| Identification | Back 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 Properties | Back 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. | [color ]
Colorless to light yellow | [CAS DataBase Reference]
94608-23-8 |
| Hazard Information | Back 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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