Oroxylin A 7-O-beta-D-glucuronide methyl ester synthesis
- Product Name:Oroxylin A 7-O-beta-D-glucuronide methyl ester
- CAS Number:82475-02-3
- Molecular formula:C23H22O11
- Molecular Weight:474.4142
Yield:82475-02-3 91%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 20;
Steps:
3.3. Preparation of OAGME (2)
Baicalin methyl ester (7) (4.9 g, 10.65 mmol) was dissolved in 35 mL of DMF to whichK2CO3 (2.94 g, 2.0 eq) was added. It was cooled in an ice bath, dimethyl sulphate(1.5 mL, 1.5 eq) was added, and the reaction was allowed to stir over night at roomtemperature. After the completion of reaction (TLC), the mixture was poured, with stirring,into cold dilute HCl, and the precipitate was filtered, sucked dry to get OAGME(2) (4.6 g, 91%). NMR: 1H NMR (300 MHz, DMSO-d6) d ppm: 12.95 (1 H, s, 5-OH), 8.19(m, 2 H, Ar), 7.73 (m, 3 H, Ar), 7.15 (s, 1H, H-8), 7.07 (s, 1 H, H-3), 5.25 (d, 1 H, sugarH-1), 5.30-5.67 (m, 3 H, Sugar-OH protons), 4.27 (d, 1H, sugar H-5), 3.80 (s, 3 H,Ar-OMe), 3.70 (s, 3 H, OMe), 3.34-3.48 (m, 3 H, sugar H-2, H-3, H-4); 13C NMR (75 MHz,DMSO-d6) d ppm: 182.96, 169.63, 164.19, 156.62, 153.03, 152.74, 133.02, 132.65, 131.08, 129.62, 126.89, 106.60, 105.47, 99.74, 94.45, 76.09, 75.70, 73.21, 71.75, 60.77,52.45; mass: expected - 474.414 Da; observed - 475.123 (MH); m.p. 201-203 C(lit: 201 C).
References:
Hemantha, Hosahalli P.;Ramanujam, Rajendran;Majeed, Muhammed;Nagabhushanam, Kalyanam [Natural Product Research,2021,vol. 35,# 9,p. 1413 - 1420]
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