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

578-74-5

Compound 1 (CAS: 119249-30-8, 150 mg, 0.25 mmol) was dissolved in a mixture of methanol (20 mL) and 30% ammonia (5 mL) under stirring conditions. The reaction mixture was stirred continuously for 12 hours at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate/methanol (3:1, v/v) as eluent to afford the target product 5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-benzopyran-4-one , a yellow solid (78 mg, 72% yield). The melting point of the product was 234-236°C (literature value: 238-239°C). The infrared spectrum (KBr pressed sheet, cm^-1 ) showed characteristic absorption peaks: 3440, 2918, 1615, 1563, 1452, 1346, 1273, 1245, 1146, 1103, 1072, 1024, 895. the NMR hydrogen spectrum (400 MHz, DMSO-d6) δ: 12.97 (s, 1H, OH-5), 10.48 (s, 1H, OH-5), 10.47 (s, 1H). 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), 6.45 (d, J = 1.6 Hz, 1H, H-8), 6.45 (d, J = 1.6 Hz, 1.6 Hz, 1.6 Hz), 6.85 (d, J = 1.6 Hz, 1.6 Hz, 1.6 Hz, 1.6 Hz, 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). NMR carbon spectrum (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. The calculated value of [M + Na]+ C21H20O10Na by high resolution mass spectrometry (HRMS) was 455.3665 and the measured value was 455.3649.

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.