Determination of Δ4-3-ketosteroids based on oxime formation by difference circular dichroism spectroscopy

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Abstract

Δ4-3-Ketosteroids exhibit an intensive negative Cotton effect on the circular dichroism (CD) spectra in the wavelength range for the n-pi;* electronic transition (270-350 nm). With hydroxylamine hydrochloride, Δ4-3-ketosteroid compounds can be transformed into oxime derivatives. Following oxime formation, positive ellipticity with low intensity can be registered in this wavelength range. The quantitative determination of Δ4-3-ketosteroids is based on the considerable difference between the ellipticities before and after oxime formation. The difference ellipticity for the six ketosteroids examined (norethisterone, levonorgestrel, levonorgestrel acetate, methyltestosterone, testosterone phenylpropionate, nortestosterone phenylpropionate) varies linearly with the concentration in the interval 6 × 10-6-3 × 10-3 mol/L. The method can be well applied to determination of Δ4-3-ketosteroid contamination of norgestimate [(+)-13-ethyl-17-hydroxy-18,19-dinor-17α-pregn4-en-20-yn-3-one oxime acetate]; 0.02-10% impurity can be measured.

Original languageEnglish
Pages (from-to)384-388
Number of pages5
JournalFresenius' journal of analytical chemistry
Volume368
Issue number4
Publication statusPublished - 2000

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Ketosteroids
Circular dichroism spectroscopy
Oximes
Circular Dichroism
Spectrum Analysis
Levonorgestrel
Acetates
Methyltestosterone
Norethindrone
Wavelength
Hydroxylamine
Cotton
Contamination
Impurities
Derivatives

ASJC Scopus subject areas

  • Biochemistry

Cite this

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title = "Determination of Δ4-3-ketosteroids based on oxime formation by difference circular dichroism spectroscopy",
abstract = "Δ4-3-Ketosteroids exhibit an intensive negative Cotton effect on the circular dichroism (CD) spectra in the wavelength range for the n-pi;* electronic transition (270-350 nm). With hydroxylamine hydrochloride, Δ4-3-ketosteroid compounds can be transformed into oxime derivatives. Following oxime formation, positive ellipticity with low intensity can be registered in this wavelength range. The quantitative determination of Δ4-3-ketosteroids is based on the considerable difference between the ellipticities before and after oxime formation. The difference ellipticity for the six ketosteroids examined (norethisterone, levonorgestrel, levonorgestrel acetate, methyltestosterone, testosterone phenylpropionate, nortestosterone phenylpropionate) varies linearly with the concentration in the interval 6 × 10-6-3 × 10-3 mol/L. The method can be well applied to determination of Δ4-3-ketosteroid contamination of norgestimate [(+)-13-ethyl-17-hydroxy-18,19-dinor-17α-pregn4-en-20-yn-3-one oxime acetate]; 0.02-10{\%} impurity can be measured.",
author = "A. Szentesi and A. Gergely and P. Horv{\'a}th and G. Sz{\'a}sz",
year = "2000",
language = "English",
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pages = "384--388",
journal = "Fresenius Zeitschrift fur Analytische Chemie",
issn = "1618-2642",
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T1 - Determination of Δ4-3-ketosteroids based on oxime formation by difference circular dichroism spectroscopy

AU - Szentesi, A.

AU - Gergely, A.

AU - Horváth, P.

AU - Szász, G.

PY - 2000

Y1 - 2000

N2 - Δ4-3-Ketosteroids exhibit an intensive negative Cotton effect on the circular dichroism (CD) spectra in the wavelength range for the n-pi;* electronic transition (270-350 nm). With hydroxylamine hydrochloride, Δ4-3-ketosteroid compounds can be transformed into oxime derivatives. Following oxime formation, positive ellipticity with low intensity can be registered in this wavelength range. The quantitative determination of Δ4-3-ketosteroids is based on the considerable difference between the ellipticities before and after oxime formation. The difference ellipticity for the six ketosteroids examined (norethisterone, levonorgestrel, levonorgestrel acetate, methyltestosterone, testosterone phenylpropionate, nortestosterone phenylpropionate) varies linearly with the concentration in the interval 6 × 10-6-3 × 10-3 mol/L. The method can be well applied to determination of Δ4-3-ketosteroid contamination of norgestimate [(+)-13-ethyl-17-hydroxy-18,19-dinor-17α-pregn4-en-20-yn-3-one oxime acetate]; 0.02-10% impurity can be measured.

AB - Δ4-3-Ketosteroids exhibit an intensive negative Cotton effect on the circular dichroism (CD) spectra in the wavelength range for the n-pi;* electronic transition (270-350 nm). With hydroxylamine hydrochloride, Δ4-3-ketosteroid compounds can be transformed into oxime derivatives. Following oxime formation, positive ellipticity with low intensity can be registered in this wavelength range. The quantitative determination of Δ4-3-ketosteroids is based on the considerable difference between the ellipticities before and after oxime formation. The difference ellipticity for the six ketosteroids examined (norethisterone, levonorgestrel, levonorgestrel acetate, methyltestosterone, testosterone phenylpropionate, nortestosterone phenylpropionate) varies linearly with the concentration in the interval 6 × 10-6-3 × 10-3 mol/L. The method can be well applied to determination of Δ4-3-ketosteroid contamination of norgestimate [(+)-13-ethyl-17-hydroxy-18,19-dinor-17α-pregn4-en-20-yn-3-one oxime acetate]; 0.02-10% impurity can be measured.

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