37976-94-6

Basic information

• Product Name: Androst-5-en-17-one, 3-(acetyloxy)-7-hydroxy-, (3beta,7alpha)- (9CI)
• Synonyms: Androst-5-en-17-one, 3-(acetyloxy)-7-hydroxy-, (3beta,7alpha)- (9CI)
• CAS NO: 37976-94-6
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.4605
• Product Categories: STEROID
• Mol File: 37976-94-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Androst-5-en-17-one, 3-(acetyloxy)-7-hydroxy-, (3beta,7alpha)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Androst-5-en-17-one, 3-(acetyloxy)-7-hydroxy-, (3beta,7alpha)- (9CI)(37976-94-6)
• EPA Substance Registry System: Androst-5-en-17-one, 3-(acetyloxy)-7-hydroxy-, (3beta,7alpha)- (9CI)(37976-94-6)

Safety Data

• Hazardous Substances Data: 37976-94-6(Hazardous Substances Data)

Upstream product

• 853-23-6 prasterone acetate 
• 53-43-0 dehydroepiandrosterone 
• 146863-67-4 Acetic acid (3S,8R,9S,10R,13S,14S)-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 23668-18-0 7α-bromo-3β-(acetyloxy)androst-5-en-17-one 
• 1449-61-2 3β-acetoxy-androst-5-en-7,17-dione 

Downstream Products

• 53-00-9 3β,7α-dihydroxyandrost-5-en-17-one 
• 2487-48-1 3β,7α-dihydroxyandrost-5-ene-17-one 

Relevant articles and documents

MnO2/TBHP: A Versatile and User-Friendly Combination of Reagents for the Oxidation of Allylic and Benzylic Methylene Functional Groups

In the presence of activated MnO2, tert-butyl hydroperoxide (TBHP) in CH2Cl2 is able to oxidize the allylic and benzylic methylene groups of different classes of compounds. I describe a one-pot oxidation protocol based on two sequential steps. In the first step, carried out at low temperature, MnO2 catalyses the oxidation of the methylene group. This is followed by a second step where reaction temperature is increased, allowing MnO2 both to catalyse the decomposition of unreacted TBHP and to oxidize allylic alcohols that could possibly be formed. The proposed oxidation procedure is generally applicable, although its efficiency, regioselectivity, and chemoselectivity are strongly dependent on the structure of the substrate. A simple and user-friendly synthetic procedure for the oxidation of allylic and benzylic methylene groups to the corresponding conjugated carbonyl derivatives is described. The proposed oxidation protocol is based on the combined use of MnO2 and tert-butyl hydroperoxide, and is generally applicable.

Ergosteroids II: Biologically active metabolites and synthetic derivatives of dehydroepiandrosterone

An improved procedure for the synthesis of 3β-hydroxyandrost-5-ene- 7,17-dione, a natural metabolite of dehydroepiandrosterone (DHEA) is described. The synthesis and magnetic resonance spectra of several other related steroids are presented. Feeding dehydroepiandrosterone to rats induces enhanced formation of several liver enzymes among which are mitochondrial sn-glycerol 3-phosphate dehydrogenase (GPDH) and cytosolic malic enzyme. The induction of these two enzymes, that complete a thermogenic system in rat liver, was used as an assay to search for derivatives of DHEA that might be more active than the parent steroid. Activity is retained in steroids that are reduced to the corresponding 17β-hydroxy derivative, or hydroxylated at 7α or 7β, and is considerably enhanced when the 17-hydroxy or 17-carbonyl steroid is converted to the 7-oxo derivative. Several derivatives of DHEA did not induce the thermogenic enzymes whereas the corresponding 7-oxo compounds did. Both short and long chain acyl esters of DHEA and of 7-oxo-DHEA are active inducers of the liver enzymes when fed to rats. 7-Oxo-DHEA-3-sulfate is as active as 7-oxo-DHEA or its 3-acetyl ester, whereas DHEA-3-sulfate is much less active than DHEA. Among many steroids tested, those possessing a carbonyl group at position 3, a methyl group at 7, a hydroxyl group at positions 1, 2, 4, 11, or 19, or a saturated B ring, with or without a 4-5 double bond, were inactive.

19-hydroxy steroids. V. 3 ,7 ,19-Trihydroxy-5-androsten-17-one 3,19-diacetate: a potential precursor in the biosynthesis of B-ring unsaturated estrogens.

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