Abstract
No doubt the possibility of preparing prolan, theelin and theelol from the same urine has occurred to many investigators interested in sex hormones. In this note we have given the adaptation of processes published from this laboratory which permits the preparation of the 3 substances. The combined methods which have been in constant use for about one year give a satisfactory yield of all 3 compounds.
The prolan is made by the benzoic acid process described by Katzman and Doisy. 1 The filtered urine is strongly acidified with hydrochloric acid and after a few days the supernatant liquid siphoned from the precipitate. The urine is extracted with butyl alcohol in the continuous extraction apparatus (Veler, Thayer and Doisy 2 ). The solvent is distilled off, the residue leached with benzene and the benzene removed by distillation. The residue from 100 gallons of urine is dissolved in 1500 cc. of 80% ethyl alcohol containing 150 cc. of concentrated hydrochloric acid. The solution is hydrolyzed by boiling for 4 hours, the alcohol removed by distillation and solid NaOH added until the solution is alkaline to phenolphthalein. The solution is transferred to separatory funnels and extracted with butyl alcohol to which an equal volume of petroleum ether is added. The butyl alcohol-petroleum ether solution of theelin and theelol are then worked up according to the process described by Doisy and Thayer 3 beginning, however, at Step 3. We have found that the purification of theelol as the sodium salt (MacCorquodale, Thayer and Doisy 4 ) to be quite advantageous.
Though we have no quantitative data on the yield of theelin, the recovery seems to be quite satisfactory. The yield of theelol has ranged from 2 to 5 mg. per gallon of urine.
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