(E)-3,5,4'-Trimethoxystilbene

Base Information

• Chemical Name: (E)-3,5,4'-Trimethoxystilbene
• CAS No.: 22255-22-7
• Molecular Formula: C17H18O3
• Molecular Weight: 270.328
• Hs Code.: 2909309090
• European Community (EC) Number: 694-659-7
• NSC Number: 631363
• DSSTox Substance ID: DTXSID701034889
• Nikkaji Number: J456.338G,J464.988E
• Wikidata: Q76306144
• Pharos Ligand ID: QXQAGLBWW9PD
• Metabolomics Workbench ID: 130077
• ChEMBL ID: CHEMBL296411
• Mol file: 22255-22-7.mol

Synonyms:3,4',5-tri-O-methylresveratrol;3,4',5-trimethoxy-trans-stilbene;3,4',5-trimethoxystilbene;3,5,4'-tri-O-methyl-resveratrol;3,5,4'-tri-O-methylresveratrol;3,5,4'-trimethoxystilbene;BTM 0512;BTM-0512;BTM0512

Chemical Property of (E)-3,5,4'-Trimethoxystilbene

Chemical Property:

• Appearance/Colour: Pale yellow oil
• Vapor Pressure: 5.37E-07mmHg at 25°C
• Melting Point: 57 °C
• Refractive Index: 1.599
• Boiling Point: 423.8 °C at 760 mmHg
• Flash Point: 144.4 °C
• PSA: 27.69000
• Density: 1.105 g/cm³
• LogP: 3.88280
• Storage Temp.: ?20°C
• Solubility.: DMSO: ≥34mg/mL
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 270.125594432
• Heavy Atom Count: 20
• Complexity: 283

Purity/Quality:

99% ^*data from raw suppliers

ResveratrolTrimethylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53-41-37/38
• Safety Statements: 26-36/37/39-61-60-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=CC2=CC(=CC(=C2)OC)OC
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=C2)OC)OC
• 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.
• 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 A resveratrol analog with a variety of pharmacology action, including inst microtubule-destabilization 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.

Technology Process of (E)-3,5,4'-Trimethoxystilbene

There total 172 articles about (E)-3,5,4'-Trimethoxystilbene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) + methyl iodide (74-88-4) → 3,5,4'-trimethoxy-trans-stilbene (22255-22-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(00)00215-7

Reference yield: 100.0%

3,5,4'-trimethoxystilbene (22255-22-7,94608-23-8,63844-75-7) → 3,5,4'-trimethoxy-trans-stilbene (22255-22-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; for 8h; Reflux;

DOI:10.1016/j.tetlet.2009.04.023

Reference yield: 94.0%

4-methoxy-benzaldehyde (123-11-5) + diethyl 3,5-dimethoxybenzylphosphonate (108957-75-1) → 3,5,4'-trimethoxy-trans-stilbene (22255-22-7)

Guidance literature:

diethyl 3,5-dimethoxybenzylphosphonate; With sodium hydride; In tetrahydrofuran-d8; at 0 - 20 ℃; for 0.166667h; Inert atmosphere;

4-methoxy-benzaldehyde; In tetrahydrofuran; at 28 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.joc.6b03037

upstream raw materials:

diazomethane

3,4'-dimethoxy-5-hydroxystilbene

3,5-dimethoxy-4'-hydroxy-trans-stilbene

dimethyl sulfate

Downstream raw materials:

3,5-dimethoxybenzaldehdye

resveratrol

4-methoxybenzoic acid

3,5-dimethoxybenzoic acid

Refernces

• 1、 Polunin, Konstantin E.,Polunina, Irina A.,Schmalz, Hans-Guenther. "η6-arene-tricarbonylchromium complexes in the syntheses of trans-resveratrol and pinostilbene". . p. 178 - 179. Retrieved 2002.
• 2、 Cheong, Ho,Ryu, Shi-Yong,Kim, Kyeong-Man. "Anti-allergic action of resveratrol and related hydroxystilbenes". . p. 266 - 268. Retrieved 1999.
• 3、 Lara-Ochoa, Francisco,Sandoval-Minero, Leticia C.,Espinosa-Pérez, Georgina. "A new synthesis of resveratrol". . p. 5977 - 5979. Retrieved 2015.
• 4、 Rivera, Horacio,Shibayama, Mineko,Tsutsumi, Victor,Perez-Alvarez, Victor,Muriel, Pablo. "Resveratrol and trimethylated resveratrol protect from acute liver damage induced by CCI4 in the rat". . p. 147 - 155. Retrieved 2008.
• 5、 Polunin,Schmalz. "Application of chromium-arene complexes in the organic synthesis. Efficient synthesis of stilbene phytoalexins". . p. 252 - 261. Retrieved 2004.
• 6、 Anjaneyulu, A. S. R.,Raghava Reddy, A. V.,Reddy, D. S. K.,Ward, R. S.,Adhikesavalu, D.,Cameron, T. Stanley. "PACHARIN: A NEW DIBENZO(2,3-6,7)OXEPIN DERIVATIVE FROM BAUHINIA RACEMOSA LAMK". . p. 4245 - 4252. Retrieved 1984.
• 7、 -. "METHODS OF ARENE ALKENYLATION". Page/Page column 18; 66-68. . Retrieved 2021/11/26.
• 8、 Zhang, Zhao,Zhang, Dejiang,Zhu, Longzhi,Zeng, Dishu,Kambe, Nobuaki,Qiu, Renhua. "Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products". supporting information. p. 5317 - 5322. Retrieved 2021/06/28.