Abstract:
The formation of various compounds upon reaction of 18 hydroxycorticosterone with neutral and acid-added alcohols as well as with acidic aqueous solutions is described. The time course of their formation in such media has been studied. Some of these compounds have been isolated and tentatively identified by paper chromatography employing double isotope techniques and by mass spectrometry. The more polar form has a C-20 hemiketalic structure; the single less polar form obtained upon storage in neutral methanol would be the methylketal at C-20 but the less polar fraction having the same mobility in the Chromatographie system employed, obtained upon reaction with acidic aqueous solutions, seems to be formed by two different dehydration products. © 1978.
Registro:
Documento: |
Artículo
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Título: | Less polar forms and derivatives of 18 hydroxy-corticosterone |
Autor: | Aragones, A.; Gros, E.G.; Lantos, C.P.; Locascio, G.A. |
Filiación: | Laboratorio de Esteroides, Departamento de Química Biológica, Argentina Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Giudad Universitaria, 1428 Buenos Aires, Argentina
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Palabras clave: | 18 hydroxycorticosterone derivative; endocrine system; 18-Hydroxycorticosterone; Butanols; Chemistry; Corticosterone; Ethanol; Hydrochloric Acid; Methanol; Spectrum Analysis, Mass; Water |
Año: | 1978
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Volumen: | 9
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Número: | 2
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Página de inicio: | 175
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Página de fin: | 180
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DOI: |
http://dx.doi.org/10.1016/0022-4731(78)90081-X |
Título revista: | Journal of Steroid Biochemistry
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Título revista abreviado: | J. Steroid Biochem.
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ISSN: | 00224731
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CODEN: | JSTBB
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CAS: | 18-Hydroxycorticosterone, 561-65-9; Butanols; Corticosterone, 50-22-6; Ethanol, 64-17-5; Hydrochloric Acid, 7647-01-0; Methanol, 67-56-1; Water, 7732-18-5
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00224731_v9_n2_p175_Aragones |
Referencias:
- Péron, (1960) Endocrinology, 66, pp. 458-474
- Dominguez, (1965) Steroids Suppl., 2, pp. 29-49
- Levy, Cargill, Cha, Hood, Carlo, (1965) Steroids, 5, pp. 131-146
- Kirk, Rajagopalan, A synthesis of 11?,18,21-trihydroxypregn-4-ene-3,20-dione (?18-hydroxy-corticosterone?) (1976) Journal of the Chemical Society, Chemical Communications, pp. 77-78
- Damasco, Lantos, (1975) J. steroid Biochem., 6, pp. 69-74
- Sandor, Lanthier, (1963) Acta endocr., Copenh., 42, pp. 355-363
- Raman, Ertel, Ungar, (1964) Endocrinology, 74, pp. 865-869
- Roy, Ramirez, Ulick, (1976) J. steroid Biochem., 7, pp. 81-87
- Génard, Palem-Vliers, Denoel, Van Cauwenberge, Eechauten, (1975) J. steroid Biochem., 6, pp. 201-210
- Damasco, Diaz, Lantos, (1976) Gen. comp. Endocr., 29 (2). , Abstract 124
- Bush, (1952) Biochem. J., 50, pp. 370-378
- Aragonés A., Lantos C. P. and Locascio G. A.: Acta physiol. Latinoam. (in press); Kondo, Mitsugi, Tori, Microbiological Synthesis of Aldosterone from Corticosterone (1966) Journal of the American Chemical Society, 87, pp. 4655-4656
- Schmidlin, Wettstein, Synthese Aldosteron-�hnlicher Corticosteroide.d,l-18-Hydroxycorticosteron undd,l-18-Desoxyaldosteron (1961) Helvetica Chimica Acta, 44, pp. 1596-1607
- Schmidlin, Wettstein, �ber 11,18-dioxygenierte Progesterone. �ber Steroide, 161. Mitteilung (1959) Helvetica Chimica Acta, 42, pp. 2636-2645
- Tori, Tomita, Itazaki, Narisada, Nagata, (1963) Chem. Pharm. Bull (Japan), 11, pp. 956-959
Citas:
---------- APA ----------
Aragones, A., Gros, E.G., Lantos, C.P. & Locascio, G.A.
(1978)
. Less polar forms and derivatives of 18 hydroxy-corticosterone. Journal of Steroid Biochemistry, 9(2), 175-180.
http://dx.doi.org/10.1016/0022-4731(78)90081-X---------- CHICAGO ----------
Aragones, A., Gros, E.G., Lantos, C.P., Locascio, G.A.
"Less polar forms and derivatives of 18 hydroxy-corticosterone"
. Journal of Steroid Biochemistry 9, no. 2
(1978) : 175-180.
http://dx.doi.org/10.1016/0022-4731(78)90081-X---------- MLA ----------
Aragones, A., Gros, E.G., Lantos, C.P., Locascio, G.A.
"Less polar forms and derivatives of 18 hydroxy-corticosterone"
. Journal of Steroid Biochemistry, vol. 9, no. 2, 1978, pp. 175-180.
http://dx.doi.org/10.1016/0022-4731(78)90081-X---------- VANCOUVER ----------
Aragones, A., Gros, E.G., Lantos, C.P., Locascio, G.A. Less polar forms and derivatives of 18 hydroxy-corticosterone. J. Steroid Biochem. 1978;9(2):175-180.
http://dx.doi.org/10.1016/0022-4731(78)90081-X