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CAS No. : | 578-74-5 | MDL No. : | MFCD00016787 |
Formula : | C21H20O10 | Boiling Point : | No data available |
Linear Structure Formula : | C15H9O5(C6H11O5) | InChI Key : | KMOUJOKENFFTPU-QNDFHXLGSA-N |
M.W : | 432.38 | Pubchem ID : | 5280704 |
Synonyms : |
|
Chemical Name : | 5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With water; ammonium hydroxide In methanol at 20℃; for 12 h; | Compound 1 (150 mg, 0.25 mmol) was added to a solution of 30percent 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: 72percent. 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium methylate In methanol; dichloromethane at 20℃; | Compound 9a (104 mg, 0.1 mmol) was dissolved in CH2Cl2 (2 mL) and anhydrous methanol (3 mL) was added. Sodium methoxide (100 mg, 1.85 mmol) was then added and the reaction was stirred at room temperature and monitored by TLC. Upon completion, the reaction was neutralized by adding freshly prepared 1 M HCl/MeOH solution to a pH value of 7.4. The solution was then concentrated under reduced pressure to give a yellow oil (crude product), which was further purified by preparative TLC plate to afford glycoside 9b as a white solid, 33 mg, 77percent. 1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, J = 8.8 Hz, 2H), 6.97 (d, J = 8.8 Hz, 2H), 6.86 (s, 1H), 6.84 (d, J = 1.4 Hz, 1H), 6.44 (d, J = 1.8 Hz, 1H), 5.07 (d, J = 7.5 Hz, 1H), 3.71 (d, J = 10.7 Hz, 1H), 3.47 – 3.21 (m, 5H); 13C NMR (100 MHz, DMSO-d6) δ 182.45 (C-4), 164.81 (C-7), 163.41 (C-2), 162.29 (C-5), 161.58 (C-9), 157.41 (C-4'), 129.05 (C-2',6'), 121.15 (C-1'), 116.58 (C-3',5'), 105.79 (C-10), 103.42 (C-3), 100.34 (Glc-C-1), 99.98 (C-6), 95.29 (C-8), 77.63 (Glc-C-3), 76.91 (Glc-C-5), 73.58 (Glc-C-2), 69.99 (Glc-C-4), 61.02 (Glc-C-6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.4 g | Stage #1: With aluminium(III) chloride hexahydrate In methanol at 70℃; for 15 h; Sealed tube Stage #2: With phosphoric acid In methanol for 0.5 h; Sonication |
5.0 g of 6H2O-aluminum trichloride, 100 ml of methanol,98percent wild luteolin 10g,70 sealed hydrolysis 15h, Adding phosphoric acid 6ml,Mixing,Ultrasound 30min,Adding 0.1percent phosphoric acid in 1000ml of the solution with stirring slowly, placing the mixture for 30 minutes, placing overnight, filtering and washing the filter cake to obtain a mixture of wild erosin, apigenin-7-O-glucoside and apigenin; The column was eluted with chloroform-methanol (12: 1), then apigenin was first eluted, and the ratio of chloroform to methanol was adjusted to (6: 1) to give apigenin-7-O- Glucoside 3.4g, determined by HPLC content of 98.3percent, and finally out of a small amount of wild lacquer glycosides |
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