Cosmetic for skin whitening containing acyl substituted derivatives of glucose or sucrose
A technology for skin whitening and cosmetics, applied in the field of skin whitening cosmetics, can solve the problems of low synthesis rate, difficult synthesis, and inability to commercialize, and achieves the effects of efficiently inhibiting the formation of melanin, efficient skin whitening, and easy synthesis
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Embodiment 1
[0033] Synthesis Example 1 (Synthesis Example of Glucose Isovalerate Derivatives)
[0034] Put 5g (27.8mmol) of glucose in a double-neck round bottom flask, add 50ml of pyridine and dissolve it completely in a water bath. The solution was maintained at 0°C, and 5.5 equivalents of anhydrous isovaleric acid was slowly added dropwise, and after stirring for 3 hours, 5.5 equivalents of anhydrous isovaleric acid was added again. The temperature was raised to 25°C for 30 hours. 150 ml of methanol was added to stop the reaction, the solvent was completely removed under reduced pressure, and 300 ml of chloroform was added. The resulting product was washed twice with 250 ml of 1N hydrochloric acid and 250 ml of saturated aqueous sodium bicarbonate solution, respectively. The chloroform layer was sucked dry under reduced pressure to obtain 13.5 g of an oily substance. The resulting oil was separated and purified by silica gel column chromatography (ethyl acetate / hexane 1:5) to obtain...
Embodiment 2
[0051] Synthesis Example 2 (Synthesis Example of Glucose Isobutyrate Derivatives)
[0052] Except that anhydrous isobutyric acid was used instead of anhydrous isovaleric acid, 3.5 g of glucose-1,2,3,4,6-penta-O-isobutyric acid was synthesized, isolated and purified in the same manner as in Synthesis Example 1 Ester (Rf=0.80, Yield: 27.5%), 0.4g Glucose-1,2,3,4-Tetra-O-isobutyrate (Rf=0.70, Yield: 27.0%), 2.7g Glucose -1,2,4,6-tetra-O-isobutyrate (Rf=0.68, yield: 23.0%), 0.61g glucose 1,2,3,6-tetra-O-isobutyrate ( Rf = 0.73, yield: 27.0%), 0.59 g of glucose-1,3,6-tri-O-isobutyrate (Rf = 0.65, yield: 5.0%).
[0053] The glucose isobutyrate derivative obtained above was identified by the same method as in Synthesis Example 1.
[0054] Glucose-1,2,3,4,6-penta-O-isobutyrate
[0055] FAB mass: 558[M+Na] +
[0056] H-NMR (δ, CDCl 3 ): 6.33 (1H, d, J3.7 1-H), 5.49 (1Ht, J9.5, 3-H), 5.13 (1H, t, J9.9, 4-H), 5.06 (1H, dd, J9.9 and 3.7, 2-H), 4.12 (2H, m, 6-H), 4.06 (1H, m, 5-H), ...
Embodiment 3
[0069] Synthesis Example 3 (Synthesis Example of Sucrose Isovalerate Derivatives)
[0070] Sucrose was used instead of glucose, the stirring temperature was changed to 80° C., and other processes were the same as in Synthesis Example 1 to obtain 12.3 g of oil. The resulting oil was separated and purified by silica gel column chromatography (ethyl acetate / hexane 1:6) to obtain: 2.3 g of sucrose-2,3,4,7,8,10,11,12-octa-O-isoamyl Ester (Rf=0.83, yield: 15.8%), 1.8 g sucrose-2,4,7,8,10,11,12-hepta-O-isovalerate (Rf=0.70, yield: 13.4%) ), 1.3 g of sucrose-3,7,8,10,11,12-hexa-O-isovalerate (Rf=0.62, yield: 10.6%).
[0071] The sucrose isovalerate derivative obtained above was identified by the same method as in Synthesis Example 1.
[0072] Sucrose-2,3,4,7,8,10,11,12-octa-O-isovalerate
[0073] FAB mass: 1014[M+Na] +
[0074] H-NMR (δ, CDCl 3 ): 5.46 (1H, m, 5-H), 5.42 (1H, d, J3.9, 7-H), 5.35 (1H, t, J8, 8-H), 4.83 (1H, t, J9.9 , 2-H), 4.80(1H, m, 4-H), 4.51(1H, t, J9.9, 3-H...
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