
[Safety Statements ]

26-39
Hazard InformationBack Directory
[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.
[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
[storage]

Store at -20°C
[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).
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