An Improved Method of Preparing Testosterone, Dihydrotestosterone and Some of their Esters

Ercoli, A; Ruggieri, Pietro

doi:10.1021/ja01099a040

Cited by 35 publications

(8 citation statements)

References 4 publications

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“…The distribution of the sterol in brains from different mammals has not been widely examined. The presence of cholest-5-ene-3flY24-diol in equine brain ERCOLI and DE RUGGIERI, 1953b;FIESER et al, 1957) and human brain (DI FRISCO et al, 1953;ERCOLI and DE RUGGIERI, 1953u,b) was established early, but its presence in bovine brain DI FRISCO et al, 1953;FIESER et al, 1957) remained uncertain until very recently (RICHTER and DANNENBERG, 1969). The presence of cholest-5-ene-3flY24diol in rabbit brain likewise has been uncertain (RICHTER and DANNENBERG, 1969).…”

Section: Discussionmentioning

confidence: 99%

BIOSYNTHESIS OF CHOLEST‐5‐ENE‐3β, 24‐DIOL (CEREBROSTEROL) BY BOVINE CEREBRAL CORTICAL MICROSOMES¹

Dhar

Teng

Smith

1973

Journal of Neurochemistry

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The presence of cholest‐5‐ene‐3β, 24‐diol (cerebrosterol) in samples of human, bovine, and rabbit brains has been established by isolation of the sterol therefrom and identification by comparison of physical properties. Cholest‐5‐ene‐3β, 24‐diol was present at the level of 66.5 sg/g of dried tissue in human brain, 42.9 μg/g in cattle brain, and 89.5 pg/g in rabbit brain. Cholest‐5‐ene‐3β, 24‐diol was the only readily detectable hydroxycholesterol derivative in these brain tissues and was concentrated in the 105,000 g pellet (microsomal fraction) of both human and bovine cerebral cortex, with no demonstrable amounts of the sterol present in nuclear or mitochondrial fractions. Incubation of [1,2‐3H]‐ or of [4‐14C]‐cholesterol with the 105,000 g microsomal pellet from bovine cerebral cortical homogenates demonstrated 0.1‐0.38 per cent conversions to radioactive cholest‐5‐ene‐3β, 24‐diol, isolated and purified as the 3β, 24‐dibenzoate. The bioconversion required oxygen, and a stimulation of hydroxylation by added NADPH2 was demonstrated. Our observations establish that a sterol 24‐hydroxylase system is present in bovine cerebral cortex.

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Section: Discussionmentioning

confidence: 99%

BIOSYNTHESIS OF CHOLEST‐5‐ENE‐3β, 24‐DIOL (CEREBROSTEROL) BY BOVINE CEREBRAL CORTICAL MICROSOMES¹

Dhar

Teng

Smith

1973

Journal of Neurochemistry

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“…The preparation of the cyanohydrin (II), based on the method of Ercoli & Ruggieri (1953), with acetone cyanohydrin was found to be the most efficient (cf. Velluz & Muller, 1950;Goldberg & Studer, 1941 a, b).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 3-hydroxy-19-nor[21-14C]pregna-1,3,5(10)-trien-20-one from [14C]methyl iodide

Schulster¹,

Whitehead²,

Kellie³

1964

Biochemical Journal

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“…Thus the 17-monocyanohydrins of steroidal 3,17-diones are prepared in practically quantitative yield (eq 3). 6 Similarly, α-silyloxynitriles are prepared from O-trimethylsilylated acetone cyanohydrin by transcyanosilylation 7 in the presence of Potassium Cyanide and 18-Crown-6.…”

Section: N-buchomentioning

confidence: 99%

Acetone Cyanohydrin

Haroutounian¹

2001

Encyclopedia of Reagents for Organic Synthesis

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An Improved Method of Preparing Testosterone, Dihydrotestosterone and Some of their Esters

Cited by 35 publications

References 4 publications

BIOSYNTHESIS OF CHOLEST‐5‐ENE‐3β, 24‐DIOL (CEREBROSTEROL) BY BOVINE CEREBRAL CORTICAL MICROSOMES¹

BIOSYNTHESIS OF CHOLEST‐5‐ENE‐3β, 24‐DIOL (CEREBROSTEROL) BY BOVINE CEREBRAL CORTICAL MICROSOMES¹

Synthesis of 3-hydroxy-19-nor[21-14C]pregna-1,3,5(10)-trien-20-one from [14C]methyl iodide

Acetone Cyanohydrin

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An Improved Method of Preparing Testosterone, Dihydrotestosterone and Some of their Esters

Cited by 35 publications

References 4 publications

BIOSYNTHESIS OF CHOLEST‐5‐ENE‐3β, 24‐DIOL (CEREBROSTEROL) BY BOVINE CEREBRAL CORTICAL MICROSOMES1

BIOSYNTHESIS OF CHOLEST‐5‐ENE‐3β, 24‐DIOL (CEREBROSTEROL) BY BOVINE CEREBRAL CORTICAL MICROSOMES1

Synthesis of 3-hydroxy-19-nor[21-14C]pregna-1,3,5(10)-trien-20-one from [14C]methyl iodide

Acetone Cyanohydrin

Contact Info

Product

Resources

About

BIOSYNTHESIS OF CHOLEST‐5‐ENE‐3β, 24‐DIOL (CEREBROSTEROL) BY BOVINE CEREBRAL CORTICAL MICROSOMES¹

BIOSYNTHESIS OF CHOLEST‐5‐ENE‐3β, 24‐DIOL (CEREBROSTEROL) BY BOVINE CEREBRAL CORTICAL MICROSOMES¹