Acacetin synthesis

8synthesis methods

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.

480-66-0 Synthesis

2',4',6'-Trihydroxyacetophenone monohydrate

480-66-0
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$10.00/1g

100-07-2 Synthesis

100-07-2
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$23.69/5g

480-44-4
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$27.00/5mg

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%). R_f 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.