4146-29-6

Basic information

• Product Name: 4-Estren-6beta,17beta-diol-3-one
• Synonyms: Estr-4-en-3-one,6b,17b-dihydroxy- (7CI,8CI); NSC 9718
• CAS NO: 4146-29-6
• Molecular Formula: C₁₈H₂₆O₃
• Molecular Weight: 0
• Mol File: 4146-29-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 484.3°Cat760mmHg
• Flash Point: 260.8°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 2.07E-11mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: 4-Estren-6beta,17beta-diol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Estren-6beta,17beta-diol-3-one(4146-29-6)
• EPA Substance Registry System: 4-Estren-6beta,17beta-diol-3-one(4146-29-6)

Safety Data

• Hazardous Substances Data: 4146-29-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H26O3/c1-18-7-6-12-11-3-2-10(19)8-14(11)16(20)9-13(12)15(18)4-5-17(18)21/h8,11-13,15-17,20-21H,2-7,9H2,1H3/t11-,12-,13-,15+,16-,17+,18+/m1/s1

Upstream product

• 734-32-7 estra-4-ene-3,17-dione 
• 434-22-0 19-nortestosterone 

Relevant articles and documents

Transformations of 4- and 17α-substituted testosterone analogues by Fusarium culmorum

A series of 4- and/or 17α-substituted testosterone analogues has been incubated with the hydroxylating fungus Fusarium culmorum AM282. It was found that 19-norandrostenedione, 19-nortestosterone, 4-methoxytestosterone, 4-methyltestosterone, and 4-chloro-17α-methyltestosterone were hydroxylated exclusively or mainly at the 6β-position. The mixtures of 6β-, 15α-, and 12β- or 11α-monohydroxy derivatives were obtained from 17α-methyltestosterone and 17α-ethyl-19- nortestosterone - the substrates with alkyl group at C-17α. 4-Chlorotestosterone was predominantly hydroxylated at 15α-position, but the reaction was accompanied by the reduction of 4-en-3-one system, which proceeded in the sequence: reduction of ketone to 3β-alcohol and then reduction of the double 4,5 bond. The results obtained indicate an influence of stereoelectronic and steric effects of substitutes on regioselectivity of the hydroxylation of 4-en-3-one steroids by F. culmorum.

Biotransformation of 19-nortestosterone by Aspergillus wentii MRC 200316

Incubation of 19-nortestosterone 1 with Aspergillus wentii MRC 200316 for 5 days afforded 10β-hydroxy-19-nortestosterone 2 (2%), 6β-hydroxy-19- nortestosterone 3 (60%), and 14α-hydroxy-19-nortestosterone 4 (5%).

Biocatalyst mediated production of 6β,11α-dihydroxy derivatives of 4-ene-3-one steroids

Biotransformation of steroids with 4-ene-3-one functionality such as progesterone (I), testosterone (II), 17α-methyltestosterone (III), 4-androstene-3,17-dione (IV) and 19-nortestosterone (V) were studied by using a fungal system belonging to the genera of Mucor (M881). The fungal system efficiently and quantitatively converted these steroids in regio- and stereo-selective manner into corresponding 6β,11α-dihydroxy compounds. Time course experiments suggested that the transformation was initiated by hydroxylation at 6β- or 11α-(10β-hydroxy in case of V) to form monohydroxy derivatives which upon prolonged incubation were converted into corresponding 6β,11α-dihydroxy derivatives. The fermentation studies carried out using 5 L table-top fermentor with substrates (I and II) clearly indicates that 6β,11α-dihydroxy derivatives of steroids with 4-ene-3-one functionality can be produced in large scale by using M881.