Production Method 1

853-23-6

Reaction Conditions

1.1 Reagents: Sodium nitrite Solvents: Acetic acid

Reference

A simple method for the fission of semicarbazones

Goldschmidt, St.; et al, Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, 1946, 65, 796-8

Production Method 2

853-23-6

Reaction Conditions

1.1 Reagents: Pyridine ,  Phosphorus oxychloride Solvents: Pyridine

Reference

The Beckmann rearrangement of 17-α-hydroxy-20-oxosteroid oximes

Schmidt-Thome, Josef, Justus Liebigs Annalen der Chemie, 1957, 603, 43-5

Production Method 3

53-43-0

853-23-6

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase ;  72 h, 30 °C

Reference

Lipase-catalyzed preparation of biologically active esters of dehydroepiandrosterone

Bruttomesso, Andrea C.; et al, Biocatalysis and Biotransformation, 2004, 22(3), 215-220

Production Method 4

54498-67-8

853-23-6

Reaction Conditions

1.1 Reagents: Copper sulfate (silica gel-bound) Solvents: Chloroform

Reference

Cleavage of thioacetals promoted by copper(II) sulfate adsorbed on silica gel

Caballero, Gerardo M.; et al, Journal of Chemical Research, 1989, (10), 320-1

Production Method 5

6585-68-8

853-23-6

Reaction Conditions

1.1 Reagents: Propanedioic acid, 2-diazo-, 1,3-dimethyl ester Catalysts: [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]chlorocopper Solvents: Toluene ;  2 h, reflux; 2 h, reflux
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Regioselective and Stereospecific Copper-Catalyzed Deoxygenation of Epoxides to Alkenes

Yu, Jingxun; et al, Organic Letters, 2016, 18(18), 4734-4737

Production Method 6

122914-94-7

853-23-6

Reaction Conditions

1.1 Reagents: Water Catalysts: Dimethyl sulfoxide ,  Cyanuric chloride Solvents: Acetonitrile ;  rt; 12 h, rt

Reference

From the Studies of Hydration and Hydrolysis Reactions to the Discovery of a New Organocatalyst and Its Further Applications in Acetalization and Glycosylation

Yuan, Wenjiao; et al, Asian Journal of Organic Chemistry, 2017, 6(10), 1428-1439

Production Method 7

481-29-8

853-23-6

Reaction Conditions

1.1 Catalysts: 1,3-Dibromo-5,5-dimethylhydantoin ;  20 h, 70 °C

Reference

1,3-dibromo-5,5-dimethylhydantoin as a precatalyst for activation of carbonyl functionality

Cebular, Klara; et al, Molecules, 2019, 24(14),

Production Method 8

58077-29-5

853-23-6

Reaction Conditions

1.1 Reagents: Water Catalysts: Dimethyl sulfoxide ,  Cyanuric chloride Solvents: Acetonitrile ;  rt; 10 min, rt

Reference

From the Studies of Hydration and Hydrolysis Reactions to the Discovery of a New Organocatalyst and Its Further Applications in Acetalization and Glycosylation

Yuan, Wenjiao; et al, Asian Journal of Organic Chemistry, 2017, 6(10), 1428-1439

Production Method 9

19637-35-5

853-23-6

Reaction Conditions

1.1 Reagents: Acetyl chloride

Reference

Direct, high-yield transformation of tetrahydropyranyl ethers to acetates

Bakos, Tamas; et al, Synthetic Communications, 1989, 19(3-4), 523-8

Production Method 10

17916-30-2

853-23-6

Reaction Conditions

1.1 Reagents: Diphenyl disulfide ,  Tributylphosphine Solvents: Pyridine
1.2 Reagents: Acetic anhydride

Reference

Reduction of oximes and aliphatic nitro compounds to imines for further in situ reactions: a novel synthesis of pyrroles and pyrrolin-2-ones

Barton, Derek H. R.; et al, Journal of the Chemical Society, 1986, (12), 2243-52

Production Method 11

17916-30-2

853-23-6

Reaction Conditions

1.1 Reagents: Pyridine ,  Hydrochloric acid ,  Phosphorus oxychloride Solvents: Water ;  1 h, 0 °C

Reference

Synthesis and Characterization of 3β-Substituted Amides of 17a-Aza-D-homo- 4-androsten-17-one as Potent 5α-Reductase Inhibitors and Antimicrobial Agents

Malhotra, Manav; et al, Current Topics in Medicinal Chemistry (Sharjah, 2013, 13(16), 2047-2061

Production Method 12

17921-59-4

853-23-6

Reaction Conditions

1.1 Reagents: Silica ,  Copper sulfate Solvents: Chloroform

Reference

Cleavage of acetals promoted by copper(II) sulfate adsorbed on silica gel

Caballero, Gerardo M.; et al, Synthetic Communications, 1995, 25(3), 395-404

Production Method 13

2174-13-2

853-23-6

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Acetone ,  Toluene ,  Water ;  1 h, 0 - 30 °C; 4 h, 20 - 30 °C; 0 - 5 °C; 2 h, 0 - 5 °C

Reference

Synthesis process study of 5-androstene-3β-ol-17-one-3-acetate

Shi, Cheng; et al, Shandong Huagong, 2012, 41(1), 17-19

Production Method 14

1061-54-7

853-23-6

Reaction Conditions

Reference

Efficient synthesis of 7-keto-DHEA acetate

Liu, Chun; et al, Yunnan Daxue Xuebao, 2007, 29(5), 504-506

Production Method 15

53-43-0

853-23-6

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide ,  4-(Dimethylamino)pyridine

Reference

Novel dehydroepiandrosterone benzimidazolyl derivatives as 5α-reductase isozymes inhibitors

Arellano, Yazmin; et al, Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, 31(6), 908-914

Production Method 16

571-36-8

853-23-6

Reaction Conditions

1.1 Reagents: Glucose ,  NAD ,  Sodium carbonate ,  Monopotassium phosphate Catalysts: Glucose dehydrogenase ,  Carbonyl reductase Solvents: Ethyl acetate ,  Water ;  4 h, pH 6.3 - 6.5, 32.5 °C; 8 h, 32.5 °C; 22 h, 32.5 °C
1.2 Reagents: Sodium acetate Solvents: Acetic acid ;  16 h, 60 °C; 60 °C → 25 °C
1.3 Reagents: Methanol Solvents: Water ;  10 min, 25 °C; 1 h, 25 °C

Reference

Development of a Chemoenzymatic Process for Dehydroepiandrosterone Acetate Synthesis

Fryszkowska, Anna; et al, Organic Process Research & Development, 2016, 20(8), 1520-1528

dehydroisoandrosterone 3-acetate Raw materials

• Androstan-17-one,3-(acetyloxy)-5,6-epoxy-, (3b,5b,6b)-
• (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-3-(oxan-2-yloxy)-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• Spirost-5-en-3-ol,acetate, (3b,25R)-
• [(3S,10R,13S)-10,13-Dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-3-yl] acetate
• Androst-5-ene-3,17-dione
• Pregnenolone-16-ene Acetate Oxime
• Pregn-5-en-20-one,3-(acetyloxy)-, 20-oxime, (3b)-
• Dehydroepiandrosterone
• 3-O-Acetylandrostenone hydrazone
• (10,13-dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-oxathiolane]-3-yl) Acetate
• Epiandrosterone
• Androsta-5,16-dien-3-ol, 17-methoxy-, 3-acetate, (3β)-

dehydroisoandrosterone 3-acetate Preparation Products

• dehydroisoandrosterone 3-acetate (853-23-6)

• 1. Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies
  Phys. Chem. Chem. Phys., 1999,1, 3561-3565
• 2. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 3. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
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• 4. Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent?
  Yukiya Kitayama Polym. Chem., 2014,5, 2784-2792
• 5. Evolution of dealloying induced strain in nanoporous gold crystals?
  Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693

• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroid esters

Dehydroisoandrosterone 3-acetate (CAS No. 853-23-6): A Comprehensive Overview

Dehydroisoandrosterone 3-acetate, commonly referred to by its CAS number 853-23-6, is a significant compound in the field of endocrinology and pharmacology. This compound, belonging to the class of steroid derivatives, has garnered considerable attention due to its unique biochemical properties and potential therapeutic applications. Understanding its structure, synthesis, biological effects, and recent research advancements provides valuable insights into its role in modern medicine.

The molecular structure of Dehydroisoandrosterone 3-acetate consists of a steroidal backbone with an acetylated hydroxyl group at the 3-position. This modification enhances its stability and bioavailability, making it a more suitable candidate for pharmaceutical formulations. The compound is structurally related to natural androgens, which explains its influence on various physiological processes. Its chemical formula, C??H??O?, reflects its complex composition and the presence of multiple functional groups that contribute to its biological activity.

In terms of synthesis, Dehydroisoandrosterone 3-acetate is typically derived from natural precursors or synthesized through controlled chemical reactions. The acetylation process at the 3-position is crucial, as it alters the compound's reactivity and interaction with biological targets. Advanced synthetic methodologies have improved the yield and purity of this compound, enabling more efficient production for research and clinical purposes.

The biological effects of Dehydroisoandrosterone 3-acetate are multifaceted, influencing various hormonal pathways and physiological processes. Research has shown that this compound can modulate sex hormone-binding globulin (SHBG) levels, potentially affecting testosterone and estrogen bioavailability. Additionally, it has been investigated for its role in metabolic regulation, suggesting potential benefits in managing conditions such as obesity and diabetes. These findings highlight the compound's therapeutic potential beyond traditional endocrine applications.

Recent studies have explored the pharmacological properties of Dehydroisoandrosterone 3-acetate in relation to inflammation and immune response modulation. Preclinical trials have demonstrated its ability to reduce inflammatory markers in animal models, indicating a possible role in treating chronic inflammatory diseases. Furthermore, its interaction with nuclear receptors has been studied for potential applications in oncology, where it may influence tumor growth and progression.

The compound's potential applications extend to neurology, where preliminary research suggests that Dehydroisoandrosterone 3-acetate may have neuroprotective effects. Studies have indicated that it can cross the blood-brain barrier and interact with neurotransmitter systems, potentially offering benefits in neurodegenerative disorders such as Alzheimer's disease. These findings underscore the broad therapeutic scope of this steroid derivative.

In clinical settings, Dehydroisoandrosterone 3-acetate is being evaluated for use in hormone replacement therapy (HRT), particularly for individuals with impaired endocrine function. Its ability to enhance SHBG levels may provide a balanced approach to managing hormonal imbalances without excessive side effects. Clinical trials are ongoing to assess its long-term safety and efficacy in various populations.

The regulatory landscape for Dehydroisoandrosterone 3-acetate is evolving as new research emerges. Regulatory bodies are closely monitoring its use to ensure safety and efficacy standards are met. As more data becomes available, the compound's approval for specific indications may expand, offering new treatment options for patients with unmet medical needs.

Future directions in research focus on optimizing delivery systems for Dehydroisoandrosterone 3-acetate to enhance its therapeutic profile. Nanotechnology-based formulations are being explored to improve bioavailability and targeted delivery, potentially increasing the compound's efficacy while minimizing side effects. Additionally, investigating synergistic combinations with other pharmacological agents may unlock new therapeutic possibilities.

The economic impact of Dehydroisoandrosterone 3-acetate is also noteworthy, as it represents a significant area of investment in pharmaceutical research and development. Companies specializing in steroid derivatives are prioritizing this compound due to its diverse applications and potential market demand. As innovation continues, the economic benefits of this research are likely to translate into advanced treatments accessible to patients worldwide.

In conclusion, Dehydroisoandrosterone 3-acetate (CAS No. 853-23-6) is a versatile compound with broad implications in medicine and biotechnology. Its unique biochemical properties make it a valuable tool for studying hormonal mechanisms and developing new therapies. With ongoing research uncovering new applications and improving synthetic methods, this compound is poised to play an increasingly important role in addressing various health challenges.

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• 1769-67-1(Pregn-5-en-20-one,3-(acetyloxy)-16-methyl-, (3b,16b)-)
• 1863-41-8(Pregn-5-en-20-one,3-(acetyloxy)-16-methyl-, (3b,16a)-)
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