3,4',5-TRIMETHOXY-TRANS-STILBENE Chemical Properties

Melting point:

57°C

Boiling point:

423.8±35.0 °C(Predicted)

Density 

1.104±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO: ≥34mg/mL

form 

powder to crystal

color 

white to tan

InChI

InChI=1S/C17H18O3/c1-18-15-8-6-13(7-9-15)4-5-14-10-16(19-2)12-17(11-14)20-3/h4-12H,1-3H3/b5-4+

InChIKey

GDHNBPHYVRHYCC-SNAWJCMRSA-N

SMILES

C1(OC)=CC(/C=C/C2=CC=C(OC)C=C2)=CC(OC)=C1

CAS DataBase Reference

22255-22-7

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50/53-41-37/38

Safety Statements 

26-36/37/39-61-60-39

RIDADR 

UN 3077 9 / PGIII

HS Code 

2909.30.6000

3,4',5-TRIMETHOXY-TRANS-STILBENE Usage And Synthesis

Description

trans-trismethoxy Resveratrol is a polyketide synthase-derived stilbene originally isolated from Virola cuspidata that has diverse biological activities. It is cytotoxic to several cancer cell lines, including PC3, KB, HT-29, SW480, and HL-60 cells (IC₅₀s =3.6, 10.2, 16.1, 54, and 2.5 μM, respectively). trans-trismethoxy Resveratrol (15 μM) inhibits TNF-α-induced activation of NF-κB in HEK293T cells in a reporter assay. It inhibits angiogenesis in zebrafish embryos when used at a concentration of 0.1 μM.

Chemical Properties

Pale Yellow Oil

Uses

A resveratrol analog with a variety of pharmacology action, including anti-cancer properties, anti-allergic activity, estrogenic activity, antiangiogenic activity, and vascular-targeting activity against microtubule-destabilization

Uses

A resveratrol analog with a variety of pharmacology action, including inst microtubule-destabilization

Uses

Phenolic compounds, particularly flavonoids, from plant sources have long been observed to have antioxidant activity with potential benefits for human health. Resveratrol is a potent phenolic antioxidant found in grapes and red wine that also has antiproliferative and anti-inflammatory activity. When the three phenolic hydroxyl groups of resveratrol are converted to methyl ethers, the inhibition of cell growth and pro-apoptotic activities of resveratrol are enhanced.

References

[1] MICHAEL B. AUSTIN  Joseph P N. The Chalcone Synthase Superfamily of Type III Polyketide Synthases[J]. ChemInform, 2003, 34 17. DOI: 10.1002/chin.200317284
[2] FAHAD S ALDAWSARI  Carlos A V M. 3,4’,5-trans-Trimethoxystilbene; a natural analogue of resveratrol with enhanced anticancer potency.[J]. Investigational New Drugs, 2015, 33 3: 775-786. DOI: 10.1007/s10637-015-0222-x
[3] JUSTIN J. HEYNEKAMP. Substituted trans-Stilbenes, Including Analogues of the Natural Product Resveratrol, Inhibit the Human Tumor Necrosis Factor Alpha-Induced Activation of Transcription Factor Nuclear Factor KappaB[J]. Journal of Medicinal Chemistry, 2006, 49 24: 7182-7189. DOI: 10.1021/jm060630x
[4] MIRELLA BELLERI. Antiangiogenic and vascular-targeting activity of the microtubule-destabilizing trans-resveratrol derivative 3,5,4’-trimethoxystilbene.[J]. Molecular Pharmacology, 2005, 67 5: 1451-1459. DOI: 10.1124/mol.104.009043

3,4',5-TRIMETHOXY-TRANS-STILBENE(22255-22-7)Related Product Information

• Resveratrol
• trans Resveratrol 3-O-β-D-Glucuronide
• Resveratrol-3-4'-Disulfate
• Paclitaxel
• ISOLIQUIRITIN
• Chlorogenic acid
• 3-deoxysappanchalcone
• Costunolide
• Saikosaponin a
• alpha-(3,4-dihydroxyphenyl)lactic acid
• Dihydroresveratrol
• CIS-TRIMETHOXY STILBENE
• Oxyresveratrol
• trans/cis Resveratrol-D4
• Azo-Resveratrol
• cis Resveratrol
• trans Resveratrol 4O-b-D-Glucuronide
• trans Resveratrol-3,5-disulfate