7738-93-4

Basic information

• Product Name: 1-DEHYDROANDRENOSTERONE
• Synonyms: DELTA-1-ADRENOSTERONE;DELTA1-ANDRENOSTERONE;ANDROSTA-1,4-DIENE-3,11,1,7-TRIONE;1-DEHYDROANDRENOSTERONE;1,4-ANDROSTADIENE-3,11,17-TRIONE;1,4-ANDROSTADIEN-3,11,17-TRIONE;1(2)-DEHYDROADRENOSTERONE;D1-Adrenosterone
• CAS NO: 7738-93-4
• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.38
• EINECS: 231-799-6
• Mol File: 7738-93-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 193-195 °C
• Boiling Point: 481.5°Cat760mmHg
• Flash Point: 208.8°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 1.97E-09mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Acetone (Sparingly), Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 1-DEHYDROANDRENOSTERONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-DEHYDROANDRENOSTERONE(7738-93-4)
• EPA Substance Registry System: 1-DEHYDROANDRENOSTERONE(7738-93-4)

Safety Data

• Hazardous Substances Data: 7738-93-4(Hazardous Substances Data)

Usage

Uses

Δ1-Adrenosterone is a derivative of Adrenosterone (A305600), and is suspected to have some inhibitory effects on estrogen biosynthesis in human placental microsomes. Δ1-Adrenosterone also has potential androgenic anabolic and antiuterotropic activity.

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

• 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 
• 53-03-2 Prednison 
• 382-45-6 adrenosterone 
• 53-06-5 Cortisone 
• 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 

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 articles and documents

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.

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.

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.