18259-15-9

Basic information

• Product Name: PTEROSTILBENE
• Synonyms: TRANS-3,5-DIMETHOXY-4'-HYDROXYSTILBENE;3,5-DIMETHOXY-4'-HYDROXYSTILBENE;AKOS 236-80;(E)-4-(3,5-diMethoxystyryl)phenol;NSC 613735;PTEROCARPUS MARSUPIUM
• CAS NO: 18259-15-9
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.3
• Product Categories: Stilbenes (substituted)
• Mol File: 18259-15-9.mol
• Article Data: 57

Chemical Properties

• Melting Point: 89-92℃
• Boiling Point: 420.4°C at 760 mmHg
• Flash Point: 208.1°C
• Appearance: /
• Density: 1.169g/cm³
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Refractive Index: 1.639
• PKA: 9.47±0.15(Predicted)
• CAS DataBase Reference: PTEROSTILBENE(CAS DataBase Reference)
• NIST Chemistry Reference: PTEROSTILBENE(18259-15-9)
• EPA Substance Registry System: PTEROSTILBENE(18259-15-9)

Safety Data

• Hazard Codes: Xi:Irritant;; <
• Statements: R41:; R51/53:
• Safety Statements: S26:; S39:; S61:
• Hazardous Substances Data: 18259-15-9(Hazardous Substances Data)

Usage

General Description

Pterostilbene is a natural compound found in certain fruits, nuts, and plants, such as blueberries and grapes. It is a dimethylated derivative of resveratrol, another well-known antioxidant compound found in red wine. Pterostilbene has been studied for its potential health benefits, including anti-inflammatory, anti-cancer, and anti-aging properties. It has also shown promise in improving cognitive function, cardiovascular health, and diabetes management. Pterostilbene works as a powerful antioxidant, protecting cells from damage caused by free radicals and oxidative stress. Its ability to activate certain genes and signaling pathways also contributes to its overall health-promoting effects. Overall, pterostilbene holds promise as a natural compound with a wide range of potential health benefits.

InChI:InChI=1/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 1257314-98-9 (E)-2-(4-(3,5-dimethoxystyryl)phenoxy)tetrahydro-2H-pyran 
• 186581-53-3 diazomethane 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 848487-76-3 (E)-1-(4'-(methoxymethoxy)styryl)-3,5-dimethoxybenzene 
• 441351-31-1 trans-3,5-dimethoxy-4'-tert-butyldimethylsilyloxystilbene 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 637-69-4 4-Methoxystyrene 
• 25245-27-6 1-iodo-3,5-dimethoxybenzene 
• 74-88-4 methyl iodide 
• 878-00-2 4-formylphenyl acetate 
• 1532557-35-9 2-[(3,5-dimethoxybenzyl)sulfonyl]-1,3-benzothiazole 

Downstream Products

• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 952418-33-6 β-[4-[(1E)-2-(3,5-dimethoxyphenyl)-ethenyl]phenoxy]-α-(4-hydroxyphenyl)-3,5-dimethoxybenzeneethanol 
• 231300-43-9 C₃₂H₃₀O₆ 
• 60640-98-4 2,4-Dimethoxy-6-hydroxy-phenanthren 
• 441351-32-2 (Z)-4-hydroxy-3',5'-dimethoxystilbene 
• 1032508-02-3 (E)-S-4-(3,5-dimethoxystyryl)phenyl dimethylcarbamothioate 
• 1032508-00-1 trans-3',5'-dimethoxy-4-mercaptostilbene 

Relevant articles and documents

Antifungal activity of resveratrol derivatives against Candida Species

trans-Resveratrol (1a) is a phytoalexin produced by plants in response to infections by pathogens. Its potential activity against clinically relevant opportunistic fungal pathogens has previously been poorly investigated. Evaluated herein are the candidacidal activities of oligomers (2a, 3-5) of 1a purified from Vitis vinifera grape canes and several analogues (1b-1j) of 1a obtained through semisynthesis using methylation and acetylation. Moreover, trans-ε-viniferin (2a), a dimer of 1a, was also subjected to methylation (2b) and acetylation (2c) under nonselective conditions. Neither the natural oligomers of 1a (2a, 3-5) nor the derivatives of 2a were active against Candida albicans SC5314. However, the dimethoxy resveratrol derivatives 1d and 1e exhibited antifungal activity against C. albicans with minimum inhibitory concentration (MIC) values of 29-37 μg/mL and against 11 other Candida species. Compound 1e inhibited the yeast-to-hyphae morphogenetic transition of C. albicans at 14 μg/mL.

Determination and imaging of metabolites from Vitis vinifera leaves by laser desorption/ionisation time-of-flight mass spectrometry

Analysis of grapevine phytoalexins at the surface of Vitis vinifera leaves has been achieved by laser desorption/ionisation time-of-flight mass spectrometry (LDI-ToFMS) without matrix deposition. This simple and rapid sampling method was successfully applied to map small organic compounds at the surface of grapevine leaves. It was also demonstrated that the laser wavelength is a highly critical parameter. Both 266 and 337nm laser wavelengths were used but the 266nm wavelength gave increased spatial resolution and better sensitivity for the detection of the targeted metabolites (resveratrol and linked stilbene compounds). Mass spectrometry imaging of grapevine Cabernet Sauvignon leaves revealed specific locations with respect to Plasmopara viticola pathogen infection or light illumination.

Chalconoid and stilbenoid glycosides from Guibourtia tessmanii.

Phytochemical studies on the stem bark of Guibourtia tessmanii yielded a dihydrochalcone glucoside, 2',4-dihydroxy-4'-methoxy-6'-O-beta-glucopyranoside dihydrochalcone and a new stilbene glycoside, 3,5-dimethoxy-4'-O-(beta-rhamnopyranosyl-(1-->6)-beta- glucopyranoside) stilbene besides the known pterostilbene. Their structures were established on the basis of one and two dimensional NMR spectroscopic techniques, FABMS and chemical evidence.

Protective effect of piceatannol and bioactive stilbene derivatives against hypoxia-induced toxicity in H9c2 cardiomyocytes and structural elucidation as 5-LOX inhibitors

Stilbenes with well-known antioxidant and antiradical properties are beneficial in different pathologies including cardiovascular diseases. The present research was performed to investigate the potential protective effect of resveratrol (1) and piceatannol (2), against hypoxia-induced oxidative stress in the H9c2 cardiomyoblast cell line, and the underlying mechanisms. Compounds 1 and 2 significantly inhibited the release of peroxynitrite and thiobarbituric acid levels at na no- or submicromolar concentrations, and this effect was more evident in piceatannol-treated cells, that significantly increased MnSOD protein level in a concentration dependent manner. Furthermore, since piceatannol, which is far less abundant in natural sources, displayed a higher bioactivity than the parent compound, we hereby report on a very fast synthesis and detailed structure-based design of a focused stilbene library. Finally, taking into account that hypoxia-induced ROS accumulation also increases expression and activity of 5-lipoxygenase (5-LOX) with production of leukotrienes, we have disclosed structural key factors crucial for 5-LOX activity. Among the synthesized analogues (3–7), compound 7 was the most effective in improving cardiomyocytes viability and in 5-LOX inhibition. In conclusion, modeling and experimental studies provided the basis for further optimization of stilbene analogues as multi-target inhibitors of the inflammatory and oxidative pathway.

Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes

A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.