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Testosterone oxime

Oxime derivatization was utilized by Kushnir et al. [44] to improve ESI sensitivity for testosterone measurement. Using a C18 column for separation (3-min run times) and an API 4000 they monitored MRM transitions 304—>124 and 112 for testosterone oxime and 307—>14 and 112 for the d3 internal standard. Within-run and between-run irreproducibility was < 12%. The LOD was 10 pg/ml, allowing accurate measurement of testosterone in women and children. Reference intervals for the steroid in children of different ages and different Tanner stages are given in the publication as well as values for both free and total testosterone. [Pg.563]

A stereoselective synthesis of testosterone (261) was advanced by Fukumoto and co-workers (331), where ring B was joined to the C/D part by an intramolecular nitrile oxide cycloaddition. The key nitrile oxide dipole was generated in situ from oxime 258, which in turn was derived from the optically active tetrahydroin-danone 257. Tetracyclic isoxazoline (259) was obtained as a single stereoisomer... [Pg.450]

In their studies, Kushnir and co-workers [44, 45] found an increase in sensitivity of ESI detection of testosterone and adrenal steroids when they convert carbonyl groups to oximes. The steroid mixture is dissolved in 300 pi of an aqueous hydroxylamine solution (1.5 mol, pH 10), and following heating for 30 min at 90 C the derivatives are extracted with methyl t-butyl ether (2 ml). [Pg.558]

Kushnir et al. [44, 45] also measured 17-hydroxyprogesterone within a profile of four adrenal steroids (detailed in Hormonal Steroid Profiles below). They utilized an oxime derivative to improve ESI sensitivity and carried out analyses on an ABI 4000 instrument. Rauh and co-workers [70] published a method for 17-hydroxyprogesterone with ancillary measurement of androstenedione and testosterone. The mass spectrometer was an ABI 4000 instrument with an APCI source, operated in positive-ion mode and with on-line cartridge sample extraction and column switching. The MRM transitions were as used by other workers (Table 5.3.1)... [Pg.560]

Testosterone-3-(0-carboxymethyl) Oxime. This compound is prepared according to the general method of Erlanger et al. Testosterone dissolved in ethanol is refluxed for 3 hr with a solution of 0-(carboxy-methyl)hydroxylamine in 2 N KOH. The ethanol is then removed by evaporation, water is added, and the mixture is washed with ethyl acetate. The aqueous solution is acidified to pH 2 with hydrochloric acid. The precipitate formed is filtered, washed with water, and recrystallized from ethyl acetate-petroleum ether. [Pg.155]

M. Niwa, N. Watanabe, H. Ochiai, K. Yamashita, Determination of testosterone concentrations in rat plasma using LC-APCI-MS combined with ethyl oxime and acetyl ester derivatization, J. Chromatogr. B, 824 (2005) 258. [Pg.380]

Other cascade sequences have also been observed to occur from the thermolysis of isoxazolines, thereby increasing the utility of the nitrile oxide cycloaddition reaction. For example, in the context of synthesizing testosterone derivatives, Guarna and coworkers reported that the reaction of a nitrile oxide derived from oxime 89 with 76 gave isoxazoline 90 (Scheme 15) (91TL6395). Hydrolysis of the ketal moiety provided cycloadduct 91, which was heated at reflux in DMF to furnish 92 in 30% yield. [Pg.14]

Smith, A.B., 111, Byrne, K.J. Beauchamp, G.K. 1977. Syn- and awr/-phenylacetaldehyde oxime two novel testosterone-dependent mammalian metabolites. J. Chem. Ecol., 3, 309-319. [Pg.98]

The Mexican owners of Syntex recruited after Marker s departure George Rosenkranz. Within two years, Rosenkranz succeeded not only in the large-scale production of progesterone, but he also estabhshed the synthesis of the male sex hormone, testosterone, from yam roots. The synthesis starts from 16-dehydro-pregnenolone acetate, which is converted into its oxime Beckmann rearrangement ofthe latter is followed by hydrolysis and yields 5-androsten-3)3-ol-17-one acetate. [Pg.539]

FIGURE 14.7 Derivatization for ESI-MS/MS. (A) Preparation of the dimethylaminoethylester of dihydroxycholestanoic acid bis acetate. (B) Preparation of aminoethanesulfonate derivative of chenodeoxycholic acid. (C) Formation of sulfate ester of cholesterol. (D) Preparation of oxime of testosterone. [Pg.313]

Reaction with testosterone 3-(0-carboxymethyl)oxime see Adsorption onto DEAE-cellulose 3.2.1.3... [Pg.488]

Biogenetic-like olefinic cyclizations in nitroalkane solvents result in nucleophilic trapping of an intermediary polycyclic vinyl action by the nitroalkane to afford oxime ethersJ The ingenious application of this finding to secure an entry into 17-oxwenated steroids is portrayed in the facile synthesis of testosterone benzoate by Johnson et al. [Pg.262]

Thus, whereas all the authors consider that the wave in acidic medium corresponds to reduction of the protonated oxime, there is some controversy about the nature of the wave in alkaline solutions. Souchay and Ser [61] investigated the division of the wave for some oximes in strongly acidic solutions into two sections of almost equal height. Lund [28] also observed two two-electron waves with the oxime of testosterone propionate electrolysis at the first wave gave testosterone propionate, formed by hydrolysis of the intermediate ketimine, and electrolysis at the second wave gave the corresponding amine. [Pg.52]

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. [Pg.597]


See other pages where Testosterone oxime is mentioned: [Pg.363]    [Pg.79]    [Pg.363]    [Pg.79]    [Pg.180]    [Pg.180]    [Pg.143]    [Pg.557]    [Pg.161]    [Pg.310]    [Pg.1069]    [Pg.101]    [Pg.372]    [Pg.373]    [Pg.627]    [Pg.267]    [Pg.1447]    [Pg.5]    [Pg.246]    [Pg.208]    [Pg.94]    [Pg.84]    [Pg.80]    [Pg.311]    [Pg.174]    [Pg.281]   
See also in sourсe #XX -- [ Pg.313 ]




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