Optical-Analytical Studies on Steroids

Meyer, A. S.; Lindberg, Marjorie C.

doi:10.1021/ac60101a035

Cited by 33 publications

(16 citation statements)

References 21 publications

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“…The correlation coefficient was greater than 0.95 in all cases. IV + VI = From these data and from previous observations (18,19), the reactivity of the corticosteroids toward I appears to be, in part, a function of their molecular shape. Steroids with C-16 substitution in either the a-or 8-position react the slowest, steroids that possess a planar A ring and have sp3 C-11 substitution show intermediate reactivity, and steroids possessing a C-11 carbonyl react the fastest with I.…”

Section: Resultssupporting

confidence: 67%

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Kinetics and Mechanism of Blue Tétrazolium Reaction with Corticosteroids

Oteiza

Wooten

Kenner

et al. 1977

Journal of Pharmaceutical Sciences

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Section: Resultssupporting

confidence: 67%

“…Significant variations in the reaction rates of corticosteroids of closely related structures also were noted (1,9,14,15,18,19). The reaction rate of corticosteroids with I was inversely related t o the dielectric constant of the solvating media in another study (20), and it was established that the a-carbonyl moiety of the corticosteroid reduces I (18).…”

mentioning

confidence: 93%

Kinetics and Mechanism of Blue Tétrazolium Reaction with Corticosteroids

Oteiza

Wooten

Kenner

et al. 1977

Journal of Pharmaceutical Sciences

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“…However, the more rapid shift of the A4-6a-hydroxyl compounds, which would indicate that such isomerization would occur more easily (cf. 26), was surprising in view of a report (36) that no isomerization was observed nder alkaline conditions when A4-pregnene-6a ,21-diol-3,20-dione diacetate was hydrolyzed. The varied conditions might well explain the difference in result.…”

Section: A4-andpost~ne-3-17-dionlmentioning

confidence: 94%

“…Alteration in spectral absorption of the color products has allowed correlation of certain structural features of these compounds. Some applications have been reported previously (24)(25)(26)(27). * Paper I1 of this series pre-* Incidentally, by this method the presence of a certain impurity was easily detected in a sample, although i t had not been recognized in two paper-chromatographic systems.…”

mentioning

confidence: 97%

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OPTICAL-ANALYTICAL STUDIES ON STEROIDS. I. LIGHT ABSORPTION BETWEEN 230-500 mμ OF α,β-UNSATURATED AND 3,6-DIKETO STEROIDS IN ALKALINE ETHANOL

Meyer¹

1955

J. Org. Chem.

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For the elucidation of structural features of unknown steroids available in minute quantities only, infrared spectrometry has been developed into a most powerful tool. It is possible by its use to determine the types of functional grouping and the number of carbonyls present in the molecule (cf. 1, 2). However, their exact localization is as yet feasible only in a limited number of specific cases. Ultraviolet absorption (cf. 3) and optical rotation measurements (cf. 4) have proved of help in deciding between alternative structural possibilities. The determination of mobilities in paper-chromatographic systems (inter al. 5 ) can render valuable clues toward the establishment of a more accurate structure and, in combination with the concept of conformational analysis (6)) the configuration of certain substituents may be deduced. In addition, oxidative degradations (cf. 7, 8, 9) followed by estimation of the liberated formaldehyde (inter al. 10) and acetaldehyde (11) as well as the Zimmermann chromogen (inter al. 12, 13) can be employed with advantage for the elucidation of side chain structure. The position of a ketone group may be more accurately defined by the ultraviolet spectrum of a derivative such as a phenylhydrazone (inter al. 3, 14, 15). The action of perchloric acid on certain substituted 2 , 4-dinitrophenylhydrazones should produce a bathochromic shift by extension of the conjugated system (cf. 16). The color formed after reaction of steroids with diphenylamine in acidic medium appears to depend on certain structural arrangements (17). A method has been recently devised for the recognition and estimation of A4-3-ketosteroids by measuring the formation of intensely fluorescent substances resulting from alkaline treatment (18,19). On the other hand, absorption spectra in concentrated sulfuric acid (cf. 20, 21)) valuable as they are for the characterization of individual compounds, do not lend themselves for extensive interpretation of structural elements (cf. 22, 23).In the papers presented in this series, an attempt is made to implement the methods enumerated, prompted by the specific need to determine structures of unknown A4-3-ketosteroids isolated in milligram quantities from biological material. In this communication it is desired to report on the changes encountered in the intense absorption of a number of A4-3-ketosteroids upon exposure to alkaline ethanol a t 23 and 60". Of particular interest were A4-3-ketosteroids containing hydroxyl substituents a t various positions and related substances with carbonyl functions. Alteration in spectral absorption of the color products has allowed correlation of certain structural features of these compounds. Some applications have been reported previously (24-27).* Paper I1 of this series pre-* Incidentally, by this method the presence of a certain impurity was easily detected in a sample, although i t had not been recognized in two paper-chromatographic systems. 1240

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Analysis of Steroids in Mixtures Using the Kinetics of Blue Tetrazolium Reduction

Guttman

1966

Journal of Pharmaceutical Sciences

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Optical-Analytical Studies on Steroids

Cited by 33 publications

References 21 publications

Kinetics and Mechanism of Blue Tétrazolium Reaction with Corticosteroids

Kinetics and Mechanism of Blue Tétrazolium Reaction with Corticosteroids

OPTICAL-ANALYTICAL STUDIES ON STEROIDS. I. LIGHT ABSORPTION BETWEEN 230-500 mμ OF α,β-UNSATURATED AND 3,6-DIKETO STEROIDS IN ALKALINE ETHANOL

Analysis of Steroids in Mixtures Using the Kinetics of Blue Tetrazolium Reduction

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