84092-45-5

Usage

Preparation

Obtained by reaction of prenyl bromide with 2-hydroxy-4,6-di- (methoxymethoxy)aceto-phenone in methanolic potassium hydroxide solution, first at 0°, then at r.t. for 24 h (74%).

Upstream product

• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 870-63-3 prenyl bromide 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 13057-17-5 bromethyl methyl ether 
• 27364-71-2 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone 
• 115-18-4 2-methyl-3-buten-2-ol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 132246-42-5 5'-(3,3-dimethylallyl)-6'-hydroxy-3,4,2',4'-tetrakis(methoxymethoxy)chalcone 
• 118062-57-0 2-hydroxy-3-(3,3-dimethylallyl)-4,4',6-trimethoxymethoxy-3'-methoxy-chalcone 
• 199166-95-5 2-hydroxy-3-(3,3-dimethylallyl)-4,6-dimethoxymethoxychalcone 
• 1044743-43-2 1-[2-methoxy-4,6-bis(methoxymethoxy)-3-(3-methylbut-2-enyl)phenyl]ethanone 
• 1174035-58-5 (2Z)-4,6-bis(methoxymethoxy)-2-[4-(methoxymethoxy)benzylidene]-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3(2H)-one 
• 118525-40-9 icaritin 
• 27364-64-3 1-[4,6-dihydroxy-2-methoxy-3-(3-methylbut-2-enyl)-phenyl]ethanone 
• 1256842-55-3 C₂₇H₃₄O₉ 
• 650571-88-3 C₂₈H₃₆O₁₀ 
• 132246-43-6 8-(3,3-dimethylallyl)-5,7,3',4'-tetrakis(methoxymethoxy)flavanone 
• 132246-44-7 8-(3-methoxyisoamyl)-5,7,3',4'-tetrahydroxyflavanone 
• 132246-45-8 8-(3-hydroxyisoamyl)-5,7,3',4'-tetrahydroxyflavanone 
• 132339-92-5 6,6-dimethyl-4,5-dihydropyrano(2,3:7,6)-5,3',4'-trihydroxyflavanone 
• 13222-07-6 8-(3,3-dimethylallyl)-5,7,3',4'-tetrahydroxyflavanone 

Relevant academic research and scientific papers

Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin

The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug

Convenient and efficient total synthesis method for icaritin and derivatives of icaritin

The invention belongs to the field of natural medicine synthesis and particularly relates to a convenient and efficient total synthesis method for icaritin and derivatives of icaritin. The specific technical scheme is as follows: 2'-hydroxyacetophenone and benzaldehyde are used as raw materials, firstly, isopentene groups are introduced in aromatic rings of raw materials under the catalysis of anorganic polyacid metal ion complex, a flavonol framework is constructed under mild and green conditions, and an isopentenyl flavone compound comprising the icaritin and derivatives of icaritin is further synthesized. The method effectively overcomes the limitation of poor substrate solubility and poor regioselectivity when flavone is constructed firstly and then isopentene groups are introduced, the problems of frequent introduction and removal of protecting groups in a conventional isopentenylation method are solved, and the synthesis route is greatly simplified; and meanwhile, the problems of complex products and more byproducts in an isopentene group rearrangement method are solved. The total synthesis method provided by the invention is mild in condition, convenient to operate, high intotal yield and suitable for mass production of the isopentenyl flavone compound.

Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from Acronychia trifoliolata

Six acetophenone derivatives, acronyculatins I (1), J (2), K (3), L (4), N (5), and O (6), were recently isolated from Acronychia trifoliolata, and the structure of the known acronyculatin B (7) was revised. Because of the limited quantities of isolated p

A one-pot synthesis of aurones from substituted acetophenones and benzaldehydes: A concise synthesis of aureusidin

A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations. Georg Thieme Verlag Stuttgart New York.

Identification of SVM-based classification model, synthesis and evaluation of prenylated flavonoids as vasorelaxant agents

Support vector machine (SVM) was applied to predict vasorelaxation effect of different structural molecules. A good classification model had been established, and the accuracy in prediction for the training, test, and overall datasets was 93.0%, 82.6%, an

Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus

The minor hop (Humulus lupulus) chalcones 3′-geranylchalconaringenin (3), 5′-prenylxanthohuraol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1″,2″-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3′-geranyl-6′-O- methylchalconaringenin (2), 3′-methylflavokawin (6), and 2′-0-methyl-3′-prenylchalconaringenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC 50 values comparable to xanthohumol (8.2-19.2 μM). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.

Synthesis of four natural prenylflavonoids and their estrogen-like activities

Four prenylflavonoids, bavachin 1, isobavachin 2, 7,4′-dihydroxy-8- prenylflavone 3, and 8-prenylapigenin 4 were synthesized and recognized for possessing estrogen-like activity in MCF-7/BOS cells, as evaluated by an estrogen-screening assay. All compound

Synthesis of 5,7-dihydroxy-6,8-di-C-prenyl-4′-O-prenyl-flavanone

The prenylated flavanone (9) has been synthesized from phloroacetophenone (1). All the new products have been characterized by the spectral data and microanalysis.

Synthesis of 5,7,4'-trihydroxy-6-C-prenylflavone

5,7,4'-Trihydroxy-6-C-prenylflavone 6 isolated from the fruits of Maclura pomifera has been synthesized by the following route. Phloroacetophenone 1 on treatment with methoxymethyl chloride afford 2- hydroxy-4,6-di(methoxymethoxy) acetophenone 2 which on

Anti-ulcer agent comprising chalcone derivative as effective ingredient and novel chalcone derivative

The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: STR1 wherein X and Y independently stand for a hydrogen atom or together form a single bond, R1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R3 stands for hydroxyl group or a methoxy group, R4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R7 stands for a hydrogen atom or a methoxy group.