39701-13-8

Upstream product

• 52200-61-0 2,4-dihydroxy-6-methoxy-5-methyl-acetophenone 
• 77-78-1 dimethyl sulfate 
• 23121-32-6 1-(2-hydroxy-4,6-dimethoxy-3-methyl-phenyl)-ethanone 
• 2657-28-5 2,4,6-trihydroxy-3-methyl-acetophenon 
• 74-88-4 methyl iodide 
• 14107-97-2 2,4,6-trimethoxytoluene 
• 75-36-5 acetyl chloride 
• 102749-22-4 1-(4,6-bis-benzyloxy-2-methoxy-3-methyl-phenyl)-ethanone 
• 830-79-5 2,4,6-trimethoxybenzaldehyde 
• 61040-78-6 2,4,6-trimethoxybenzyl alcohol 

Downstream Products

• 106929-57-1 3-methyl-2-hydroxy-4,6-bis(methoxymethoxy)acetophenone 
• 916917-16-3 8-methyl-5,7,4'-tris(methoxymethoxy)flavanone 
• 916917-28-7 (+/-)-8-Methylnaringenin 
• 2657-28-5 2,4,6-trihydroxy-3-methyl-acetophenon 

Relevant academic research and scientific papers

STRUCTURE DETERMINATION OF MELANERVIN, THE FIRST NATURALLY OCCURING FLAVONOID OF THE TRIPHENYLMETHANE FAMILY

From the flowers of Melaleuca quinquenervia (Myrtaceae) besides the flavonones strobopinin and kryptostrobin a new 8-aryl-flavonone has been isolated and shown to be (2,4-dihydroxy-6-methoxy)tolyl-3-(5,7-dihydroxy-6-methyl)flavanonyl-8-phenylmethane, mainly by degradation, MS, 1H- and 13C-NMR-spectroscopy.The new flavanone represents the first naturally occuring triphenylmethane compound.

Phloroglucinol derivatives as anti-tumor agents: synthesis, biological activity evaluation and molecular docking studies

Phloroglucinol compounds isolated from Dryopteris fragrans (L.) Schott showed a variety of biological activities, such as anticancer and anti-inflammatory. In this study, we have made a number of modifications around the scaffold of phloroglucinol and synthesized phloroglucinol derivatives A1–A9, B1–B9, and C1–C3. We synthesized these compounds and investigated their effect on four human cancer cell lines (A-549, MCF-7, Hela, HepG2 cell lines) via MTT assay in vitro. The results revealed that all compounds exhibited certain antiproliferative activities on cancer cell lines and excellent inhibitory effects on MCF-7, in which compound C2 was the best with the IC50 value of 18.49 μM, exceeding that of 5-fluorouracil. Moreover, the cell apoptosis test showed that compound C2 induced apoptosis in a concentration-dependent manner. Furthermore, the results of molecular docking analysis explained the probable interaction between the active compounds and active sites of target protein 4I22 and 1OG5. [Figure not available: see fulltext.]

Efficient synthesis of rottlerin and its two subunits

Rottlerin, a natural product isolated from Mallotus philippensis, is associated with a range of biological activities. Its chemical structure is featured by two different substituted phloroglucinol units linked by a methylene group. In this study, we accomplished a total synthesis of rottlerin using phenol-aldehyde condensation as the key reaction. By our method, gram-scale preparation of the two structural subunits was achieved, and rottlerin was obtained in a longest eight linear step with 20% overall yield. Our study provides a practical solution for obtaining the sample of rottlerin in an efficient way.

Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors α and β

In search of therapeutic agents for estrogen-related pathologies, phytoestrogens are being extensively explored. In contrast to naringenin, 8-prenylnaringenin is a potent hop-derived estrogenic compound, highlighting the importance of the prenyl group for hormonal activity. We investigated the effects of substituting the prenyl group at C(8) with alkyl chains of varying lengths and branching patterns on estrogen receptor (ER) subtype ERα- and ERβ-binding affinities and transcriptional activities. In addition, features of the ligand-induced receptor conformations were explored using a set of specific ER-binding peptides. The new 8-alkylnaringenins were found to span an activity spectrum ranging from full agonism to partial agonism to antagonism. Most strikingly, 8-(2,2-dimethylpropyl)naringenin exhibited full agonist character on ERα, but pronounced antagonist character on ERβ. Knowledge on how ER-subtype-selective activities can be designed provides valuable information for future drug or tool compound discovery.

Synthesis of aurentiacin

Aurentiacin 7 has been isolated from Pityrogramma triangularis var. pallida and synthesised from phloroacetophenone 1 in several steps. All the new products have been characterised on the basis of spectral data and micro analysis.

Studies of the selective O-alkylation and dealkylation of flavonoids. XVI. Demethylation of 2'-methoxyacetophenones with anhydrous aluminum chloride or bromide in acetonitrile

Demethylation of 2'-methoxyacetophenones with anhydrous aluminum chloride in acetonitrile was studied to survey its scope and limitations. The mechanism which the reaction proceeds via sterically constrained intermediates was proposed from the substituent effects. Additionally, dealkylation of 2'-benzyloxy-, 2'-ethoxy-, and 2'-isopropoxyacetophenones with two demethylating reagents, hydrochloric acid in acetic acid and anhydrous aluminum bromide in acetonitrile, was studied. It was found that the reactivity was greatly affected by the steric factor between the alkoxyl group and reagent. This behavior may have wide application in selection of protecting groups in organic synthesis.