1807-02-9

Basic information

• Product Name: 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one
• Synonyms: 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one;11#-HYDROXYMETHYLTESTOSTERONE;11α,17β-Dihydroxy-17-methylandrost-4-en-3-one;11α-Hydroxy-17-methyltestosterone;(11α,17β)-11,17-dihydroxy-17-methylandrost-4-en-3-one;(8S,9S,10R,11R,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one;(8S,9S,10R,11R,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-1,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthren-3(6H)-one
• CAS NO: 1807-02-9
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.4504
• EINECS: 217-306-7
• Product Categories: Steroids
• Mol File: 1807-02-9.mol

Chemical Properties

• Melting Point: 160-162 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 475.5°Cat760mmHg
• Flash Point: 255.5°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 4.87E-11mmHg at 25°C
• Refractive Index: 1.573
• PKA: 14.57±0.70(Predicted)
• CAS DataBase Reference: 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one(1807-02-9)
• EPA Substance Registry System: 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one(1807-02-9)

Safety Data

• Hazardous Substances Data: 1807-02-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one is used as a pharmaceutical agent for its glucocorticoid activity. The expression is: 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one is used as a glucocorticoid hormone for its role in modulating the immune system and anti-inflammatory effects.
Used in Research Applications:
In the field of research, 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one is used as a research tool for studying the effects of glucocorticoids on cellular processes and the role of zinc uptake in various biological functions. The expression is: 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one is used as a research compound for investigating the mechanisms of glucocorticoid action and zinc homeostasis in cells.
Used in Endocrinology:
11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one is also used in endocrinology to understand the role of adrenal steroid hormones in the regulation of various physiological processes. The expression is: 11alpha,17beta-dihydroxy-17-methylandrost-4-en-3-one is used as an endocrine hormone for studying the effects of adrenal steroid hormones on the body's metabolic and immune responses.

InChI:InChI=1/C20H30O3/c1-18-8-6-13(21)10-12(18)4-5-14-15-7-9-20(3,23)19(15,2)11-16(22)17(14)18/h10,14-17,22-23H,4-9,11H2,1-3H3

Upstream product

• 58-18-4 17-methyltestosterone 

Downstream Products

• 5419-48-7 17β-hydroxy-17α-methyl-androst-4-ene-3,11-dione 
• 1039-17-4 Δ⁹⁽¹¹⁾-methyltestosterone 

Relevant articles and documents

Application of α- and β-naphthoflavones as monooxygenase inhibitors of Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651 in transformation of 17α-methyltestosterone

In this work, 17α-methyltestosterone was effectively hydroxylated by Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651. A. coerulea KCh 93 afforded 6β-, 12β-, 7α-, 11α-, 15α-hydroxy derivatives with 44%, 29%, 6%, 5% and 9% yields, respectively. S. racemosum KCh 105 afforded 7α-, 15α- and 11α-hydroxy derivatives with yields of 45%, 19% and 17%, respectively. Chaetomium sp. KCh 6651 afforded 15α-, 11α-, 7α-, 6β-, 9α-, 14α-hydroxy and 6β,14α-dihydroxy derivatives with yields of 31%, 20%, 16%, 7%, 5%, 7% and 4%, respectively. 14α-Hydroxy and 6β,14α-dihydroxy derivatives were determined as new compounds. Effect of various sources of nitrogen and carbon in the media on biotransformations were tested, however did not affect the degree of substrate conversion or the composition of the products formed. The addition of α- or β-naphthoflavones inhibited 17α-methyltestosterone hydroxylation but did not change the percentage composition of the resulting products.

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.