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CAS No. : | 1447-88-7 | MDL No. : | MFCD00143504 |
Formula : | C16H12O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IHFBPDAQLQOCBX-UHFFFAOYSA-N |
M.W : | 300.26 | Pubchem ID : | 5281628 |
Synonyms : |
Dinatin;6-Methoxyapigenin;NSC 122415
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
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 |
---|---|---|
Multi-step reaction with 7 steps 1: 99 percent / K2CO3 / acetone / Heating 2: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 3: 59 percent / K2CO3 / acetone / Heating 4: pyridine / 3 h / 20 °C 5: KOH / pyridine / 4 h / 60 °C 6: sulfuric acid / acetic acid / 1.5 h / 60 °C 7: BCl3 / CH2Cl2 / 1.5 h / -65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38%; 49% | With potassium carbonate; In N,N-dimethyl-formamide; at 25.0℃; for 6.0h;Inert atmosphere; | To a stirring solution of 5 (200 mg, 0.67 mmol) in dry DMF (10 ml) was added K2CO3 (184 mg, 1.33 mmol, 2.0 equiv.) and iodomethane (0.07 ml, 1.00 mmol, 1.5 equiv.) at room temperature. After 6 h, the reaction mixture was then partitioned between 100 ml ethyl acetate and 100 ml water. The ethyl acetate layer was then washed with brine (100 ml), dried over Na2SO4, filtered and concentrated, the crude material was purified by column chromatography (25% ethyl acetate in petroleum ether) to afford 7 (80 mg, 38% yield) and 8 (103 mg, 49% yield) as yellow solids. 8 1H NMR (300 MHz, DMSO-d6) delta 3.40 (s, 3H, -CH3), 3.51 (s, 3H, -CH3), 6.63 (s, 1H, 3-H), 6.88 (s, 1H, 8-H), 7.19 (d, 2H, J = 8.7 Hz, 3',5'-H), 8.04 (d, 2H, J = 8.7 Hz, 2',6'-H), 10.91 (s, 1H, 7-OH), 13.07 (s, 1H, 5-OH); ESI-MS: m/z 313 [M - H]-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With DL-dithiothreitol; recombinant Plagiochasma appendiculatum flavone 6-O-methyltransferase; magnesium chloride; In aq. buffer; at 37℃; for 0.5h;pH 7.5;Enzymatic reaction;Kinetics; | General procedure: To demonstrate PaF6OMT activity and identify its preferredsubstrates, the enzyme was presented with variousflavonoids, phenylpropanoids, and coumarins. The 50-lLreactions used to test the activity of the purified enzymeeach comprised 200 mM Tris/HCl (pH 7.5), 4 mM DTT,2 mM MgCl2, 0.5 mM SAM, and 0.2 mM substrate and2 mug recombinant proteins. After incubating for 30 min at37 C, the reactions were stopped by the addition of anequal volume of acetonitrile. HPLC was performed using areverse phase 4.6 9 150 mm XDS-C18 column (Agilent,Palo Alto, CA, USA). The methanol (in water plus 0.1%(v/v) glacial acetic acid) gradient was 45-75% (v/v) for baicaleinand <strong>[529-53-3]scutellarein</strong>, 35-65% (v/v) for the other flavonoids,and 20-50% (v/v) for the phenylpropanoids andcoumarins. The flow rate was 1.0 mL*min-1. The reactionproducts from baicalein and <strong>[529-53-3]scutellarein</strong> were identified onthe basis of their NMR spectrum, as captured on anAV 600 spectrometer (Bruker, Karlsruhe, Germany) inDMSO-d6 with TMS as internal standard. |