Deoxyarbutin

Deoxyarbutin is a new effective lighten ingredient, can effectively inhibit tyrosinase activity and melanin synthesis to get significant and lasting lightening effect.

Under a nitrogen atmosphere, the compound (T-1) (19.1g, 227.0mmol) was dissolved in a p-toluenesulfonic acid pyridinium (PPTS) (5.7g, 22.7mmol) in dichloromethane (200ml) . After cooling to 10°C , the compound (T-7) (25.0g, 227.0mmol) was dropped slowly dichloromethane (100ml) solution. The reaction mixture is allowed to warm to 25°C. After stirring for 16 hours, poured into water (500ml). After the aqueous layer was extracted with dichloromethane, and the combined organic layer, water, saturated sodium hydrogen carbonate aqueous solution was washed successively with saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, the residue was purified by silica gel chromatography (volume ratio, toluene: ethyl acetate = 5: 1) to give the compound (T-8) (23.2g, 119.7mmol, 52.7 percent) was obtained.Example 17 Step 1; To a reaction flask containing a mixture of hydroquinone (110 g, 1.0 mol), pTSA (9.5 g, 0.05 mol), and 1 L of diethyl ether was added DHP (84 g, 1.0 mol) over a period of 30 min with stirring under a nitrogen atmosphere. After stirring overnight with nitrogen bubbling, the solution was extracted twice with nitrogen-purged solutions of 22.5 g of NaOH in 300 mL of water (total: 1.12 mol). The combined aqueous NaOH solutions were extracted with 300 mL of diethyl ether and cooled to 0° C. with an ice bath. Sodium bicarbonate (5.0 g) was added, and the stirred solution was slowly acidified with 64 mL of acetic acid (1.12 mol). The resulting mixture was stored at -18° C. overnight and then allowed to warm up to 0° C. The precipitated product was washed three times with 300 mL of water and dried under vacuum. The yield was 84 g (43percent). NMR showed that the product had a structure consistent with 4-(tetrahydro-2H-pyran-2-yloxy) phenol.To a 1-liter autoclave, 56.3 g (198 mmol) of the compound (9-2), 2.8 g of a catalyst (5percent Pd/C), and 250 ml of ethanol were added. The resulting mixture was reacted at room temperature for 3 hours while the hydrogen pressure was maintained to be 0.4 MPa. After the catalyst had been removed by filtration, vacuum concentration was performed. Hereby, 38.5 g of the compound (9-3) was prepared (quantitative)According to this procedure several other bases were tested (see table).Step 2; To a stirred solution of the product (30 g, 0.105 mol), calcium carbonate (2.79 g, 0.027 mol) and ethyl acetate (120 ml) was added palladium on carbon (3.6 g). The mixture was stirred at ambient temperature under hydrogen pressure until uptake of hydrogen ceased. The mixture was filtered and washed with ethyl acetate. The solvent was distilled off in vacuum. The evaporation residue was dissolved in alcohol (36 ml) and the product precipitated by the addition of water (144 ml). The slurry was cooled to 0According to this procedure several other bases were tested (see table).According to this procedure several other bases were tested (see table).According to this procedure several other bases were tested (see table).According to this procedure several other bases were tested (see table).In a pressure-resistant container, 6.7 g of the compound represented by the formula (I-1-4) 70 mL of tetrahydrofuran, 20 mL of ethanol, 10 mL of pyridine, 0.7 g of 5percent palladium carbon (containing 60percent of water) was added, 0.5 MPa, And the mixture was heated and stirred at 50 ° C. for 8 hours. The palladium was removed by filtration and the solvent was distilled off. Dissolve in ethyl acetate, add 1percent hydrochloric acid, Washed sequentially with water and brine. Purification was carried out by column chromatography (alumina, ethyl acetate) 4.1 g of a compound represented by the formula (I-1-5) was obtained.C3 (5.2 g, 11.5 mmol), 4-((tetrahydro-2H-piperan-2-yl) oxy) phenol (2.3 g, 12.08 mmol) and Cs2 CO3 (11.2 g, 34.5 mmol) Moore) was introduced into dimethyl sulfoxide (DMSO) (100 ml) and stirred at 120 C for 3 hours. After the reaction was completed, the reaction material was cooled to room temperature, diluted with water and extracted twice with EA. The organic layer was dried with MgSO4, and the mixture obtained by filtration was recrystallized with CHCl3 and EA to obtain C4 (5.3 g, yield 75%).

Molecular Weight:194.23
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:194.094294304
Monoisotopic Mass:194.094294304
Topological Polar Surface Area:38.7
Heavy Atom Count:14
Complexity:164
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes