Progesterone testosterone mixture

Fast, D.M. Culbreth, P.H. Sampson, E.J. Multivariate and univariate optimization studies of liquid-chromatographic separation of steroid mixtures. Clin.Chem., 1982, 28, 444-448 [also estriol, hydrocortisone, progesterone, testosterone]... 

Fig. 2 Fluorescence scan of a J -S-ketosteroid mixture after INH treatment. Aldosterone (1), corticosterone (2), cortexolone (3), testosterone (4), progesterone (5).

The addition of bromine and chlorine azide to unsaturated steroids is generally diastereoselective, when both the simple and induced diastereoselectivity are considered. In fact, a single enantiomer was obtained from 5a-cholest-2-ene (8)35,36, cholesterol (9)51, and progesterone (10)52 (in this case with undetermined configuration). Testosterone esters, however, afforded mixtures of stereoisomers52. 

Figure 4 Chromatogram of a mixture of eight steroids. Chromatographic systems (A) ODS-2/0.12moll SDS/6% (v/v) 1-pentanol, and (B) ODS-2/52% (v/v) acetonitrile. Compounds (1) dehydrotestosterone, (2) testosterone, (3) methyltestoster-one, (4) medroxyprogesterone acetate, (5) dydrogesterone, (6) progesterone, (7) testosterone propionate, and (8) nandro-ione.

Geometrical isomeric mixtures of steroidal oxime esters have been evaluated for the enzymatic transformations. In this respect, the work by Adamczyk and co-workers [27] describes the use of lipase from CCL in the diastereoselective hydrolysis of 3-(0-carbox-ymethyl)oxime methyl esters, 17a-hydroxyprogesterone 122, progesterone 124, testosterone 126, and cortisol 128. CCL proved to be effective in carrying out hydrolysis of methyl esters of steroidal 3-carboxymethyl oximes in a mild manner affording the E and Z dia-stereoisomers 123/122, 125/124, 127/126, and 129/128 in different ratios. The enzyme exhibited a preference for the anti isomer (Table 11). The faster rate and greater selectivity observed for 128 is probably due to the cortisol derivative s better solubility in the reaction media. 

---