Estradurin, Ayerst, US ,1957
3 g of estradiol was dissolved in 75 ml of anhydrous pyridine. The solution was cooled to -10°C, whereupon a solution of 1.1 ml of phosphorus oxychloride in 10 ml of anhydrous pyridine was added with agitation. After the addition, which required 7 minutes, the reaction mixture was kept at -10°C for a further period of 3 hours, and then it was left standing at room temperature for 15 hours. A clear solution thus resulted, to which finely crushed ice was then added. The resulting solution was evaporated in vacuum to dryness. After drying in a vacuum desiccator, 3.8 g of a white powder was obtained. This powder was suspended in 2 ml of pyridine, and 25 ml of 0.5 N sodium hydroxide was added, whereupon a solution was obtained which was then diluted with water to 100 ml.
The solution was then dialyzed through a cellophane membrane against 4 liters of water for 10 hours, with stirring. The dialysis was repeated 2 additional times, with fresh amounts of water. To the dialyzed solution there was added 2 ml of 1 N hydrochloric acid, whereupon polyestradiol phosphatewas precipitated as a white bulky precipitate. This was centrifuged off and washed repeatedly with 0.1 N hydrochloric acid. Thereafter it was dried in a vacuum desiccator. The yield was 3 g of polyestradiol phosphate. The analysis shows 0.65% of water, 1.35% of pyridine and 9.3% of phosphorus (calculated on a dry sample).
Confirmed carcinogen
producing liver tumors. An experimental
teratogen. A drug used in cancer treatment.
When heated to decomposition it emits
toxic fumes of POx. See also ESTRADIOL,
ESTERS, POLYMERS, and
PHOSPHORIC ACID.
