A New Tri-atomic Alcohol from the Urine of Pregnant Women.

A new alcohol differing from the pregnandiol of Marrian and Butenandt and also from the crystalline ovarian hormone isolated by Doisy, Thayer and Veler, Butenandt, Laquer and Marrian has been obtained from the urine of pregnant women. This alcohol has been isolated in the form of snow white crystals. The melting point by the open beaker method of 5 different preparations was 273°, 273°, 273°, 272.3°, 272° (uncorrected). The crystals melted sharply without decomposition. The molecular weight determination by Rast's micro procedure gave an average value of 294. The iodine numbers of 3 different preparations were 85.3, 86.2, and 88.5. The average of these values, 86.7, permits one to calculate a molecular weight of 292.8 if one double bond is assumed. Determination of the number of hydroxyls in 2 samples by the procedure of Peterson and West indicates that 3 atoms of oxygen exist in this form. Found 124, 129; theory 129 gms. of CH3C = 0 per mole. The average molecular weight of the triacetyl derivative is 410. M. P. 126° uncorrected. The specific rotation of a 0.322% solution in 95% ethyl alcohol at 28° in a 2 dm. tube with a sodium flame was +68.3°. Another sample (0.148%) gave a value of +72.8°. Qualitative analysis did not detect sulfur, halogens or nitrogen. Quantitative micro analysis: carbon 75.15%; hydrogen 8.22%. Calculated for C18H24O3, carbon 74.95%; hydrogen 8.39%; mol. wt. 288.