Acetoxanon

Base Information

• Chemical Name: Acetoxanon
• CAS No.: 566-78-9
• Molecular Formula: C23H34 O4
• Molecular Weight: 374.521
• European Community (EC) Number: 209-298-9
• NSC Number: 66372
• UNII: DX3XOD2S6B
• DSSTox Substance ID: DTXSID60878641
• Nikkaji Number: J6.520J
• Wikipedia: Prebediolone_acetate
• Wikidata: Q27276654
• NCI Thesaurus Code: C98246
• ChEMBL ID: CHEMBL1328310
• Mol file: 566-78-9.mol

Synonyms:Acetoxanon;21-ACETOXYPREGNENOLONE;Artisone acetate;566-78-9;Prebediolone acetate;Artisone;Pregnenolone 21-acetate;A.O.P.;Artixone acetate;UNII-DX3XOD2S6B;NSC 66372;DX3XOD2S6B;MLS000069530;MLS001146901;EINECS 209-298-9;NSC-66372;[2-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;SMR000058628;21-Acetoxy-3beta-hydroxypregn-5-en-20-one;3beta-Hydroxy-21-acetoxypregn-5-en-20-one;21-Acetoxy-3.beta.-hydroxypregn-5-en-20-one;3.beta.-Hydroxy-21-acetoxypregn-5-en-20-one;3-beta,21-Dihydroxypregn-5-en-20-one 21-acetate;(3.beta.)-21-(Acetyloxy)-3-hydroxypregn-5-en-20-one;Pregn-5-en-20-one, 3.beta.,21-dihydroxy-, 21-acetate;Pregn-5-en-20-one, 21-(acetyloxy)-3-hydroxy-, (3.beta.)-;ACETOXAN;Opera_ID_17;(3-beta)-21-(Acetyloxy)-3-hydroxypregn-5-en-20-one;SCHEMBL34011;CHEMBL1328310;DTXSID60878641;CHEBI:135579;HMS2236D06;NSC66372;21-ACETOXYPREGNENOLONE [MI];3-Hydroxy-20-oxopregn-5-en-21-yl acetate #;5-Pregnene-3beta,21-diol-20-one 21-acetate;Pregn-5-en-20-one,21-dihydroxy-, 21-acetate;3beta,21-Dihydroxy-5-pregnen-20-one 21-acetate;5-Pregnene-3.beta.,21-diol-20-one 21-acetate;SR-01000000026;SR-01000000026-3;Q27276654;Pregn-5-en-20-one, 3beta,21-dihydroxy-, 21-acetate;Pregn-5-en-20-one, 21-(acetyloxy)-3-hydroxy-, (3beta)-

Chemical Property of Acetoxanon

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 500.2°Cat760mmHg
• Flash Point: 166.6°C
• PSA: 63.60000
• Density: 1.15g/cm³
• LogP: 4.05850
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 374.24570956
• Heavy Atom Count: 27
• Complexity: 667

Purity/Quality:

98%min ^*data from raw suppliers

21-ACETOXYPREGNENOLONE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: CC(=O)OCC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• Uses: antiarthritic, precursor in corticoid biosynthesis

Technology Process of Acetoxanon

There total 21 articles about Acetoxanon 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:

3β-[tert-butyl(dimethyl)silyl]oxy-20-oxopregn-5-en-21-yl acetate → 21-acetoxypregnenolone (566-78-9)

Guidance literature:

With pyridine hydrogenfluoride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1039/d1ob01178b

Reference yield:

21-acetoxy-3β-formyloxy-pregn-5-en-20-one (115098-53-8) → 21-acetoxypregnenolone (566-78-9)

Guidance literature:

With aluminum oxide;

DOI:10.1021/ja01575a055

Reference yield:

3β-hydroxypregn-5-ene-16,20-dione (911442-53-0) → 21-acetoxypregnenolone (566-78-9)

Guidance literature:

Multi-step reaction with 6 steps

2: toluene-4-sulfonic acid

5: palladium/charcoal; ethyl acetate / Hydrogenation

6: Al₂O₃

With aluminum oxide; palladium on activated charcoal; toluene-4-sulfonic acid; ethyl acetate;

DOI:10.1021/ja01575a055

upstream raw materials:

Pregnenolone

Phenyl glycidyl ether

3β-hydroxy-21-iodo-pregn-5-en-20-one

triethylammonium acetate

Downstream raw materials:

21-hydroxypregn-4,6-diene-3,20-dione 21-acetate

etienic acid

5-pregnen-3β-ol

pregn-5,20-diene-3β-ol

Refernces

• 1、 -. "Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor". . . Retrieved 2008/06/13.