Pterostilbene

Base Information

• Chemical Name: Pterostilbene
• CAS No.: 537-42-8
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.301
• Hs Code.: 29095000
• Mol file: 537-42-8.mol

Synonyms:4-Stilbenol,3',5'-dimethoxy-, (E)- (8CI);Phenol, 4-[2-(3,5-dimethoxyphenyl)ethenyl]-,(E)-;(E)-2-(3,5-Dimethoxyphenyl)-1-(4-hydroxyphenyl)ethene;(E)-4-Hydroxy-3',5'-dimethoxystilbene;3,5-Dimethoxy-4'-hydroxy-trans-stilbene;trans-3,5-Dimethoxy-4'-hydroxystilbene;

Chemical Property of Pterostilbene

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Melting Point: 89-92 °C
• Refractive Index: 1.639
• Boiling Point: 420.4 °C at 760 mmHg
• PKA: 9.96±0.26(Predicted)
• Flash Point: 208.1 °C
• PSA: 38.69000
• Density: 1.169 g/cm³
• LogP: 3.57980
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >20mg/mL

Purity/Quality:

99% ^*data from raw suppliers

Pterostilbene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, N
• Hazard Codes: Xi,N
• Statements: 41-51/53
• Safety Statements: 26-39-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Pterostilbene is a fragrant-smelling hydrocarbon called "styrene", which is a derivative of resveratrol. It is found in blueberries and Pterocarpus marsupium (PM) heartwood. It has anti-inflammatory, anti-thrombotic, anti-cancer, anti-cancer, anti-hyperlipidemia and antibacterial effects.
• Uses: Substantial studies demonstrate that pterostilbene has diverse pharmacological activities for the prevention and treatment of diseases including inflammation, cancer, diabetes, and dyslipidemia.Pterostilbene has been used:to investigate its anti-oxidative stress activities and the involvement of the nuclear factor (erythroid-derived 2)-like 2 (Nrf2)-antioxidant response element (ARE) signaling pathwayto determine its effects on transcriptional activation of estrogen receptor-α (ERα) in hormone resistant breast cancer cells)

Technology Process of Pterostilbene

There total 72 articles about Pterostilbene 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%

(E)-1-(4'-acetoxyphenyl)-2-(3,5-dimethoxyphenyl)ethene (18259-14-8,63366-83-6) → 3,5-dimethoxy-4'-hydroxy-trans-stilbene (537-42-8,18259-15-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 2h; Heating;

DOI:10.1016/j.tetlet.2008.07.087

Reference yield: 93.0%

(E)-1-(4'-(methoxymethoxy)styryl)-3,5-dimethoxybenzene (848487-76-3) → 3,5-dimethoxy-4'-hydroxy-trans-stilbene (537-42-8,18259-15-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; Heating;

DOI:10.1021/jm049238e

Reference yield: 90.0%

trans-3,5-dimethoxy-4'-tert-butyldimethylsilyloxystilbene (441351-31-1) → 3,5-dimethoxy-4'-hydroxy-trans-stilbene (537-42-8,18259-15-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2006.08.088

upstream raw materials:

trans-3,5-dimethoxy-4'-tert-butyldimethylsilyloxystilbene

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

dimethyl sulfate

(E)-1-(4'-(methoxymethoxy)styryl)-3,5-dimethoxybenzene

Downstream raw materials:

3,5-dimethoxybenzoic acid

(E)-O-4-(3,5-dimethoxystyryl)phenyl dimethylcarbamothioate

pinostilbene

(E)-dibenzyl 4-(3,5-dimethoxystyryl)phenyl phosphate

Refernces

• 1、 Peng, Yi,Fan, Yan-Hui,Li, Si-Yuan,Li, Bin,Xue, Jing,Deng, Qing-Hai. "Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage". supporting information. p. 8389 - 8394. Retrieved 2019/10/16.
• 2、 Boccellino, Mariarosaria,Donniacuo, Maria,Bruno, Ferdinando,Rinaldi, Barbara,Quagliuolo, Lucio,Ambruosi, Marika,Pace, Simona,De Rosa, Mario,Olga?, Abdurrahman,Banoglu, Erden,Alessio, Nicola,Massa, Antonio,Kahn, Haroon,Werz, Oliver,Fiorentino, Antonio,Filosa, Rosanna. "Protective effect of piceatannol and bioactive stilbene derivatives against hypoxia-induced toxicity in H9c2 cardiomyocytes and structural elucidation as 5-LOX inhibitors". . p. 637 - 647. Retrieved 2019/07/31.