7738-93-4

Usage

Uses

Used in Pharmaceutical Industry:
1-DEHYDROANDRENOSTERONE is used as a pharmaceutical compound for its potential inhibitory effects on estrogen biosynthesis in human placental microsomes. This property makes it a candidate for the development of drugs targeting hormonal imbalances and related conditions.
Used in Sports and Fitness Industry:
1-DEHYDROANDRENOSTERONE is used as a performance-enhancing substance due to its potential androgenic anabolic activity. Athletes and bodybuilders may use it to improve muscle mass, strength, and overall physical performance.
Used in Research and Development:
1-DEHYDROANDRENOSTERONE is used as a research compound for studying its effects on estrogen biosynthesis and its potential applications in the development of new drugs and therapies. Researchers are interested in exploring its antiuterotropic activity and other potential benefits for various medical conditions.

InChI:InChI=1/C19H22O3/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/h7-9,13-14,17H,3-6,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1

Upstream product

• 898-84-0 (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione 
• 53-03-2 Prednison 
• 53-06-5 Cortisone 
• 2899-94-7 17α,20S,21-trihydroxypregna-1,4-diene-3,11-dione 
• 1429-06-7 5β-androstane-3,11,17-trione 
• 50-24-8 prednisolon 
• 382-45-6 adrenosterone 

Downstream Products

• 10123-72-5 3-hydroxy-9,10-seco-androsta-1,3,5⁽¹⁰⁾-triene-11,17-dione 
• 95826-23-6 C₂₂H₂₈O₄ 
• 55675-00-8 1-Methyl-11-oxo-oestron 
• 13952-05-1 11β-hydroxy-17α-ethynyl-17β-hydroxy-1,4-androstadiene-3-one 
• 95826-32-7 Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester 
• 95826-31-6 Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-3H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester 
• 95826-34-9 C₂₉H₃₆O₃S₂ 
• 95826-33-8 Benzoic acid (3aS,5aR,6aS,9aS,9bS,11bR,11cS)-6a,11b-dimethyl-2-oxo-3a,4,5a,6,6a,7,8,9,9a,9b,10,11,11b,11c-tetradecahydro-2H,3H-5-oxa-cyclopenta[a]pyren-7-yl ester 
• 95826-30-5 Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-6a,11b-dimethyl-2-oxo-hexadecahydro-5-oxa-cyclopenta[a]pyren-7-yl ester 
• 73024-23-4 17α-<(2,4-dichlorobenzyl)sulfinyl>-17α-chloro-1,4-androstadiene-3,11-dione 
• 73024-26-7 17β-<(2-methylbenzyl)sulfinyl>-17α-chloro-1,4-androstadiene-3,11-dione 
• 73024-19-8 17β(R)-<(β-phenylethyl)sulfinyl>-17α-chloro-1,4-androstadiene-3,11-dione 
• 83220-39-7 (8S,9S,10R,13S,14S,17R)-17-(Chloro-phenyl-methanesulfinyl)-10,13-dimethyl-7,8,9,10,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,11-dione 
• 73024-13-2 17α-<(2,4-dichlorobenzyl)thio>-1,4-androstadiene-3,11-dione 

Relevant academic research and scientific papers

Bacterial CYP154C8 catalyzes carbon-carbon bond cleavage in steroids

Here, we report the first bacterial cytochrome P450, CYP154C8, that catalyzes the C–C bond cleavage reaction of steroids. A major change in product distribution is observed with CYP154C8, when the reactions are supported by NADPH and spinach redox partners ferredoxin and ferredoxin reductase, compared with previously reported reactions supported by NADH and redox partners containing putidaredoxin and putidaredoxin reductase. The NMR-based structural elucidation of reaction products reveals 21-hydroxyprednisone as the major product for prednisone, while the other product is identified as 1-dehydroadrenosterone obtained due to C–C bond cleavage. A similar pattern of product formation is observed with cortisone, hydrocortisone, and prednisone. The reaction catalyzed by CYP154C8 in the presence of oxygen surrogates also prominently shows the formation of C–C bond cleavage products.

Synthesis of (+)-Cortistatin A

Cortistatin A is a marine steroid with highly selective and perhaps mechanistically unique antiangiogenic activity. Herein we report a synthesis of this natural product by way of cortistatinone , an intermediate ideally suited for investigating the key pharmacophore of the cortistatin family. The synthesis begins with a terrestrial steroid and traverses a route to cortistatin A through the discovery of unique chemical reactivity. Specifically, we demonstrate the first example of a directed, geminal C-H bisoxidation, a new fragmentation cascade to access expanded B-ring steroid systems, a chemoselective cyclization to install the hallmark oxabicycle of the cortistatin family, and a remarkably selective hydrogenation reaction, which should find extensive use in future syntheses of the cortistatins and designed analogues. The synthesis displays a level of brevity, efficiency, and practicality that will be crucial in evaluating the medicinal potential of this fascinating class of marine steroids. Copyright

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.

Scalable synthesis of cortistatin A and related structures

Full details are provided for an improved synthesis of cortistatin A and related structures as well as the underlying logic and evolution of strategy. The highly functionalized cortistatin A-ring embedded with a key heteroadamantane was synthesized by a simple and scalable five-step sequence. A chemoselective, tandem geminal dihalogenation of an unactivated methyl group, a reductive fragmentation/trapping/elimination of a bromocyclopropane, and a facile chemoselective etherification reaction afforded the cortistatin A core, dubbed "cortistatinone". A selective δ16-alkene reduction with Raney Ni provided cortistatin A. With this scalable and practical route, copious quantities of cortistatinone, δ16-cortistatin A (the equipotent direct precursor to cortistatin A), and its related analogues were prepared for further biological studies.

Steroid transformations with Exophiala jeanselmei var. lecanii-corni and Ceratocystis paradoxa

The fungi Exophiala jeanselmei var. lecanii-corni [IMI (International Mycological Institute) 312989, UAMH (University of Alberta Microfungus Collection and Herbarium) 8783] and Ceratocystis paradoxa (IMI 374529, UAMH 8784) have been examined for their potential in steroid biotransformation. The study has determined that E. jeanselmei var. lecanii-corni effected overall anti-Markovnikov hydration on dehydroisoandrosterone, and side-chain degradation on a variety of pregnanes. Both ascomycetes were found to carry out redox reactions of alcohols and ketones as well as 1,4 reduction of α,β-unsaturated carbonyl systems.

Steroid transformations with Fusarium oxysporum var. cubense and Colletotrichum musae

The utility of two locally isolated fungi, pathogenic to banana, for steroid biotransformation has been studied. The deuteromycetes Fusarium oxysporum var. cubense (IMI 326069, UAMH 9013) and Colletotrichum musae (IMI 374528, UAMH 8929) had not been examined previously for this potential. In general, F. oxysporum var. cubense effected 7α hydroxylation on 3β-hydroxy- Δ5-steroids, 6β, 12β, and 15α hydroxylation on steroidal-4-ene-3-ones, side-chain degradation on 17α,21-dihydroxypregnene-3,20-diones, and 15α hydroxylation on estrone. Both strains were shown to perform redox reactions on alcohols and ketones.

Radiolytic degradation scheme for 60Co-irradiated corticosteroids

The cobalt 60 radiolytic degradation products have been identified in the following corticosteroids: cortisone, cortisone acetate, hydrocortisone, hydrocortisone acetate, hydrocortisone sodium succinate, isoflupredone acetate, methylprednisolone, methylprednisolone acetate, prednisolone, prednisolone acetate, and prednisone. Two major types of degradation processes have been identified: loss of the corticoid side chain the D-ring to produce the C-17 ketone and conversion of the C-11 alcohol, if present, to the C-11 ketone. Minor degradation products derived from other changes affecting the side chain are also identified in several corticosteroids. These compounds are frequently associated in corticosteroids as process impurities or degradation compounds. No new radiolytic compounds unique to 60Co-irradiation have been found. The majority of corticosteroids have been shown to be stable to 60Co-irradiation. The rates of radiolytic degradation ranged from 0.2 to 1.4%/Mrad.