54900-97-9

Upstream product

• 6652-32-0 3,5-dimethoxybenzylchloride 
• 603-35-0 triphenylphosphine 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 705-76-0 3,5-dimethoxybenzyl alcohol 

Downstream Products

• 20578-92-1 (E)-3,5,2',4'-tetramethoxystilbene 
• 125910-10-3 1,2-bis(3,5-dimethoxyphenyl)ethylene 
• 80715-09-9 (E)-3,3',5,5'-tetramethoxystilbene 
• 537-42-8 3,5-dimethoxy-4'-hydroxy-trans-stilbene 
• 441351-32-2 (Z)-4-hydroxy-3',5'-dimethoxystilbene 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 94608-23-8 (Z)-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethene 
• 1310538-30-7 C₁₈H₂₀O₄ 
• 1310538-28-3 C₁₉H₂₂O₅ 
• 1310538-29-4 C₁₉H₂₂O₅ 
• 1387531-46-5 cis-3-(3,4-dimethoxyphenyl)-6-(3,5-dimethoxystyryl)coumarin 
• 1387531-47-6 trans-3-(3,4-dimethoxyphenyl)-6-(3,5-dimethoxystyryl)coumarin 
• 1387531-51-2 trans-7-(3,5-dimethoxystyryl)-3-phenylcoumarin 
• 1387531-56-7 trans-7-(3,5-dimethoxystyryl)-3-(4-methoxyphenyl)coumarin 

Relevant academic research and scientific papers

Preparation method of resveratrol

The invention discloses a preparation method of resveratrol. The preparation method comprises that (1), 3, 5-dimethoxybenzhydrol is chloroformed under the action of triphosgene to form 3, 5-dimethoxybenzyl chloride, (2), 3, 5-dimethoxybenzyl chloride reacts with triphenylphosphine to produce phosphorus ylide, (3), phosphorus ylide and p-methoxybenzaldehyde form a cis-trans-isomer mixture of 3, 4',5-trimethoxydistyrene under the action of lithium hydroxide, (4), 3, 4', 5-trimethoxystilbene, aluminum and iodine are added to acetonitrile, the mixture is cooled to the room temperature so that yellow solids are separated, the yellow solids are filtered, the filtrate acetonitrile is directly recovered and recycled, 6N hydrochloric acid and ethyl acetate are added into the filter cake, the mixture is stood for layering, wherein the water layer contains ethyl acetate extract, the organic phases are mixed, the organic phases are washed through a saturated salt solution, anhydrous sodium sulfate is dried and filtered, the solvent is removed in vacuum through a water pump, and the organic phase is recrystallized through ethanol and water so that resveratrol is obtained. The preparation method utilizes easily available raw materials, is easy to operate and control, is environmentally friendly, produces easily purified products, has a high yield and is suitable for industrial production.

Synthesis and biological evaluation of resveratrol-coumarin hybrid compounds as potential antitumor agents

Eighteen resveratrol-coumarin hybrid compounds (6 or 7-styryl-3- phenylcoumarin) were designed, synthesized and thirteen compounds were evaluated for their antitumor activities against MCF-7, HCT-28, and K562 tumor cell lines. Among them, compounds 2Z, 2E, 5E, and 7E showed varying degrees of growth inhibition of the above cell lines (IC50: 3.78-19.16 μmol/L). On the basis of the biological results, structure-activity relationships were obtained and discussed.

Complete NMR data of methoxylated cis- and trans-stilbenes as well as 1,2-diphenylethanes

Resveratrol is a polyphenol isolated from many natural sources including grapes, mulberries, eucalyptus, spruce, lilies, and peanuts. The hydroxyl groups in polyphenols can be substituted with various functional groups, allowing production of multiple derivatives. NMR spectroscopy is used to identify new derivatives. Since the complete NMR data of the known derivatives can be useful for identification of the newly isolated derivatives, here, we report the synthesis of 14 methoxylated stilbenes and four 1,2-diphenylethanes and their NMR data.

Pentiptycene-derived light-driven molecular brakes: Substituent effects of the brake component

Five pentiptycene-derived stilbene systems (1R; R = H, OM, NO, Pr, and Bu) have been prepared and investigated as light-driven molecular brakes that have different-sized brake components (1Hrot = 108-109 s-1) with little interaction with the brake component in the trans form ((E)-1R), which corresponds to the brake-off state. When the brake is turned on by photoisomerization to the cis form ((Z)-1R), the pentiptycene rotation can be arrested on the NMR spectroscopic timescale at temperatures that depend on the brake component. In the cases of (Z)-1NO, (Z)-1Pr, and (Z)-1Bu, the rotation is nearly blocked (krot = 2-6 s-1) at 298 K. It is also demonstrated that the rotation is slower in [D6]DMSO than in CD2Cl 2. A linear relationship between the free energies of the rotational barrier and the steric parameter A values is present only for (Z)-1H, (Z)-1OM, and (Z)-1NO, and it levels off on going from (Z)-1NO to (Z)-1Pr and (Z)-1Bu. DFT calculations provide insights into the substituent effects in the rotational ground and transition states. The molar reversibility of the E-Z photoswitching is up to 46%, and both the E and Z isomers are stable under the irradiation conditions.

Wittig-type olefination of alcohols promoted by nickel nanoparticles: Synthesis of polymethoxylated and polyhydroxylated stilbenes

Nickel nanoparticles were found to promote the Wittig-type olefination of primary alcohols with phosphorus ylides. The latter can be prepared from the corresponding phosphonium salts with TiBuLi or in situ generated with lithium metal. The methodology is especially efficient for the synthesis of stilbenes and is applied in the absence of any additive as a hydrogen acceptor. A new approach, to the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol, DMU-212 and analogues, is presented.

The design, synthesis, and anti-tumor mechanism study of N-phosphoryl amino acid modified resveratrol analogues

A novel series of trans-N-phosphoryl amino acid modified resveratrol analogues were synthesized and evaluated in vitro for their cytotoxic effects against CNE-1 and CNE-2 cell lines. These analogues showed good anti-proliferative activity, among which 8d, 8e, 8j, and 9d displayed much stronger inhibition effect than resveratrol and 8d showed the most potent activity with IC50 value at 3.45 ± 0.82 μM. The anti-tumor effects of 8d, 8e, 8j, and 9d were due to the induction of apoptosis, confirmed by the DNA fragmentation and flow cytometry analysis using PI (propidium iodide) staining and Annexin-V-FITC/PI staining assay. The PI staining assay also showed that 8d, 8e, 8j, and 9d caused cell cycles arrest at G0-G1 phase which finally led to cell apoptosis. Further mechanism study on compound 8d against CNE-2 cells has shown the PARP cleavage, which is a hallmark of caspase-3 activation, as well as the activation of caspase-9, and the intracellular ROS generation. These results all suggest that 8d induced a mitochondrial-dependent apoptosis pathway.

VO(acac)2-catalyzed oxidative coupling reactions of phosphonium salts

A novel eco-safer protocol for the preparation of symmetric or unsymmetric olefins directly from phosphonium salts under oxygen atmosphere in the presence of VO(acac)2 (1.0 mol%) was developed.