7508-05-6

Basic information

• Product Name: 2',3',4',6'-TETRAMETHOXYACETOPHENONE
• Synonyms: 2',3',4',6'-TETRAMETHOXYACETOPHENONE;2,4,5,6-TETRAMETHOXYACETOPHENONE;1-(2,3,4,6-tetramethoxyphenyl)ethanone
• CAS NO: 7508-05-6
• Molecular Formula: C₁₂H₁₆O₅
• Molecular Weight: 240.25
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 7508-05-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 55–56°C
• Boiling Point: 358.3 °C at 760 mmHg
• Flash Point: 158.1 °C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 2.58E-05mmHg at 25°C
• Refractive Index: 1.492
• CAS DataBase Reference: 2',3',4',6'-TETRAMETHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',4',6'-TETRAMETHOXYACETOPHENONE(7508-05-6)
• EPA Substance Registry System: 2',3',4',6'-TETRAMETHOXYACETOPHENONE(7508-05-6)

Safety Data

• Hazardous Substances Data: 7508-05-6(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of acetyl chloride with 1,2,3,5-tetramethoxybenzene (m.p. 47°), in the presence of aluminium chloride.

InChI:InChI=1/C12H16O5/c1-7(13)10-8(14-2)6-9(15-3)11(16-4)12(10)17-5/h6H,1-5H3

Upstream product

• 7446-70-0 aluminium trichloride 
• 5333-45-9 1,2,3,5-tetramethoxybenzene 
• 75-36-5 acetyl chloride 
• 7507-98-4 1-(2-hydroxy-3,4,6-trimethoxyphenyl)ethanone 
• 74-88-4 methyl iodide 
• 108-24-7 acetic anhydride 
• 530-55-2 2,6-dimethoxy-p-quinone 
• 15233-65-5 2,6-dimethoxy-1,4-hydroquinone 
• 2306-27-6 sinensetin 
• 77-78-1 dimethyl sulfate 
• 91291-60-0 (E)-1-(2,3,4,6-tetramethoxyphenyl)but-2-en-1-one 
• 64-19-7 acetic acid 

Downstream Products

• 112116-07-1 2',3',4',6'-tetramethoxy-2-methoxymethoxy-trans-chalcone 
• 859076-89-4 1-(4-methoxy-phenyl)-3-(2,3,4,6-tetramethoxy-phenyl)-propane-1,3-dione 
• 7507-87-1 2-Acetyl-3-hydroxy-5-methoxy-[1,4]benzochinon 
• 85563-78-6 3,4-methylenedioxy-2',4',5',6'-tetramethoxychalcone 
• 3162-28-5 2-hydroxy-3,4,5,6-tetramethoxyacetophenone 
• 53887-77-7 2-hydroxy-3,4,5,6-tetramethoxybenzene 
• 654083-34-8 1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(3,4-dimethoxyphenyl)-1,3-propanedione 
• 478-01-3 nobiletin 
• 2174-59-6 5-hydroxy-6,7,8,3',4'-pentamethoxyflavone 
• 21919-66-4 2,30dihydroxy-4,6-dimethoxyacetophenone 
• 23050-38-6 5,7,8-trimethoxy-2-phenyl-chromen-4-one 
• 4443-09-8 norwogonin 
• 116512-05-1 3,4-Bis-benzyloxy-benzoic acid 2-(3,4-bis-benzyloxy-phenyl)-5,7,8-trimethoxy-4-oxo-4H-chromen-3-yl ester 
• 116512-08-4 3',4'-bis(benzyloxy)-5,7,8-trimethoxy-3-tosyloxyflavone 

Relevant articles and documents

PET imaging of nobiletin based on a practical total synthesis

A practical synthesis of nobiletin, a polymethoxylated citrus flavone, was accomplished by utilizing our novel flavone synthesis. Synthetic nobiletin was labelled by selective demethylation and rapid incorporation of 11C atom. Positron emission tomography images successfully visualized the brain distribution, which may provide therapeutic benefits in the treatment of Alzheimer's disease. The Royal Society of Chemistry.

Improved, rapid and efficient synthesis of polymethoxyflavones under microwave irradiation and their inhibitory effects on melanogenesis

The microwave-assisted methylation of 2,5-dihydroxy-1,3-dimethoxybenzene with (CH3O)2SO2 for 5 min gave easily 1,2,3,5-tetramethoxybenzene, which was converted into pentamethoxybenzene. The microwave-assisted Friedel-Crafts acylation of pentamethoxybenzene in the presence of In(CF3SO3)3 gave pentamethoxyacetophenone for 15 min under solvent-free conditions in high yield. The microwave-assisted cyclization reaction of the diketones, which were synthesized from the acetophenone via three steps under microwave irradiation, gave the desired polymethoxyflavones for 1.5-3 min in high yields. The polymethoxyflavones showed inhibitory effects on melanogenesis in a human melanoma.

Chemical and Chemotaxonomical Studies of Filices. XLVII. Chemical Studies on the Constituents of Arachniodes nigrospinosa (CHING) CHING, A. festina (HANCE) CHING and A. mutica OHWI

Two new compounds, II and III, were isolated, together with 4-hydroxynicotinamide, from the fronds of both Arachniodes nigrospinosa and A. festina.The structures of II and III were elucidated as (E)-1-(2,3,4,6-tetramethoxyphenyl)but-2-en-1-one (E)-1-(2,3,4,6-tetramethoxyphenyl)pent-2-en-1-one, respectively.Ryomenin (I) was isolated from the fronds of A. mutica.Keywords - Arachniodes nigrospinosa; Arachniodes festina; Arachniodes mutica; Aspidiaceae; (E)-1-(2,3,4,6-tetramethoxyphenyl)but-2-en-1-one; (E)-1-(2,3,4,6-tetramethoxyphenyl)pent-2-en-1-one; ryomenin; 4-hydroxynicotinamide; phloroglucinol; chemotaxonomy.