27364-71-2

Basic information

• Product Name: Ethanone, 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-
• Synonyms: dimethylallylphloracetophenone;1-[2,4,6-Trihydroxy-3-(3-methyl-but-2-enyl)-phenyl]-aethanon;Ethanone,1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl];1-[2,4,6-trihydroxy-3-(3-methyl-but-2-enyl)-phenyl]-ethanone;3'-prenyl-2',4',6'-trihydroxyacetophenone;6-O-demethylacronylin;2,4,6-trihydroxy-3-(3,3-dimethylallyl)acetophenone;1-acetyl-3-<3',3'-dimethylallyl-(1')>-phloroglucinol
• CAS NO: 27364-71-2
• Molecular Formula: C13H16O4
• Molecular Weight: 236.268
• Mol File: 27364-71-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 390.9±42.0 °C(Predicted)
• Density: 1.230±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Ethanone, 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-(27364-71-2)
• EPA Substance Registry System: Ethanone, 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-(27364-71-2)

Safety Data

• Hazardous Substances Data: 27364-71-2(Hazardous Substances Data)

Usage

Preparation

Preparation from 2,4-dihydroxy-6-methoxy-5- iso-pentenylacetophenone (Acronylin) by demethylation with aluminium chloride in refluxing benzene.

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 870-63-3 prenyl bromide 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 556-82-1 3-methyl-2-buten-1-ol 
• 108-73-6 3,5-dihydroxyphenol 
• 90632-20-5 1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl]ethanone 
• 358-72-5 dimethylallyl diphosphate 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 84092-45-5 2',4'-bis(methoxymethoxy)-5'-(3,3-dimethylallyl)-6'-hydroxyacetophenone 
• 1632152-52-3 (E)-5,7-dimethoxy-8-(3-methylbut-2-en-1-yl)-2-styryl-4H-chromen-4-one 
• 1632152-53-4 C₂₅H₂₆O₅ 
• 1632152-55-6 C₂₆H₂₈O₆ 
• 1632152-57-8 (E)-5-hydroxy-8,8-dimethyl-2-styryl-9,10-dihydropyrano[2,3-f]chromen-4(8H)-one 
• 1632152-58-9 (E)-5-hydroxy-2-(4-hydroxystyryl)-8,8-dimethyl-9,10-dihydropyrano[2,3-f]chromen-4(8H)-one 
• 1632152-59-0 C₂₂H₂₀O₆ 
• 1632152-46-5 C₂₄H₂₆O₅ 
• 1632152-47-6 C₂₅H₂₈O₆ 
• 1632152-48-7 C₂₆H₃₀O₇ 
• 33523-62-5 1-(2’-hydroxy-4’,6’-dimethoxy-3’-(3’’-methyl-2’’-buten-1’’-yl)phenyl)ethanone 
• 103629-80-7 cnidimol A 
• 118525-40-9 icaritin 
• 70872-24-1 (E)-1-(2-hydroxy-4,6-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: Application to 3′-prenylrubranine and petiolin D regioisomer

Efficient synthetic routes for biologically interesting polycycles with prenylated, geranylated, and farnesylated citrans were developed from several trihydroxybenzenes with prenyl, geranyl, and farnesyl groups on the benzene rings. Ethylenediamine diacet

Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones

American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.

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.