Acacetin synthesis
- Product Name:Acacetin
- CAS Number:480-44-4
- Molecular formula:C16H12O5
- Molecular Weight:284.26
Acacetin is an O-methylated flavone found in various plants. It is reported to demonstrate spasmolytic, antinociceptive, anti-inflammatory, and antioxidant activity in various research models. The solution of 2,4,6-trihydroxyacetophenone in acetone and K2CO3 was stirred at room temperature for 10 min and then 4-methoxybenzoyl chloride was added. The mixture was stirred under reflux for 24 h and purified to give Acacetin.
Yield:480-44-4 72%
Reaction Conditions:
with potassium carbonate in acetone at 65; for 24 h;Inert atmosphere;
Steps:
1.4. Synthesis of 2-p-methoxybenzyl-5,7-dihydroxychromone (2)
To a solution of 2,4,6-trihydroxyacetophenone (1.68 g, 10 mmol) in acetone under argon/open atmosphere, was added K2CO3 (13.82 g, 100 mmol, 10 equiv). The mixture was stirred at room temperature for 10 min and then 4-methoxybenzoyl chloride (2.56 g, 15 mmol, 1.5 equiv) was added. The mixture was stirred under reflux for 24 h. After cooling to room temperature the undissolved K2CO3 was filtered off, washed with acetone and evaporated under reduced pressure to a residue. The crude mixture was extracted with ethyl acetate (30 mL × 3), washed with water, brine, dried with anhydrous Na2SO4 and concentrated under reduced pressure to a residue. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (4:1) as eluent. Yield: 2.05 g (72%). Rf 0.17. Mp 138-142 °C. 1H NMR (400 MHz, DMSO) δ 2.07 (s, 1H), 2.63 (s, 1H), 3.56 (s, 3H), 6.29 (s, 1H), 6.96-7.11 (m, 2 H), 7.88-7.92 (m, 2H), 8.02-8.09 (m, 2H). 13C NMR (100.6 MHz, DMSO) δ 14.34, 30.79, 33.12, 40.13, 55.68, 60.51, 101.03, 108.68, 114.29, 130.25, 132.29, 156.56, 163.52, 204.59. MS (m/z): 285.27 (M + 1)+. Anal. Calcd for C16H12O5: C, 67.60; H, 4.25. Found: C, 67.49; H, 4.36.
References:
Zacharia, James T.;Hayashi, Masahiko [Carbohydrate Research,2012,vol. 348,p. 91 - 94] Location in patent:experimental part
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