Testosterone derivatives, comparison

Halogenated acyl derivatives of steroids have been applied in order to increase sensitivity of the analysis. It follows from a comparison of the ECD responses of haloacetates of steroids that the highest sensitivity can be obtained with the aid of monochloro-acetates [351]. Brownie et al. [352] applied them in the analysis of testosterone in blood. The method involves the extraction of blood plasma with diethyl ether, purification by TLC and derivatization. GC analysis is performed only after a preliminary separation on a thin layer. Preparation of the derivatives is carried out by treating a dried extract with... 

Comparison of various halogenated acyl derivatives verifies that the typical properties of the ECD apply also for steroids [355]. Table 5.13 compares the relative retention times and responses of different derivatives of testosterone and cholesterol obtained on... 

COMPARISON OF RELATIVE RETENTIONS AND FID AND ECD RESPONSES OF TESTOSTERONE AND CHOLESTEROL HALOGENATED ACYL DERIVATIVES [355]... 

Hexadecafluorononanoates and eicosafluoroundecanoates of testosterone and estradiol were chromatographed by Kirschner and Taylor [363]. In comparison with HFB derivatives, they have longer retention times and the area responses are 2—2.5 time higher for the di-derivatives the difference in responses is very small. 

Collection of the GC effluent and subsequent MS analysis allowed assignment of a possible molecular formula as Ci9H280. Since boar taint can be eliminated by castration of male pigs, attention was focused on the testosterone and androsterone family of compounds as possible candidates. When the crude volatiles were treated with 2,4-dinitrophenylhydrazine, the boar taint odor was completely removed, implicating a ketone functionality for the lone oxygen atom. Anecdotal information implicated several androstene derivatives, including 47, which was described as having an intense, urine-like odor. 143 An authentic sample of 47 was prepared, and comparison of the GC and MS properties allowed the definitive structural identification of the boar taint compound. 

Fig. 7 Comparison of the binding constants of hydrophobic steroids, testosterone, and progesterone with P-CD and anionic P-CD derivatives. SA Sulfonate anion at the 6-position, SPE Anionic sulfopropyl ether substituent and SBE Anionic sulfobutyl ether substituent. (Adapted from Ref...

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