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[ CAS No. 529-40-8 ] {[proInfo.proName]}

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Chemical Structure| 529-40-8
Chemical Structure| 529-40-8
Structure of 529-40-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 529-40-8 ]

CAS No. :529-40-8 MDL No. :MFCD00017424
Formula : C17H14O7 Boiling Point : -
Linear Structure Formula :- InChI Key :BWORNNDZQGOKBY-UHFFFAOYSA-N
M.W : 330.29 Pubchem ID :5320287
Synonyms :

Calculated chemistry of [ 529-40-8 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 7.0
Num. H-bond donors : 3.0
Molar Refractivity : 86.97
TPSA : 109.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.83
Log Po/w (XLOGP3) : 3.28
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : -0.07
Log Po/w (SILICOS-IT) : 2.59
Consensus Log Po/w : 2.25

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.25
Solubility : 0.0186 mg/ml ; 0.0000563 mol/l
Class : Moderately soluble
Log S (Ali) : -5.25
Solubility : 0.00185 mg/ml ; 0.00000561 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.63
Solubility : 0.00771 mg/ml ; 0.0000233 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.41

Safety of [ 529-40-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P264-P270-P301+P310-P321-P330-P405-P501-P302+P352-P333+P313-P321-P261-P272-P280-P363-P501 UN#:2811
Hazard Statements:H301-H315-H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 529-40-8 ]

* 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.

  • Downstream synthetic route of [ 529-40-8 ]

[ 529-40-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 20188-85-6 ]
  • [ 492-61-5 ]
  • [ 6014-42-2 ]
  • [ 529-40-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In water at 100℃; for 1h;
  • 2
  • [ 908094-01-9 ]
  • [ 117-39-5 ]
  • [ 529-40-8 ]
  • [ 2068-02-2 ]
  • [ 1245-15-4 ]
  • [ 90-19-7 ]
YieldReaction ConditionsOperation in experiment
1: 16% 2: 14% 3: 22% 4: 13% In methanol; diethyl ether at 20℃; for 1h; Further byproducts given;
  • 3
  • [ 117-39-5 ]
  • [ 74-88-4 ]
  • [ 529-40-8 ]
  • [ 572-32-7 ]
YieldReaction ConditionsOperation in experiment
1: 28% 2: 60% With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere; regioselective reaction; 3.1.29. Synthesis of dimethylether 25 and trimethylether 31 To a solution of 1 (151 mg, 0.5 mmol) in dry DMF (20 ml) was added K2CO3 (276 mg, 2.0 mmol, 4.0 equiv.) and iodomethane (0.11 ml, 1.75 mmol, 3.5 equiv.) at room temperature. After 12 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 MgSO4, filtered and concentrated. The crude material was purified by column chromatography (25% ethyl acetate in petroleum ether) to yield 25 (46 mg, 28% yield) and 31 (103 mg, 60% yield) as yellow solids.3.1.30. 3,5-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-4H-chromen-4-one (25)Mp 185-186 °C. 1H NMR (CDCl3, 300 MHz) δ 3.86 (s, 3H, -OCH3), 3.98 (s, 3H, -OCH3), 5.70 (s, 1H, 3'-OH), 6.28 (d, J = 2.0 Hz, 1H, 6-H), 6.41 (d, J = 2.0 Hz, 1H, 8-H), 6.98 (d, J = 8.6 Hz, 1H, 5'-H), 7.68 (d, J = 2.0 Hz, 1H, 2'-H), 7.78 (dd, J = 2.0, 8.6 Hz, 1H, 6'-H), 12.68 (s, 1H, 5-OH). ESI-MS m/z: 331 [M + H]+, 353 [M + Na]+.3.1.31. 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one (31)Mp 148-149 °C. 1H NMR (CDCl3, 300 MHz) δ 3.87 (s, 6H, -OCH3), 3.99 (s, 3H, -OCH3), 5.70 (s, 1H, -OH), 6.35 (d, J = 2.2 Hz, 1H, 6-H), 6.44 (d, J = 2.2 Hz, 1H, 8-H), 6.96 (d, J = 8.6 Hz, 1H, 5'-H), 7.69 (d, J = 2.0 Hz, 1H, 2'-H), 7.78 (dd, J = 2.0, 8.6 Hz, 1H, 6'-H), 12.63 (s, 1H, 5-OH). ESI-MS m/z: 345 [M + H]+, 367 [M + Na]+.
With potassium carbonate In N,N-dimethyl-formamide at 25℃;
  • 4
  • [ 77-78-1 ]
  • [ 153-18-4 ]
  • [ 603-61-2 ]
  • [ 529-40-8 ]
  • [ 90-19-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: dimethyl sulfate; rutin With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 6h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 80℃; for 2h; 2.2.4 Synthesis of 4′-O-methylquercetin (15), 7-O-methylquercetin (16) and 4′, 7-O-dimethylquercetin (17) Rutin (200 mg, 0.328 mmol), K2CO3 (90.6 mg, 0.656 mmol), and dimethylsulfate (62.2 μL, 0.656 mmol) were added to 10 mL of DMF, and the mixture was stirred for 6 h at 65°C. The resulting mixture was added to 50 mL of 2.5 N HCl and refluxed at 80°C for 2 h. The reaction mixture was diluted with 150 mL of EtOAc and washed with water (2×150 mL). The reaction mixture was obtained by drying the EtOAc phase using Na2SO4. After evaporating the solvent, compounds 15, 16, and 17 were obtained by preparative HPLC with an ODS-3 column (20 mm φ×250 mm). Compounds were eluted with the linear gradient MeOH/0.05% aqueous solution of TFA (0 min, 60/40; 50 min, 100/0; 6 0min, 100/0) to obtain 15, 16 and 17 as yellowish powders with yields of 4.1%, 10.0%, and 7.7%, respectively. The structures of the synthesized compounds 15, 16, and 17 were confirmed using NMR, MALDI-TOFMS, UV and IR spectra, and by the measurements of specific optical rotation. Compound 15: UV λmax 207, 254, 368nm; [α]25D -26.9° (c 0.20, MeOH); IR (KBr) νmax 3430, 1655, 1617, 1499, 1456cm-1; 1H NMR (dimethylsulfoxide-d6, 600MHz) δH 3.81 (3H, s, 4′-OCH3), 6.15 (1H, d, J=2.04Hz, H-6), 6.39 (1H, d, J=2.04Hz, H-8), 7.05 (1H, d, J=8.22Hz, H-5′), 7.62 (1H, dd, J=8.22, 2.76Hz, H-6′), 7.63 (1H, d, J=2.10Hz, H-2′); 13C NMR (dimethylsulfoxide-d6,150MHz) δC 56.1 (4′-OCH3), 93.9 (C-8), 98.7 (C-6), 103.6 (C-4a), 112.4 (C-5′), 115.1 (C-2′), 120.3 (C-6′), 123.9 (C-1′), 136.7 (C-3), 146.7 (C-3′), 146.8 (C-2), 149.9 (C-4′), 156.7 (C-8a), 161.3 (C-5), 164.5 (C-7), 176.5 (C-4); MALDI-TOFMS m/z 317.0494 [M+H]+. (0015) Compound 16: UV λmax 206, 255, 371nm; [α]25D -17.3° (c 0.20, THF); IR (KBr) νmax 3402, 1656, 1593, 1502, 1442, 1324cm-1; 1H NMR (dimethylsulfoxide-d6, 600MHz) δH 3.82 (3H, s, 7-OCH3), 6.31 (1H, d, J=2.04Hz, H-6), 6.60 (1H, d, J=1.38Hz, H-8), 6.86 (1H, d, J=8.22Hz, H-5′), 7.56 (1H, dd, J=8.22, 2.04Hz, H-6′), 7.69 (1H, d, J=2.04Hz, H-2′); 13C NMR (dimethylsulfoxide-d6,150MHz) δC 56.5 (7-OCH3), 92.4 (C-8), 98.0 (C-6), 104.5 (C-4a), 115.6 (C-2′), 116.1 (C-5′), 120.5 (C-6′), 122.4 (C-1′), 136.6 (C-3), 145.6 (C-3′), 147.8 (C-2), 148.4 (C-4′), 156.6 (C-8a), 160.9 (C-5), 165.4 (C-7), 176.5 (C-4); MALDI-TOFMS m/z 317.0274 [M+H]+. (0016) Compound 17: UV λmax 206, 254, 368nm; [α]25D -3.72° (c 0.23, THF); IR (KBr) νmax 3420, 1656, 1594, 1501, 1441, 1332cm-1; 1H NMR (dimethylsulfoxide-d6, 600MHz) δH 3.82 (3H, s, 7-OCH3), 3.83 (3H, s, 4′-OCH3), 6.32 (1H, d, J=2.10Hz, H-6), 6.68 (1H, d, J=2.04Hz, H-8), 7.05 (1H, d, J=8.94Hz, H-5′), 7.65 (1H, dd, J=8.94, 2.04Hz, H-6′), 7.69 (1H, d, J=2.04Hz, H-2′); 13C NMR (dimethylsulfoxide-d6,150MHz) δC 56.2 (4′-OCH3), 56.6 (7-OCH3), 92.5 (C-8), 98.0 (C-6), 104.6 (C-4a), 115.3 (C-2′), 112.3 (C-5′), 120.3 (C-6′), 123.8 (C-1′), 137.0 (C-3), 146.7 (C-3′), 147.3 (C-2), 150.0 (C-4′), 156.7 (C-8a), 160.9 (C-5), 165.5 (C-7), 176.6 (C-4); MALDI-TOFMS m/z 331.0608 [M+H]+.
  • 5
  • [ 117-39-5 ]
  • [ 74-88-4 ]
  • [ 1486-70-0 ]
  • [ 529-40-8 ]
  • [ 2068-02-2 ]
  • [ 90-19-7 ]
YieldReaction ConditionsOperation in experiment
1: 30% 2: 25% 3: 19% 4: 19% With potassium carbonate In acetone at 20℃; for 3h; Preparation of mono- and di-O-methylated analogs ofquercetin (1) To a mixture of quercetin (1) (200 mg, 0.66 mmol) andanhydrous K2CO3 (114 mg, 0.82 mmol) in acetone (20 mL)was added CH3I (40 μL, d = 2.28 g/mL, 0.66 mmol) dropwise.The mixture was kept stirring at room temperature for2 h, and the progress of the reaction was monitored by TLC.A second lot (20 μL, 0.33 mmol) of CH3I was added andstirring was continued for another 1 h. Water (50 mL) wasadded and the mixture was extracted with EtOAc. Thecombined organic layer was washed with water, dried overanhydrous Na2SO4, and the solvent was evaporated invacuo. The crude products were chromatographed onSephadex LH-20 column eluting with MeOH to give threefractions (A1-A3). Fraction A1 was subjected to columnchromatography over silica gel eluted under isocratic conditionof 100% CH2Cl2 to yield the di-O-methyl ethers 4(34 mg, 25%) and 5 (26 mg, 19%). Fraction A3 wasrepeatedly chromatographed over silica gel eluted underisocratic condition of CH2Cl2-MeOH (10:0.05) to furnishthe mono-O-methyl ethers 2 (39 mg, 30%) and 3 (25 mg,19%), based on the unrecovered starting material, and thestarting material 1 (80 mg).
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