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CAS No. : | 2092-49-1 | MDL No. : | MFCD00156888 |
Formula : | C16H14O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NSTQUZVZBUTVPY-UHFFFAOYSA-N |
M.W : | 302.28 | Pubchem ID : | 95086 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 79.68 |
TPSA : | 93.06 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.94 cm/s |
Log Po/w (iLOGP) : | 2.12 |
Log Po/w (XLOGP3) : | 1.7 |
Log Po/w (WLOGP) : | 2.41 |
Log Po/w (MLOGP) : | 0.46 |
Log Po/w (SILICOS-IT) : | 2.98 |
Consensus Log Po/w : | 1.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.86 |
Solubility : | 0.418 mg/ml ; 0.00138 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.27 |
Solubility : | 0.163 mg/ml ; 0.000538 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.91 |
Solubility : | 0.0375 mg/ml ; 0.000124 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
97% | With dipotassium peroxodisulfate; iron(II) sulfate In water at 80 - 120℃; for 1 h; | 5 g of vanillin, (33 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was dissolved in 200 ml of ion-exchanged water heated to 80 ° C. To this solution, 200 mg (0 72 mmol) of iron sulfate (manufactured by Wako Pure Chemical Industries, Ltd.) and 5 g (19 mmol, potassium peroxodisulfate manufactured by Wako Pure Chemical Industries, Ltd.) were added and heated at 120 ° C. for 1 hour And refluxed. After completion of the reaction, unreacted vanillin was removed by hot filtration to obtain an intermediate (a1) (yield 97percent). |
96% | With laccase from Trametes versicolor; oxygen In acetone at 20℃; for 24 h; Green chemistry; Enzymatic reaction | General procedure: A solution of phenol substrate (1–7) (1.5g) in acetone (20mL) was added to NaOAc buffer (180mL, 0.1M, pH 5.0). O2 was bubbled into the solution for 5 min. Laccase from Trametes versicolor (20U, 12.4mg) was added and the reaction was stirred at room temperature for 24 h. The precipitate was filtered off the solution and the product dried overnight at 80°C under vacuum. |
71% | With sodium persulfate; ferrous ammonium sulphate hexahydrate In water for 0.5 h; Heating | Divanillin was prepared as previously described for the preparation of diapocynin with modifications[30]. Vanillin (0.912 g, 6 mmol) was dissolved in 200 mL of hot water. Then, the heating wasturned off and ammonium iron(II) sulfate hexahydrate (118 mg, 0.3 mmol) and potassium persulfate(811 mg, 3.0 mmol) were added and stirred for 30 min. The precipitated product was filteredand washed with cold water. The product was re-dissolved by adding sodium hydroxide (50 mL,4 mol L-1) and filtered. The solution was acidified by adding hydrochloric acid (50 mL, 4 mol L-1).The precipitate was filtered and washed with cold water. The product was dried in vacuum overphosphorus pentoxide, yielding 0.64 g (71percent) of a yellow pale solid. The purity was confirmed byHPLC analysis in line with a diode array detector set at 254 nm (Jasco, Tokyo, Japan). The analyseswere carried on a Luna C18 reversed-phase column (250 x 4.6 mm, 5 m) using solvent A(aqueous formic acid 0.1percent) as a mobile phase and solvent B (formic acid 0.1percent in acetonitrile).The gradient was solvent A 90percent to 10percent in 22 min. The flow rate was 1 mL min-1. NMR spectrawere obtained using DMSO- D6 as solvent and internal reference for 1H and 13C (Bruker DRX400 spectrometer, MA, USA): 1H NMR (400 MHz) δ (ppm): 9.80±9.88 (m, 2OH), 9.82 (s,2CHO), 7.43±7.45 (m, 4 CH-Ar), 3.94 (s, 2 OCH3). 13C NMR (100 MHz) δ(ppm): 191.2(2CHO), 150.4 (2C), 148.1 (2C), 128.1 (2CH), 127.8 (2C), 124.6 (2C), 109.2 (2CH), 56.0(2OCH3) (S1 and S2 Figs). These results are consistent with those previously reported [31]. |
50% | With iron(III) chloride hexahydrate In water at 20 - 50℃; for 29 h; | To the mixture of 10 vanillin (32.9mmol) and 76 FeCl3.6H2O (36.2mmol) taken in a round bottom flask, 150mL of 12 water was added. The reaction mixture was shaken for few minutes and then heated at 50°C for 5h. Thereafter, the reaction mixture was kept on stirring for 24hat room temperature. The mixture was cooled on ice-bath for 30 min and vacuum filtered. The obtained precipitates were washed initially with water, then with methanol and finally dried in hot air oven to provide bisvanillin (9 1a) whose 77 structure was confirmed through NMR [44] and mass spectrometry. 5.2.1.1 77 Bisvanillin or 3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde (1a) (0019) Grey powder (Yield 50percent) m. p. 310–315°C, 1H NMR (DMSO‑d6, 300MHz): δ 9.85 (2H, s), 9.70 (2H, s), 7.36 (4H, s), 3.82 (6H, s); 13C NMR (DMSO‑d6, 75.4MHz): δ 191.5, 150.9, 148.6, 128.6, 128.1, 125.0, 109.8 and 56.8. HRMS-ESI: m/z [M+H]+ for C16H14O6, calculated 303.1073; observed 303.1068. |
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