ChemicalBook CAS DataBase List Apigenin 7-glucoside

Apigenin 7-glucoside synthesis

6synthesis methods

Product Name:Apigenin 7-glucoside
CAS Number:578-74-5
Molecular formula:C21H20O10
Molecular Weight:432.38

4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]-

119249-30-8
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578-74-5
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Yield:578-74-5 72%

Reaction Conditions:

with water;ammonium hydroxide in methanol at 20; for 12 h;

Steps:

3.17. Synthesis of apigenin-7-O-β-d-glucoside (5)

Compound 1 (150 mg, 0.25 mmol) was added to a solution of 30% aq NH₃·H₂O (5 mL) in CH₃OH (20 mL) with stirring. After stirring for 12 h at room temperature, the solvent was removed under reduced pressure. The residual was chromatographed on silica gel using ethyl acetate/MeOH (3:1) as eluent to afford the yellow solid 78 mg, yield: 72%. Mp 234-236 °C. (lit. 13, 238-239 °C); IR (KBr, cm^-1) 3440, 2918, 1615, 1563, 1452, 1346, 1273, 1245, 1146, 1103, 1072, 1024, 895; ¹H NMR (400 MHz, DMSO-d₆) δ 12.97 (s, 1H, OH-5), 10.48 (s, 1H, OH-4'), 7.96 (d, J = 8.8 Hz, 2H, H-2', H-6'), 6.94 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.87 (s, 1H, H-3), 6.83 (d, J = 1.6 Hz, 1H, H-8), 6.45 (d, J = 1.6 Hz, 1H, H-6), 5.42 (d, J = 8.0 Hz, 1H, H-1), 5.15 (s, 1H, OH-2), 5.08 (s, 1H, OH-3), 5.06 (s, 1H, OH-4), 4.63 (s, 1H, OH-6), 3.72-3.70 (m, 1H, H-2), 3.49-3.18 (m, 5H, H-3,4,5, 6); ¹³C NMR (100 MHz, DMSO-d₆) δ 60.6, 69.6, 73.1, 76.5, 77.2, 94.8, 99.6, 99.9, 103.1, 105.4, 116.0, 121.1, 128.6, 156.9, 161.1, 161.4, 163.0, 164.3, 180.1; HRMS [M+Na]⁺ calcd for C₂₁H₂₀O₁₀Na 455.3665, found 455.3649.