Photoluminescence Studies on Steroidal Substances

Abstract

The literature is briefly reviewed on current fluorimetric methods for the analysis of steroidal substances, The trend in the development of these methods is indicated with particular interest on sensitivity and selectivity, Fluorescence quenching, complex formation with metals, and chemical transformation are briefly investigated in search of selective reaction with substituents on the steroid skeleton, Chemical transformation under controlled conditions is shown to be a promising tool, The application of trichloroacetic acid as a reagent for locating a wide range of steroids on thin layer plates is shown to give a rapid indication of its selectivity and approximate sensitivity. A specific and sensitive fluorimetric method for determination of digoxin in solution and its application to tablet preparations is described. This method based on a reaction with trichloroacetic acid can be used for digoxin determination in the presence of digitoxin, gitoxin and ouabain, Physiological steroids are also shown not to interfere with the reaction under the conditions described, 17oc-methyltestosterone which is readily available and reacts rapidly with trichloroacetic acid on thin layer plates is used in a detailed study of the trichloroacetic acid reaction, A hydro-oxo-phenanthrene is isolated from the reaction.  The structure of the product which has an aromatic ring-C and is dehydrogenated at the C6-C7 is established from its physical properties and a comparison of these with synthetic hydro-oxo-phenanthrene.  A new route to 2, 3, 4, 12~tetrahydro-12-methyl-2-oxophenanthrene is described and some aspects of steroid rearrangement reported. Absorption and fluorescence study of the hydro-oxo-phenanthrene chromophore in polar and non-polar solvents at room temperature is discussed. Fluorescence is shown to be due to enolisation in strongly acidic solvents,