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CAS No. : | 58436-28-5 | MDL No. : | MFCD25973128 |
Formula : | C14H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HITJFUSPLYBJPE-UHFFFAOYSA-N |
M.W : | 230.26 | Pubchem ID : | 185914 |
Synonyms : |
3,4',5-Trihydroxybibenzyl;α,β-Dihydro-3,4',5-trihydroxystilbene;DHRSV
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 66.77 |
TPSA : | 60.69 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.52 cm/s |
Log Po/w (iLOGP) : | 1.71 |
Log Po/w (XLOGP3) : | 3.07 |
Log Po/w (WLOGP) : | 2.59 |
Log Po/w (MLOGP) : | 2.34 |
Log Po/w (SILICOS-IT) : | 2.75 |
Consensus Log Po/w : | 2.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.53 |
Solubility : | 0.0686 mg/ml ; 0.000298 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.01 |
Solubility : | 0.0224 mg/ml ; 0.0000974 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.01 |
Solubility : | 0.0227 mg/ml ; 0.0000986 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.59 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
97.82% | With 5%-palladium/activated carbon; hydrogen; In methanol; at 20℃; under 2250.23 Torr; for 3.0h; | In a 300 ml glass autoclave, 20 g of resveratrol, 130 g of methanol, and 0.2 g of 5% Pd / C were charged, nitrogen substitution was performed three times, and hydrogen substitution was performed three times. Under stirring, the reaction was carried out at room temperature under a hydrogen pressure of 3 kg / cm 2 for 3 hours. After the reaction, the reaction solution is filtered to remove Pd / C.Then, methanol was distilled off under reduced pressure to obtain 19.74 g (yield 97.82%) of hydrogenated resveratrol. |
95% | With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; under 3800.26 Torr; for 8.0h; | The molecular formula of dihydro-resveratrol was established as C,4H,403, which was obtained as white powders through hydrogenation of trans-resveratrol. A solution of trans-resveratrol (10 g, 43.8 mmol) in anhydrous EtOH (150 ml) was stirred at room temperature under 5 atm H2 pressure in the presence of 10% Pd/C (0.2 g). The reaction was quenched afier 8 hours (h), by filtering off the catalyst. The filtrate was evaporated in vacuum and the residue was subjected to silica gel chromatographic separation eluting with petroleum ether and ethyl acetate (1:1) to afford dihydro-resveratrol as white amorphous powder (9.6 g, 95% yield): HR-ESIMS ([M+1]+ mlz 231.1026, calcd 231.1016 for C,4H,503); ?H NMR (methanol-d4, 400 MHz) o 6.96 (2H,ABd, J=8.3 Hz), 6.67 (2H,ABd, J=8.4 Hz), 6.13 (2H, brd, J=2.2 Hz), 6.09 (1H, brt, J=2.2 Hz), 2.74 (2H, brdd, J=8.5, 5.6), 2.67 (2H, brdd, J=8.3, 5.2); ?3C NMR(methanol-d4, 100 MHz) 0 159.2 (2C, s), 156.3 (1C, s),145.6 (1C, s), 134.1 (1C, s), 130.3 (2C, d), 116.0 (2C, d),108.1 (2C, d), 101.1 (1C, d), 39.6 (2C, t), 38.0 (2C, t). |
92% | With 5%-palladium/activated carbon; hydrogen; In methanol; at 20℃; under 2250.23 Torr; for 3.0h;Autoclave; | In a 300 ml glass autoclave, 20 g resveratrol,130 g of methanol,5% Pd / C 0.2g is charged,Nitrogen replacement was performed 3 times and hydrogen replacement was performed 3 times.The mixture was reacted at room temperature with stirring under a hydrogen pressure of 3 kg / cm 2 for 3 hours.After the reaction, the reaction solution was filtered to remove Pd / C, and 100 g of methanol was distilled off under reduced pressure.This concentrated solution was added to 120 g of purified water to precipitate crystals and stirred at room temperature for 1 hour.The crystals were collected by filtration, washed with purified water, and dried under reduced pressure to obtain 18.56 g (yield 92.0%) of hydrogenated resveratrol. |
38% | With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 1.0h; | To a solution of the resveratrol (500 mg, 2.2 mmol) in methanol (1 mL) was added 10% palladium on carbon (200 mg). The mixture was stirred at ambient temperature under hydrogen atmosphere for 1 h. The reaction mixture was filtered with celite, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (40% ethylacetate in hexane) to give the desire compound 4f as a white solid (190 mg, 38%). 1H-NMR (400 MHz, CD3OD) delta 2.62-2.76 (4H, m), 6.08 (1H, t, J = 2.3 Hz), 6.12 (2H, d, J = 2.3 Hz), 6.66 (2H, d, J = 8.7), 6.96 (2H, d, J = 8.7 Hz) ; ESI-MS (negative ion): calcd for C14H13O3 ([M-H]-) 229.0870 ; found 229.0846 HPLC Purity >99% (R.T. = 3.0 min, under gradient conditions as below). |
With palladium 10% on activated carbon; hydrogen; In ethanol; for 3.0h; | General procedure: Dihydro derivatives of compounds 7, 9, 11, 13, 15, 17, 19, 21, and 23 were prepared by hydrogenation of corresponding stilbenes. A standard protocol was followed,32 with minor modifications. Solutions of each stilbene (10mg) in absolute EtOH (5ml) were stirred under H2 for 3h in the presence of 10% Pd/C. The reaction mixtures were filtered over Celite to remove the catalyst, and evaporated to dryness. The resulting residues were purified by flash column chromatography, using a hexane/EtOAc gradient, to afford target compounds 8, 10, 12, 14, 16, 18, 20, 22, and 24, respectively, in yields of 85-95%. The spectroscopic data of compounds were in agreement with the literature, except for compound 24, for which no report was found (1H NMR spectrum is provided as Supporting information).32-41 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; sodium chloride; In methanol; | Example 29 4-(3,5-Dihydroxyphenethyl)-phenol (29). A solution of potassium hydroxide in methanol was added to 4-(3,5-diacetoxyphenethyl)-acetoxybenzene in methanol then heated to 65 C. for 30 minutes under an argon atmosphere. The solution was then poured into water, acidified to pH 4 with 1 M HCl. NaCl was added and the solution extracted with EtOAc. The organic layer was separated and washed twice with saturated brine, then dried over anhydrous Na2SO4, filtered and rotary evaporated to give an orange solid. Purification by isocratic elution from column chromatography (0,040-0,063 mm SiO2) with 2:1 EtOAc/hexane gave 4-(3,5-diahydroxyphenethyl)-phenol as a white solid. Rf 0.44 (2:1 EtOAc/hexane); Mp: 160.5-161.0 C., 1H NMR (CD3OD): delta 2.61-2.75 (m, 4H, 2*CH2), 6.05 (pseudo t, 1H, J=2.2 Hz, 4'), 6.09-6.10 (m, 2H, 2',6'), 6.61-6.66 (m, 2H, Jortho=8.6 Hz, 3,5), 6.91-6.96 (m, 2H, 2,6); 13C JMOD NMR (CD3OD): delta 35.56, 37.08 (2*CH2), 98.81 (4'), 105.82 (2',6'), 113.66 (3,5), 128.01 (2, 6), 131.82 (1), 143.33 (1'), 153.85 (4), 156.80 (3', 5'); LRESI positive ion mass spectrum; m/z 231 (MH+, 100%), 232 (12%), 253 (MNa+, 11%); HRESI positive ion mass spectrum; MH+ calc. 231.1021, measured 231.1014. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium carbonate; In dimethyl sulfoxide; at 80℃;Inert atmosphere; | EXAMPLE 19 Synthesis of <strong>[58436-28-5]dihydroresveratrol</strong> phthalonitrile in one reaction pot-To a 1000 mL, three-necked flask fitted with a thermometer and a nitrogen inlet were added <strong>[58436-28-5]dihydroresveratrol</strong> (15.0 g, 65.1 mmol), 4-nitrophthalonitrile (35.0 g, 201 mmol), powdered anhydrous K2CO3 (27.9 g, 202 mmol), and DMSO (300 mL). The resulting mixture was degassed with nitrogen at ambient temperature and heated at 80 C. under a nitrogen atmosphere for 8-16 h. The mixture was allowed to cool to ambient temperature and poured into a 5% aqueous HCl solution resulting in the formation of a solid. The material was broken up and collected using a Buechner funnel. The white solid was washed with 200 mL of a 5% aqueous HCl solution, and finally with 200 mL portions of water until neutral. The isolated solid was vacuum dried to yield the amorphous <strong>[58436-28-5]dihydroresveratrol</strong> phthalonitrile (38.6 g, 97%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With decarboxylase specific for 2,6-dihydroxybenzoic acid isolated from Rhozobium sp.; In methanol; aq. phosphate buffer; water; at 30℃; for 24.0h;pH 5.5;Sealed tube; Enzymatic reaction; | The substrate (A-X), in solution in methanol (50 mg in 1 ml), is added to 19 mlof a phosphate buffer solution at pH 5.5 containing the whole cells (651 mg, producing thedecarboxylase specific for 2,6-dihydroxybenzoic acid isolated from Rhozobium sp.). This mixture is subsequently added to a 3M aqueous potassium hydrogencarbonate KHCO3 solution. The flask containing the reaction medium is sealed and stirred at 30C for 24 hours.The reaction is interrupted by addition of a 6M aqueous HC1 solution, until a pH of 2 is obtained. The aqueous phase thus obtained is extracted 4 times with ethyl acetate (10 ml). The organic phases are combined and dried over sodium sulfate. The solvent is evaporated under reduced pressure and the residue is purified by silica gel column chromatography (dichloromethane/methanol: 90/10), to result in the product (X) inthe form of an offwhite/yellow solid (yield: 45%).The 1H NMR spectrum and the mass spectrum are in accordance with the expected structure. |