7|A-Spironolactone

Base Information

• Chemical Name: 7|A-Spironolactone
• CAS No.: 33784-05-3
• Molecular Formula: C24H32O4S
• Molecular Weight: 416.582
• UNII: 8NK6P5VN96
• DSSTox Substance ID: DTXSID10467802
• Nikkaji Number: J1.584.399C
• Wikidata: Q82294876
• Mol file: 33784-05-3.mol

Synonyms:33784-05-3;7|A-Spironolactone;7-Beta-Spironolactone;SC 11940;7beta-Spironolactone;8NK6P5VN96;S-[(7S,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate;7b-Spironolactone;3'-(3-Oxo-7beta-acetylthio-17beta-hydroxyandrost-4-en-17alpha-yl)-propionic acid lactone;UNII-8NK6P5VN96;7.BETA.-SPIRONOLACTONE;Spironolactone impurity E [EP];SCHEMBL18218178;DTXSID10467802;AKOS032958229;3'-(3-Oxo-7|A-acetylthio-17|A-hydroxyandrost-4-en-17|A-yl)-propionic Acid Lactone;SPIRONOLACTONE IMPURITY E [EP IMPURITY];A899619;7beta-(Acetylthio)-17alpha-hydroxy-3-oxopregn-4-ene-21-carboxylic acid gamma-lactone;17.ALPHA.-PREGN-4-ENE-21-CARBOXYLIC ACID, 17-HYDROXY-7.BETA.-MERCAPTO-3-OXO-, .GAMMA.-LACTONE, ACETATE;17alpha-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7beta-mercapto-3-oxo-, gamma-lactone, acetate;3'-(3-OXO-7.BETA.-ACETYLTHIO-17.BETA.-HYDROXYANDROST-4-EN-17.ALPHA.-YL)-PROPIONIC ACID LACTONE;7.BETA.-(ACETYLTHIO)-17.ALPHA.-HYDROXY-3-OXOPREGN-4-ENE-21-CARBOXYLIC ACID .GAMMA.-LACTONE;PREGN-4-ENE-21-CARBOXYLIC ACID, 7-(ACETYLTHIO)-17-HYDROXY-3-OXO-, .GAMMA.-LACTONE, (7.BETA.,17.ALPHA.)-;Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7beta,17alpha)-;S-((2R)-3,5-DIOXO-3,4-DIHYDRO-5H-SPIRO(ANDROST-4-ENE-17,2-FURAN)-7.BETA.-YL) ETHANETHIOATE;S-((2R)-3,5-Dioxo-3,4-dihydro-5H-spiro(androst-4-ene-17,2-furan)-7beta-yl) ethanethioate

Chemical Property of 7|A-Spironolactone

Chemical Property:

• Melting Point: 227-230 °C
• Boiling Point: 597.0±50.0 °C(Predicted)
• PSA: 85.74000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 4.85230
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 416.20213067
• Heavy Atom Count: 29
• Complexity: 818

Purity/Quality:

99%, ^*data from raw suppliers

7β-Spironolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)SC1CC2=CC(=O)CCC2(C3C1C4CCC5(C4(CC3)C)CCC(=O)O5)C
• Isomeric SMILES: CC(=O)S[C@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCC(=O)O5)C
• Uses: 7β-Spironolactone is the 7β-isomer of Spironolactone (S683000). It binds effectively to human plasma proteins. 7β-Spironolactone (Spironolactone EP Impurity E) is the 7β-isomer of Spironolactone (S683000). It binds effectively to human plasma proteins.

Technology Process of 7|A-Spironolactone

There total 3 articles about 7|A-Spironolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

canrenone (976-71-6) + tiolacetic acid (507-09-5) → β-spironolactone (33784-05-3) + SPIRONOLACTONE (52-01-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; for 1h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00282a041

Reference yield:

→ 3-<3-Oxo-7α-acetylthio-17β-hydroxy-4-androsten-17α-yl>-propionsaeure-lacton (52-01-7,33784-05-3,81769-08-6)

Guidance literature:

3-<3-Oxo-17β-hydroxy-4.6-androstadien-17α-yl>-propionsaeure-lacton, Thioessig- saeure, Δ, neben geringen Mengen an 3-<3-Oxo-7β-acetylthio-17β-hydroxy-4-androsten-17α-yl>-propionsaeure-lacton;

DOI:10.1021/jo01056a515

Reference yield:

→ 3-<3-Oxo-7β-acetylthio-17β-hydroxy-4-androsten-17α-yl>-propionsaeure-lacton (52-01-7,33784-05-3,81769-08-6)

Guidance literature:

3-<3-Oxo-17β-hydroxy-4.6-androstadien-17α-yl>-propionsaeure-lacton, Thioessig- saeure, Δ, in geringen Mengen neben 3-<3-Oxo-7α-acetylthio-17β-hydroxy-4-androsten-17α-yl>-propionsaeure-lacton;

DOI:10.1021/jo01056a515

upstream raw materials:

canrenone

tiolacetic acid

Refernces

• 1、 Wuts, Peter G. M.,Ritter, Allen R.. "A Novel Synthesis of Spironolactone. An Application of the Hydroformylation Reaction". . p. 5180 - 5182. Retrieved 1989.