Trimethoxystilbene

Names

[ Name ]:
Trimethoxystilbene

[Synonym ]:
Trimethoxy-trans-stilbene
3,4',5-Trimethoxy-trans-stilbene
trimethoxy-trans-resveratrol
1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
TRISMETHOXYRESVERATROL
resverarol trimethyl ether
1,3-Dimethoxy-5-[(E)-2-(4-methoxyphenyl)vinyl]benzene
1,3-dimethoxy-5-[(1E)-2-(4-methoxyphenyl)ethenyl]-benzene
methylated trans-resveratrol
(E)-1,3-Dimethoxy-5-(4-methoxystyryl)benzene
3,5,4'-Trimethoxystilbene
E-Resveratrol Trimethyl Ether
Resveratrol trimethyl ether
Benzene, 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]-
3,4',5-trimethoxystilbene
Tri-O-methylresveratrol
3,5,4'-TRIMETHOXY-TRANS-STILBENE
1,3-Dimethoxy-5-[(E)-2-(4-methoxy-phenyl)-vinyl]-benzene
O-permethylated E-resveratrol
trans-Trimethoxyresveratrol

Biological Activity

[Description]:

Trans-Trimethoxyresveratrol is a derivative of Resveratrol (RSV),and it may be a more potent anti-inflammatory, antiangiogenic and vascular-disrupting agent when compared with resveratrol.In vitro: The in vitro study of resveratrol and trans-Trimethoxyresveratrol showed rather weak cytotoxic effects on three cancer cell lines (HepG2, MCF-7, and MDA-MB-231), which contradicted a previous study reporting that resveratrol inhibited MCF-7 cells with an IC50 of about 10?μM. This discrepancy might be explained by the fact that the measurements were made 24?h after drug treatment, whereas the measurements of the previous study were taken 6 days after. The fact that the cytotoxic effect of trans-Trimethoxyresveratrol was lower than that of resveratrol is surprising, because in many studies, trans-Trimethoxyresveratrol is the most active analogue of resveratrol , although resveratrol shows much stronger antioxidant effects than that of trans-Trimethoxyresveratrol.[1]In vivo: Zebrafish embryos offer great advantage over their adults as well as other in vivo models because of the external development and optical transparency during their first few days, making them invaluable in the inspection of developmental processes. These unique advantages can even be made more useful when specific cell types are labeled with fluorescent probes. Zebrafish embryo in vivo, suggests that trans-Trimethoxyresveratrol has both more potent antiangiogenic activity and more importantly, stronger specific cytotoxic effects on endothelial cells than does resveratrol.[1]

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[References]

[1]. Alex, D. et al. Resveratrol derivative, trans-3,5,4'-trimethoxystilbene, exerts antiangiogenic and vascular-disrupting effects in zebrafish through the downregulation of VEGFR2 and cell-cycle modulation. Journal of cellular biochemistry 109, 339-346, doi:

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
423.8±35.0 °C at 760 mmHg

[ Melting Point ]:
57ºC

[ Molecular Formula ]:
C₁₇H₁₈O₃

[ Molecular Weight ]:
270.323

[ Flash Point ]:
144.4±23.2 °C

[ Exact Mass ]:
270.125580

[ PSA ]:
27.69000

[ LogP ]:
4.61

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.600

[ Storage condition ]:
?20°C

[ Water Solubility ]:
DMSO: ≥34mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS05, GHS07, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H318-H335-H410

[ Precautionary Statements ]:
P261-P273-P280-P305 + P351 + P338-P501

[ Hazard Codes ]:
Xi,N

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36/37/39

[ RIDADR ]:
UN 3077 9 / PGIII

[ HS Code ]:
2909309090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Preparation

Customs

[ HS Code ]: 2909309090

[ Summary ]:
2909309090 other aromatic ethers and their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

Resveratrol analog-3,5,4'-trimethoxy-trans-stilbene inhibits invasion of human lung adenocarcinoma cells by suppressing the MAPK pathway and decreasing matrix metalloproteinase-2 expression.

Mol. Nutr. Food. Res. 53(3) , 407-16, (2009)

Resveratrol (3,5,4'-trihydroxystilbene) is a natural polyphenol that presents various physiological activities. It has been reported that the methylated derivatives of resveratrol show better potentia...

Trans- and cis-stilbene polyphenols induced rapid perinuclear mitochondrial clustering and p53-independent apoptosis in cancer cells but not normal cells.

Eur. J. Pharmacol. 587 , 25-34, (2008)

We previously reported that 3,4,5,4'-tetramethoxy-trans-stilbene (MR-4) induces p53 and perinuclear mitochondrial clustering in cancer cells [Gosslau, A., Chen, M., Ho, C.-T., Chen, K.Y., 2005, A meth...