382-45-6

Usage

Uses

Used in Pharmaceutical Industry:
Adrenosterone is used as a pharmaceutical agent for its androgenic activity. It is utilized in the development and production of medications that target hormonal imbalances and conditions related to androgen levels.
Used in Sports and Fitness Industry:
Adrenosterone is used as a performance-enhancing substance for its androgenic effects. It is taken by athletes and bodybuilders to improve muscle mass, strength, and overall performance, although its use may be controversial and subject to regulations.
Used in Research and Development:
Adrenosterone is used as a research compound for studying the effects of androgens on the human body. It aids scientists in understanding the role of androgens in various physiological processes and the development of new drugs and therapies targeting androgen-related conditions.
Used in Veterinary Medicine:
Adrenosterone is used as a veterinary drug for treating hormonal imbalances and related conditions in animals. It helps in maintaining proper hormonal levels and ensuring the overall health and well-being of animals.

Purification Methods

Dissolve adrenosterone i n Me2CO, decolorise it with charcoal, filter, add H2O, Me2CO evaporate and the solid is recrystallised from aqueous EtOH. Also recrystallise it from Et2O or Et2O/pentane and dry it at 110o/0.1mm for 2hours. It can be sublimed under high vacuum. [Reichstein Helv Chim Acta 20 953, 979 1937, Mason et al. J Biol Chem 116 267 1936, Beilstein 7 III 4601.]

InChI:InChI=1/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1

Upstream product

• 53-06-5 17,21-dihydroxy-pregn-4-ene-3,11,20-trione 
• 50-23-7 HYDROCORTISONE 
• 53-06-5 Cortisone 
• 51430-83-2 3-chloro-2-butenyl bromide 
• 74030-33-4 (3S,3aS,9aS,9bS)-3-tert-Butoxy-3a,6-dimethyl-2,3,3a,4,8,9,9a,9b-octahydro-1H-cyclopenta[a]naphthalene-5,7-dione 
• 382-44-5 (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 67-64-1 acetone 
• 1120-73-6 2-methyl-2-cyclopenten-1-one 
• 122314-82-3 (1R,2S,3aS,7aR)-1-Isopropenyl-7a-methyl-2,6-bis-trimethylsilanyloxy-2,3,3a,4,7,7a-hexahydro-1H-indene 
• 104621-25-2 3-((1S,2R,3aS,4R,7aS)-2-Hydroxy-1-isopropenyl-7a-methyl-6-oxo-octahydro-inden-4-yl)-propionic acid isopropyl ester 
• 1882-86-6 11-Keto-16-dehydroprogesterone 

Downstream Products

• 1429-06-7 5β-Androstan-3,11,17-trion 
• 1429-06-7 5α-androstane-3,11,17-trione 
• 1816-85-9 11β-hydroxytestosterone 
• 10123-72-5 3-hydroxy-9,10-seco-androsta-1,3,5⁽¹⁰⁾-triene-11,17-dione 
• 564-35-2 11-ketotestosterone 
• 103042-34-8 3-benzylsulfanyl-androsta-3,5-diene-11,17-dione 
• 122651-08-5 3,3-bis-benzylsulfanyl-androst-4-ene-11,17-dione 
• 1429-06-7 5β-androstane-3,11,17-trione 
• 3924-22-9 (3S,10R,11S,13S,14S,17R)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,11,17-triol 
• 17520-02-4 3β-Hydroxy-androsten-(5)-dion-(11,17) 
• 32693-29-1 3β,16β-Dihydroxy-5α-androstan-11-on 
• 1755-32-4 5αH-androstan-11-one 
• 174505-03-4 (4a’R, 5a’S,6a’S,6b’S,9a’R,11a’R,11b’R)-11‘-(4-methoxyphenyl)-9a’,11b’-dimethyl-1’,5a’,6’,6a’,6b’,7’,8’,9a’,11a',11b’-decahydro-2’H,4’H-dispiro[[1,3]dioxolane-2,3‘-cyclopenta[1,2]phenanthro[8a,9-b]oxirene-9’,2”-[1,3]dioxolane] 
• 174505-02-3 (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane] 

Relevant academic research and scientific papers

Tetrapropylammonium perruthenate as a mild and efficient oxidant for sensitive steroidal alcohols

Tetrapropylammonium perruthenate N-methylmorpholine N-oxide oxidation of steroidal alcohols is described. The reagent combination is mild and gave good yields of the corresponding ketones. Although the oxidation can generate ketones from 3-, 11-, 15-, 17-, and 20-hydroxy steroids, the oxidation of homoallylic alcohols proceeds in low yields. Finally, we observed that the oxidation reagents will convert 17α-hydroxy-2-keto steroids to 17-keto systems in excellent yields.

Side chain removal from corticosteroids by unspecific peroxygenase

Two unspecific peroxygenases (UPO, EC 1.11.2.1) from the basidiomycetous fungi Marasmius rotula and Marasmius wettsteinii oxidized steroids with hydroxyacetyl and hydroxyl functionalities at C17 - such as cortisone, Reichstein's substance S and prednisone

A straightforward chemical synthesis of 17-ketosteroids by cleavage of the C-17-dihydroxy acetone side chain in corticosteroids

A facile and convenient approach to 17-ketosteroids is described. Treatment of steroids containing the C-17-dihydroxy acetone side chain with an excess of sodium methoxide in dry 1,4-dioxane under reflux, affords high yields of the corresponding 17-ketosteroids that are recovered as pure products, without the need of further purification.

Electrochemically Enabled One-Pot Multistep Synthesis of C19 Androgen Steroids

The synthesis of many valuable C19 androgens can be accomplished by removal of the C17 side chain from more abundant corticosteroids, followed by further derivatization of the resulting 17-keto derivative. Conventional chemical reagents pose significant drawbacks for this synthetic strategy, as large amounts of waste are generated, and quenching of the reaction mixture and purification of the 17-ketosteroid intermediate are typically required. Herein, we present mild, safe, and sustainable electrochemical strategies for the preparation of C19 steroids. A reagent and catalyst free protocol for the removal of the C17 side chain of corticosteroids via anodic oxidation has been developed, enabling several one-pot, multistep procedures for the synthesis of androgen steroids. In addition, simultaneous anodic C17 side chain cleavage and cathodic catalytic hydrogenation of a steroid has been demonstrated, rendering a convenient and highly atom economic procedure for the synthesis of saturated androgens.

A simple two-step method for the conversion of [3H]cortisol to [3H]- 11-ketotestosterone

Despite the existence of several protocols, problems appear to persist in the small scale chemical synthesis of radiolabeled 11-ketotestosterone from cortisol. We investigated the possibilities of using the mild oxidant pyridinium dichromate for the oxidative cleavage of the dihydroxyacetone side chain of cortisol and 17β-hydroxysteroid dehydrogenase for the subsequent reduction of the resulting 17-keto group. Our protocol has resulted in consistently high yields of both the intermediate, adrenosterone (70-80%), and the product, 11-ketotestosterone (up to 60%). This, taken together with the convenience and relatively low cost of our method, recommends the protocol for its use for the synthesis of [3H]-11-ketotestosterone for endocrine studies.

Iodine-promoted cleavage of the C-17-dihydroxyacetone side chain of corticosteroids in aqueous ammonia water

A convenient approach to 17-ketosteroids by the iodine-promoted cleavage of the C-17-dihydroxy acetone side chain of corticosteroids is described. Treatment of steroids containing the C-17-dihydroxyacetone side chain with iodine and an excess of aqueous ammonia in acetonitrile at 50°ffords high yields of the corresponding 17-ketosteroids.

Biotransformation of dehydro-epi-androsterone by Aspergillus parasiticus: Metabolic evidences of BVMO activity

The research on the synthesis of steroids and its derivatives is of high interest due to their clinical applications. A particular focus is given to molecules bearing a D-ring lactone like testolactone because of its bioactivity. The Aspergillus genus has been used to perform steroid biotransformations since it offers a toolbox of redox enzymes. In this work, the use of growing cells of Aspergillus parasiticus to study the bioconversion of dehydro-epi-androsterone (DHEA) is described, emphasizing the metabolic steps leading to D-ring lactonization products. It was observed that A. parasiticus is not only capable of transforming bicyclo[3.2.0]hept-2-en-6-one, the standard Baeyer-Villiger monooxygenase (BVMO) substrate, but also yielded testololactone and the homo-lactone 3β-hydroxy-17a-oxa-d-homoandrost-5-en-17-one from DHEA. Moreover, the biocatalyst degraded the lateral chain of cortisone by an oxidative route suggesting the action of a BVMO, thus providing enough metabolic evidences denoting the presence of BVMO activity in A. parasiticus. Furthermore, since excellent biotransformation rates were observed, A. parasiticus is a promising candidate for the production of bioactive lactone-based compounds of steroidal origin in larger scales.

HYDROXYSTEROID COMPOUNDS, THEIR INTERMEDIATES, PROCESS OF PREPARATION, COMPOSITION AND USES THEREOF

The present invention relates to novel steroidal compounds of formula (I), process for preparation of the same and composition comprising these compounds.

Development of a concise synthesis of ouabagenin and hydroxylated corticosteroid analogues

The natural product ouabagenin is a complex cardiotonic steroid with a highly oxygenated skeleton. This full account describes the development of a concise synthesis of ouabagenin, including the evolution of synthetic strategy to access hydroxylation at the C19 position of a steroid skeleton. In addition, approaches to install the requisite butenolide moiety at the C17 position are discussed. Lastly, methodology developed in this synthesis has been applied in the generation of novel analogues of corticosteroid drugs bearing a hydroxyl group at the C19 position.(Chemical Equation Presented).

Identification of new substrates for the CYP106A1-mediated 11-oxidation and investigation of the reaction mechanism

Abstract CYP106A1 from Bacillus megaterium DSM319 was recently shown to catalyze steroid and terpene hydroxylations. Besides producing hydroxylated steroid metabolites at positions 6β, 7β, 9α and 15β, the enzyme displayed previously unknown 11-oxidase activity towards 11β-hydroxysteroids. Novel examples for 11-oxidation were identified and confirmed by 1H and 13C NMR for prednisolone, dexamethasone and 11β-hydroxyandrostenedione. However, only 11β-hydroxyandrostenedione formed a single 11-keto product. The latter reaction was chosen to investigate the kinetic solvent isotope effect on the steady-state turnover of the CYP106A1-mediated 11-oxidation. Our results reveal a large inverse kinetic isotope effect (～0.44) suggesting the involvement of the ferric peroxoanion as a reactive intermediate.