Über physikalische und chemische Eigenschaften des krystallisierten Follikelhormons. Untersuchungen über das weibliche Sexualhormon. (5. Mitteilung.)

Abstract

The pure follicular hormone, characterized by melting point, crystalline form, solubility, optical rotation, ultraviolet absorption spectrum and physiological action, has, according to previous determinations, as its probable formula C18H22O2; this formula needed further confirmation, since the homologous formula C17H20O2 appeared according to former researches not completely excluded, though much less probable. The relations of the O atoms could be verified. One is present as an easily esterifiable hy-droxyl group, as could be shown by the preparation of acetyl and benzoyl derivatives; the other O atom is in a carbonyl group, which gives a test with ketone reagents. The hormone therefore has the structure of a hydroxyketone; it is probable that the transformation of the neutral substance into an alkali-soluble form (a reaction that corresponds to that of a lactone) is to be explained by a ready transformation of the carbonyl group into an enol group. The molecule probably contains 3 double bonds. These are saturated by intensive hydrogenation with simultaneous reduction of the keto group. The hydrocarbon C18H30 is the foundation for the completely hydrogenated hormone C18H30O. It contains 8 fewer H atoms than a saturated paraffin, a fact that can be explained by the presence of either an aromatic nucleus or of 4 hydrogenated rings in the molecule.