反应详情

Retinoyl fluoride (2.4 g) was dissolved in 300 ml of acetone. D-Glucuronic acid (6 g) dissolved in 75 ml of water and sodium bicarbonate (6 g) dissolved in 75 ml of water were added to the retinoyl fluoride solution. The mixture was stirred at room temp. for 12-16 hours. More water (100-150 ml) was added and the stirring was continued for 8-12 hours more until most of the retinoyl fluoride had reacted. The solution was diluted with water, acidified with 1N HCl, and the product was extracted with n-butanol. The extract was washed with water, dried over anhydrous sodium sulfate and then evaporated to dryness in a rotary evaporator. The residue was dissolved in 2-3 ml of diethyl ether and transferred to a silica gel (for dry column chromatography, wet packed with hexane) column. The column was developed with hexane containing diethyl ether (5-50%) to remove retinoic acid and other products. The major yellow band containing retinoyl glucuronide was next eluted with a mixture of CH2Cl2 /CH3OH (1:1). The solvent was evaporated to dryness to give solid retinoyl glucuronide (2.1 g, 60%).

1. waitthe stirring was continued for 8-12 hours
2. extractionthe product was extracted with n-butanol
3. washThe extract was washed with water
4. dry with materialdried over anhydrous sodium sulfate
5. customevaporated to dryness in a rotary evaporator
6. dissolutionThe residue was dissolved in 2-3 ml of diethyl ether
7. additioncontaining diethyl ether (5-50%)
8. customto remove retinoic acid and other products
9. additionThe major yellow band containing retinoyl glucuronide
10. washwas next eluted with a mixture of CH2Cl2 /CH3OH (1:1)
11. customThe solvent was evaporated to dryness