20628-06-2

Basic information

• Product Name: 2'-HYDROXY-4',5'-DIMETHOXYACETOPHENONE
• Synonyms: AURORA KA-3659;4',5'-DIMETHOXY-2'-HYDROXYACETOPHENONE;4,5-DIMETHOXY-2-HYDROXYACETOPHENONE;1-(2-HYDROXY-4,5-DIMETHOXYPHENYL)ETHAN-1-ONE;2'-HYDROXY-4',5'-DIMETHOXYACETOPHENONE
• CAS NO: 20628-06-2
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 20628-06-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 113-114°C
• Boiling Point: 332.3 °C at 760 mmHg
• Flash Point: 130.6 °C
• Appearance: /
• Density: 1.172 g/cm³
• PKA: 10.29±0.23(Predicted)
• CAS DataBase Reference: 2'-HYDROXY-4',5'-DIMETHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-4',5'-DIMETHOXYACETOPHENONE(20628-06-2)
• EPA Substance Registry System: 2'-HYDROXY-4',5'-DIMETHOXYACETOPHENONE(20628-06-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 20628-06-2(Hazardous Substances Data)

Usage

Uses

1-(2-Hydroxy-4,5-dimethoxyphenyl)ethanone is a useful reagent in Vilsmeier-Haack reaction.

Preparation

Preparation by partial methylation of 2,5-dihydroxy-4-methoxyacetophenone, ? with methyl iodide in the presence of potassium carbonate in refluxing acetone (81%) ; ? with dimethyl sulfate in the presence of potassium carbonate in refluxing acetone (71%), in the presence of sodium methoxide in methanol (byproduct) or in the presence of sodium hydroxide in boiling aqueous ethanol (37%) ; ? with an excess of ethereal diazomethane in methanol (93%).

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 13252-95-4 8,9-dimethoxy-2-methyl-pyrano[3,2-c]chromene-4,5-dione 
• 64-19-7 acetic acid 
• 1818-27-5 1-(2,4,5-trihydroxyphenyl)ethanone 
• 77-78-1 dimethyl sulfate 
• 2033-89-8 3,4-dimethoxyphenol 
• 75-05-8 acetonitrile 
• 75-36-5 acetyl chloride 
• 1818-28-6 2',4',5'-trimethoxyacetophenone 
• 7732-18-5 water 
• 108-24-7 acetic anhydride 
• 7203-46-5 3,4-dimethoxyphenyl acetate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 22089-12-9 2,5-dihydroxy-4-methoxyacetophenone 
• 125130-61-2 (E)-3-(3,4-methylenedioxyphenyl)-1-(2'-hydroxy-4',5'-dimethoxyphenyl)-2-propen-1-one 
• 85288-45-5 2'-hydroxy-3,4,4',5'-tetramethoxy-trans-chalcone 
• 857554-36-0 (2-acetyl-4,5-dimethoxy-phenoxy)-acetic acid ethyl ester 
• 562836-43-5 4-(2-hydroxy-4,5-dimethoxy-phenyl)-2,4-dioxo-butyric acid ethyl ester 
• 1818-28-6 2',4',5'-trimethoxyacetophenone 
• 66003-52-9 3-(2-hydroxy-4,5-dimethoxy-phenyl)-3-oxo-propionaldehyde 
• 138008-71-6 2-acetyl-4,4,5-trimethoxy-2,5-cyclohexadienone 
• 138059-63-9 1-acetyl-2-hydroxy-4,5,5,6-tetramethoxy-1,3-cyclohexadiene 
• 118793-51-4 4-benzyloxy-2'-hydroxy-3,4',5'-trimethoxychalkone 
• 74375-76-1 2-(3',4'-methylenedioxybenzoyloxy)-4,5-dimethoxyacetophenone 
• 140447-86-5 4,2'-Dihydroxy-4',5'-dimethoxychalcone 
• 77607-80-8 1-(2'-hydroxy-4',5'-dimethoxyphenyl)-3-hydroxy-3-methyl-butan-1-one 

Relevant articles and documents

Synthesis, structure-activity relationship studies and evaluation of a TLR 3/8/9 agonist and its analogues

A comprehensive SAR study of a putative TLR 3/8/9 agonist was conducted. Despite the excitement surrounding the potential of the first small molecule TLR3 agonist with a compound that additionally displayed agonist activity for TLR8 and TLR9, compound 1 displayed disappointing activity in our hands, failing to match the potency (EC50) reported and displaying only a low efficacy for the extent of stimulated NF-κB activation and release. The evaluation of >75 analogs of 1, many of which constitute minor modifications in the structure, failed to identify any that displayed significant activity and none that exceeded the modest activity found for 1. [Figure not available: see fulltext.].

Synthesis and biological evaluation of novel chromonyl enaminones as α-glucosidase inhibitors

Series of novel chromonyl enaminones 1a–e and 2a–e and 3-alkylated chromones 3a–e were synthesized and evaluated in vitro as α-glucosidase inhibitors as well as antioxidant and antifungal agents. Antifungal activity was tested on strains of Candida albicans. Compounds 2a and 2d–e showed good inhibition of the α-glucosidase enzyme (IC50 = 5.5, 0.9, and 1.5 mM, respectively), their effect being better than that of 1a–e, 3a–e, and acarbose (the standard, IC50 = 7.73 ± 0.9 mM). The structure–activity relationship suggests that the phenyl group at the C-3 position of the chromone ring system and the 4-chlorophenyl group at the enaminone moiety (derivatives 2) increased the inhibition of α-glucosidase. Compounds 2a–e exhibited a slight antioxidant effect, and compounds 3a–e a moderate antifungal activity against C. albicans (IC50 70.5–83.1 μg/mL). Docking studies revealed that compounds 2 interact with the α-glucosidase residues of the binding pocket. Therefore, these chromone derivatives may be considered as potential α-glucosidase inhibitors, as well as antifungal agents against some Candida strains of yeast.

Divergent Total Syntheses of Flavonoid Natural Products Isolated from Rosa rugosa and Citrus unshiu

The concise and step-economical total syntheses of three hydroxyaurones and one polymethoxyflavone from readily available starting materials is described. A divergent synthetic strategy is employed, which centres on a common chalcone scaffold from which both the aurone and flavone frameworks can be accessed through the use of different oxidative cyclisation methods. These are the first reported total syntheses of these biologically interesting compounds.