2,3',4,5'-Tetramethoxystilbene

Base Information

• Chemical Name: 2,3',4,5'-Tetramethoxystilbene
• CAS No.: 24144-92-1
• Molecular Formula: C₁₈H₂₀O₄
• Molecular Weight: 300.354
• DSSTox Substance ID: DTXSID101186212
• Nikkaji Number: J464.989C,J1.666.747A
• Wikidata: Q76304697
• Pharos Ligand ID: 3BDZ172L8QBX
• ChEMBL ID: CHEMBL46909
• Mol file: 24144-92-1.mol

Synonyms:2,3',4,5'-tetramethoxystilbene;2,4,3',5'-tetramethoxystilbene;3,5,2',4'-tetramethoxy-trans-stilbene;TMS cpd

Chemical Property of 2,3',4,5'-Tetramethoxystilbene

Chemical Property:

• Melting Point: 78-79 °C
• Boiling Point: 459.9 °C at 760 mmHg
• Flash Point: 152.3 °C
• PSA: 36.92000
• Density: 1.117g/cm³
• LogP: 3.89140
• Storage Temp.: Store at RT
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 300.13615911
• Heavy Atom Count: 22
• Complexity: 332

Purity/Quality:

99%, ^*data from raw suppliers

2,4,3'',5''-Tetramethoxystilbene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)C=CC2=CC(=CC(=C2)OC)OC)OC
• Isomeric SMILES: COC1=CC(=C(C=C1)/C=C/C2=CC(=CC(=C2)OC)OC)OC
• Recent ClinicalTrials: Study of Palifermin (Kepivance) in Persons Undergoing Unrelated Donor Allogeneic Hematopoietic Cell Transplantation
• General Description: TMS (2,3′,4,5′-tetramethoxystilbene) is a potent and selective inhibitor of human cytochrome P450 1B1 (CYP1B1), an enzyme involved in carcinogenesis and estrogen metabolism. It was identified as the most effective compound among a series of trans-stilbene derivatives, demonstrating high selectivity over other CYP isoforms (CYP1A1 and CYP1A2). Its inhibitory activity suggests potential applications in cancer chemoprevention by targeting CYP1B1-dependent estrogen activation pathways.

Technology Process of 2,3',4,5'-Tetramethoxystilbene

There total 35 articles about 2,3',4,5'-Tetramethoxystilbene 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: 95.0%

2,4-Dimethoxybenzaldehyde (613-45-6) + (3,5-dimethoxy-benzyl)phosphonic acid dimethyl ester (397333-50-5) → (E)-3,5,2',4'-tetramethoxystilbene (20578-92-1,24144-92-1,143207-87-8)

Guidance literature:

2,4-Dimethoxybenzaldehyde; (3,5-dimethoxy-benzyl)phosphonic acid dimethyl ester; With potassium hydroxide; 18-crown-6 ether; In dichloromethane; at 20 ℃;

With iodine; In n-heptane; for 12h; Further stages.; Heating;

DOI:10.1021/jm010298j

Reference yield: 78.0%

oxyresveratrol (4721-07-7,29700-22-9) + methyl iodide (74-88-4) → (E)-3,5,2',4'-tetramethoxystilbene (20578-92-1,24144-92-1,143207-87-8)

Guidance literature:

With potassium carbonate; In acetone; for 24h; Heating;

DOI:10.1016/j.bmcl.2006.08.018

Reference yield: 70.6%

E-2-(3,5-dimethoxyphenyl)-3-(2,4-dimethoxyphenyl)acrylic acid → (Z)-2,3',4,5'-tetramethoxystilbene (20578-92-1,24144-92-1,143207-87-8)

Guidance literature:

With quinoline; copper; at 220 ℃; for 3h; Inert atmosphere;

DOI:10.1248/cpb.58.1492

upstream raw materials:

3,5-dimethoxybenzaldehdye

(2,4-dimethoxybenzyl)triphenylphosphonium bromide

(E)-3-(2,4-Dimethoxy-phenyl)-acrylic acid 3,5-dimethoxy-phenyl ester

3,5-dimethoxybenzyltriphenylphosphonium chloride

Downstream raw materials:

oxyresveratrol

2,4,3',5'-tetramethoxy-bibenzyl

(Z)-2,3',4,5'-tetramethoxystilbene

Refernces

Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors

10.1021/jm010298j

The study focuses on the design, synthesis, and evaluation of trans-stilbene derivatives as potent and selective inhibitors of human cytochrome P450 1B1 (CYP1B1), an enzyme implicated in chemical carcinogenesis and estrogen metabolism. The researchers synthesized a series of trans-stilbene compounds containing a 3,5-dimethoxyphenyl moiety through an efficient solution phase synthetic pathway. These compounds were tested for their inhibitory activities on human cytochrome P450s, specifically CYP1A1, 1A2, and 1B1. The most selective and potent CYP1B1 inhibitor identified was 2,3′,4,5′-tetramethoxystilbene (7a). The study aimed to find compounds that could prevent mammary tumor formation by inhibiting CYP1B1-dependent estrogen metabolism, which may be valuable for the development of chemopreventive or therapeutic agents for cancer. The chemicals used in the study served as synthetic precursors for the stilbene derivatives and as tools to understand the structure-activity relationships of these compounds as CYP1B1 inhibitors.

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