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

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 18259-14-8 (E)-1-(4'-acetoxyphenyl)-2-(3,5-dimethoxyphenyl)ethene 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 540-38-5 p-Iodophenol 
• 2628-16-2 p-acetoxystyrene 
• 25245-27-6 1-iodo-3,5-dimethoxybenzene 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 40243-87-6 3,5-dimethoxystyrene 
• 106-41-2 4-bromo-phenol 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 74-88-4 methyl iodide 

Downstream Products

• 1132-21-4 3,5-dimethoxybenzoic acid 
• 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.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Preparation method of resveratrol compound

The invention provides a preparation method of a resveratrol compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: firstly, carryingout oxidation addition and reduction elimination reaction on alkoxy-substituted benzyl halide, alkoxy-substituted benzaldehyde and a metal catalyst to obtain alkoxy-substituted diacetophenone; then carrying out reduction, reverse elimination and selective debenzylation reaction on the alkoxy-substituted diacetophenone and the metal catalyst in a hydrogen atmosphere to obtain the resveratrol compound. In the preparation method, hydrogenation reduction, reverse elimination and selective debenzylation reaction can be achieved through a one-pot method, trans-olefin is directly obtained through thereaction, and the generation of isomers is avoided; the Lewis acid is removed from the source through the selective catalytic debenzylation of the reaction, so that the method has the advantage of high yield, and is an environment-friendly process. Experimental results show that the products obtained by the preparation method are trans-olefins, the purity can reach more than 99.5%, and the yieldis more than 80%.