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

Base Information

• Chemical Name: (Z)-3,5,4'-Trimethoxystilbene
• CAS No.: 94608-23-8
• Molecular Formula: C17H18O3
• Molecular Weight: 270.328
• DSSTox Substance ID: DTXSID501306933
• Nikkaji Number: J490.040E
• Pharos Ligand ID: QXQA6KRK612U
• ChEMBL ID: CHEMBL311636
• Mol file: 94608-23-8.mol

Synonyms:cis-trismethoxy Resveratrol;94608-23-8;(Z)-3,5,4'-TRIMETHOXYSTILBENE;CHEMBL311636;1,3-dimethoxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]benzene;(Z)-3,4',5-trimethoxystilbene;cis-Trismethoxyresveratrol;D03NTD;cis-Stilbene Derivative, 5a;SCHEMBL1006207;8Z-3,4',5-trimethoxystilbene;BDBM23940;(Z)-3,5,40-Trimethoxystilbene;GDHNBPHYVRHYCC-PLNGDYQASA-N;DTXSID501306933;HMS3648G16;3,4',5-trimethoxy-(Z)-stilbene;(Z)-3,5,4/'-Trimethoxystilbene;AKOS025401671;AC-24237;HY-121989;CS-0083811;A845021;SR-01000946368;SR-01000946368-1;,3-dimethoxy-5-[(1Z)-2-(4-methoxyphenyl)ethenyl]-benzene;1,3-dimethoxy-5-[(1Z)-2-(4-methoxyphenyl)ethenyl]benzene;1,3-dimethoxy-5-[(1z)-2-(4-methoxyphenyl)ethenyl]-benzene, AldrichCPR

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

Chemical Property:

• Melting Point: 55-57 °C
• Boiling Point: 423.774 °C at 760 mmHg
• Flash Point: 144.358 °C
• PSA: 27.69000
• Density: 1.105 g/cm³
• LogP: 3.88280
• Solubility.: ≤50mg/ml in DMSO;50mg/ml in dimethyl formamide
• 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:

98% ^*data from raw suppliers

cis-trismethoxyResveratrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

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: 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. cis-trismethoxy Resveratrol is a potent antioxidant found in grapes and red wine. Also, it is a resveratrol analog with increased antiproliferative activity towards a number of cancer cell lines.

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

There total 81 articles about (Z)-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: 92.0%

(Z)-4-hydroxy-3',5'-dimethoxystilbene (441351-32-2) + methyl iodide (74-88-4) → (Z)-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethene (94608-23-8)

Guidance literature:

With potassium carbonate; In acetone; for 5h; Heating;

DOI:10.1016/j.bmcl.2006.08.088

Reference yield: 90.0%

4-methoxy-benzaldehyde (123-11-5) + diethyl 3,5-dimethoxybenzylphosphonate (108957-75-1) → 3,5,4'-trimethoxystilbene (22255-22-7,94608-23-8,63844-75-7)

Guidance literature:

diethyl 3,5-dimethoxybenzylphosphonate; With sodium methylate; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h;

4-methoxy-benzaldehyde; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/acs.orglett.6b00010

Reference yield: 89.0%

1,3-dimethoxy-5-((4-methoxyphenyl)ethynyl)benzene (400608-31-3) → (Z)-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethene (94608-23-8)

Guidance literature:

With copper(I) thiophene-2-carboxylate; water; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium tert-butoxide; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane; In N,N-dimethyl-formamide; at 60 ℃; for 24h; Schlenk technique; Inert atmosphere; Glovebox;

DOI:10.1039/c9cc03213d

upstream raw materials:

(3,5-dimethoxybenzyl)triphenylphosphonium bromide

4-methoxy-benzaldehyde

3,5-dimethoxybenzyl 3,5-bis(trifluoromethyl)phenyl sulfone

(+/-)-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanol

Downstream raw materials:

resveratrol

3,5,4'-trimethoxy-trans-stilbene

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethane

Refernces

• 1、 Thiel, Niklas O.,Kaewmee, Benyapa,Tran Ngoc, Trung,Teichert, Johannes F.. "A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation". supporting information. p. 1597 - 1603. Retrieved 2020/02/05.
• 2、 Chen, Liu Zeng,Wu, Jing,Li, Kang,Wu, Qian Qian,Chen, Rui,Liu, Xin Hua,Ruan, Ban Feng. "Novel phthalide derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo". . . Retrieved 2020/08/21.