Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol
This paper describes syntheses of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol which give higher yields than previously published methods. In addition, 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol was synthesized by a different procedure, namely via performic acid...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
1976-01-01
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| Series: | Journal of Lipid Research |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S002222752037019X |
| _version_ | 1819055505147953152 |
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| author | B Dayal S Shefer G S Tint G Salen E H Mosbach |
| author_facet | B Dayal S Shefer G S Tint G Salen E H Mosbach |
| author_sort | B Dayal |
| collection | DOAJ |
| description | This paper describes syntheses of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol which give higher yields than previously published methods. In addition, 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol was synthesized by a different procedure, namely via performic acid oxidation of the correspinding unsaturated triol, which gave a lower yield but avoided the formation of 5β-cholestane-3α, 7α, 12α, 25, 26-pentol, which normally tends to contaminate the final product. Structures were confirmed by gas-liquid chromatography, infrared-, proton magnetic resonance- and mass spectrometry, 5β-Cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol were required for in vivo and in vitro studies of the (hypothetical) 25-hydroxylation pathway of cholic acid biosynthesis.Patients with the rare familial sterol storage disease, cerebrotendinous xanthomatosis (CTX) (1), secrete a number of C27 bile alcohols in bile and feces (2). One of the main components of the bile alcohol fraction was a tetrahydroxy bile alcohol, 5β-cholestane-3α,7α,12α,25-tetrol. A pentnhydroxy bile alcohol fraction consisted of two major and several minor components (3). One of the pentahydroxy bile alcohols was 5β-cholestane-3α7α,12α,24α,25-pentoiln dicating that in CTX subjects there existed a pathway of bile acid synthesis involving 25-hydroxylated intermediates, rather than 26-hydroxylated compounds, as previously reported for normal subjects.In order to investigate individual biochemical steps of the 25-hydroxylation pathway of cholic acid biosynthesis, it was necessary to prepare C27 bile alcohol derivatives, substituted in the 25-position. This paper describes the synthesis of 5β-cholestane-3α,7α,12α,25-tetrola nd 5β-cholestane-3α,7α,12α,- 24ξ,25-pentol from cholic acid. Certain modifications of the published procedures were required to improve the yield and purity of these substances. |
| first_indexed | 2024-12-21T13:08:35Z |
| format | Article |
| id | doaj.art-15eee089cb224b7882f7afb747f2d82f |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-21T13:08:35Z |
| publishDate | 1976-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-15eee089cb224b7882f7afb747f2d82f2022-12-21T19:02:57ZengElsevierJournal of Lipid Research0022-22751976-01-011717477Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentolB Dayal0S Shefer1G S Tint2G Salen3E H Mosbach4Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016; Veterans Administration Hospital, Eat Orange, N.J. 07019Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016; Veterans Administration Hospital, Eat Orange, N.J. 07019Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016; Veterans Administration Hospital, Eat Orange, N.J. 07019Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016; Veterans Administration Hospital, Eat Orange, N.J. 07019Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016; Veterans Administration Hospital, Eat Orange, N.J. 07019This paper describes syntheses of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol which give higher yields than previously published methods. In addition, 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol was synthesized by a different procedure, namely via performic acid oxidation of the correspinding unsaturated triol, which gave a lower yield but avoided the formation of 5β-cholestane-3α, 7α, 12α, 25, 26-pentol, which normally tends to contaminate the final product. Structures were confirmed by gas-liquid chromatography, infrared-, proton magnetic resonance- and mass spectrometry, 5β-Cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol were required for in vivo and in vitro studies of the (hypothetical) 25-hydroxylation pathway of cholic acid biosynthesis.Patients with the rare familial sterol storage disease, cerebrotendinous xanthomatosis (CTX) (1), secrete a number of C27 bile alcohols in bile and feces (2). One of the main components of the bile alcohol fraction was a tetrahydroxy bile alcohol, 5β-cholestane-3α,7α,12α,25-tetrol. A pentnhydroxy bile alcohol fraction consisted of two major and several minor components (3). One of the pentahydroxy bile alcohols was 5β-cholestane-3α7α,12α,24α,25-pentoiln dicating that in CTX subjects there existed a pathway of bile acid synthesis involving 25-hydroxylated intermediates, rather than 26-hydroxylated compounds, as previously reported for normal subjects.In order to investigate individual biochemical steps of the 25-hydroxylation pathway of cholic acid biosynthesis, it was necessary to prepare C27 bile alcohol derivatives, substituted in the 25-position. This paper describes the synthesis of 5β-cholestane-3α,7α,12α,25-tetrola nd 5β-cholestane-3α,7α,12α,- 24ξ,25-pentol from cholic acid. Certain modifications of the published procedures were required to improve the yield and purity of these substances.http://www.sciencedirect.com/science/article/pii/S002222752037019X |
| spellingShingle | B Dayal S Shefer G S Tint G Salen E H Mosbach Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol Journal of Lipid Research |
| title | Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol |
| title_full | Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol |
| title_fullStr | Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol |
| title_full_unstemmed | Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol |
| title_short | Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol |
| title_sort | synthesis of 5β cholestane 3α 7α 12α 25 tetrol and 5β cholestane 3α 7α 12α 24ξ 25 pentol |
| url | http://www.sciencedirect.com/science/article/pii/S002222752037019X |
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