Scutellarin synthesis
- Product Name:Scutellarin
- CAS Number:27740-01-8
- Molecular formula:C21H18O12
- Molecular Weight:462.36
119262-68-9
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27740-01-8
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Yield:27740-01-8 89%
Reaction Conditions:
Stage #1:scutellarein 7-O-β-D-glucuronopyranoside methyl ester with water;sodium hydroxide in acetone at 0; for 0.2 h;Inert atmosphere;
Stage #2: with hydrogenchloride in water;acetone; pH=2-3 for 1 h;Reagent/catalyst;Temperature;Time;Concentration;
Steps:
1.4 4. Preparation of 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid
A mixed solution of 300 mL water and 300 mL acetone was added to 20 g (42 mmol) of compound IV, and 70 mL of 10% aqueous sodium hydroxide was added dropwise under stirring at 0 °C. The reaction was stirred continuously under protection of nitrogen gas at 0 °C for about two hours, which was completed as detected by HPLC. 10% aqueous hydrochloric acid was added dropwise under stirring, to adjust pH to 2.0∼3.0, and stirred continuously for 1 hour followed by gradually raising to room temperature, with large amount of yellow solid 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid gradually separated out. The reaction mixture was left standing overnight at room temperature, filtered by suction, and the filter cake was washed with suitable amount of water and acetone, dried and then recrystallized with ethanol to obtain 17.3 g of pure 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid, with a yield of 89%. The purity was 98.74% detected by HPLC, the chromatogram detected by HPLC was shown in Figure 1, and the statistical result was shown in table 1. 1H-NMR (400MHz, DMSO), δ (ppm): 10.41 (1H, s), 8.63 (1H, s), 7.94 (2H, d, J= 8.8Hz), 6.99 (1H, s), 6.94 (2H, d, J= 8.8Hz), 6.86 (1H, s), 5.51-5.31 (3H, br), 5.28 (1H, d, J= 7.5 Hz), 4.11 (2H, d, J=9.6Hz), 3.43 (4H, m).
References:
Kunming Pharmaceutical Corp.;LI, Penghui;ZHANG, Wei;YANG, Zhaoxiang;ZHANG, Xiongbo;WANG, Jun;ZHU, Haibei;CHEN, Jinxin;BAI, Yiyang EP2840088, 2015, A1 Location in patent:Paragraph 0042
529-53-3
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27740-01-8
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$31.00/5mg
1180-46-7
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27740-01-8
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529-53-3
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2616-64-0
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27740-01-8
244 suppliers
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