Methylprednisolone acetate

Base Information

• Chemical Name: Methylprednisolone acetate
• CAS No.: 53-36-1
• Molecular Formula: C24H32O6
• Molecular Weight: 416.514
• Hs Code.: 32041200
• European Community (EC) Number: 200-171-3
• NSC Number: 48985
• UNII: 43502P7F0P
• DSSTox Substance ID: DTXSID7023302
• Nikkaji Number: J4.144K
• Wikipedia: Methylprednisolone_acetate
• Wikidata: Q27107351
• NCI Thesaurus Code: C48003
• RXCUI: 155323
• Pharos Ligand ID: Z1B6S7RVHF2L
• Metabolomics Workbench ID: 53293
• ChEMBL ID: CHEMBL1364144
• Mol file: 53-36-1.mol

Synonyms:Acetyl Methylprednisolone;acetyl-methylprednisolone;Depo Medrol;Depo Medrone;Depo-Medrol;Depo-Medrone;Methylprednisolone 21 acetate;methylprednisolone acetate;methylprednisolone acetate, (11beta,16alpha)-isomer;methylprednisolone acetate, (11beta,16beta)-isomer;methylprednisolone-21-acetate

Chemical Property of Methylprednisolone acetate

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 5.41E-16mmHg at 25°C
• Melting Point: 206oC
• Refractive Index: 1.58
• Boiling Point: 582.5 °C at 760 mmHg
• PKA: 12.41±0.70(Predicted)
• Flash Point: 196.5 °C
• PSA: 100.90000
• Density: 1.26 g/cm³
• LogP: 2.37440
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, sparingly soluble in acetone and in ethanol (96 per cent).
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 416.21988874
• Heavy Atom Count: 30
• Complexity: 858

Purity/Quality:

99% ^*data from raw suppliers

6α-MethylPrednisolone21-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63-62
• Safety Statements: 36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)COC(=O)C)O
• Isomeric SMILES: C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)C=C4)C)O)C)(C(=O)COC(=O)C)O
• Recent ClinicalTrials: Injection Versus Splinting in Carpal Tunnel Syndrome
• Recent EU Clinical Trials: Knee osteoarthritis Injection Therapy (KNiT) trial
• Uses: Methylprednisolone acetate is used as a glucocorticoid. 6α-Methyl Prednisolone 21-Acetate is used as a glucocorticoid.

Technology Process of Methylprednisolone acetate

There total 26 articles about Methylprednisolone acetate 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:

11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6) + acetic acid (64-19-7,77671-22-8) → methylprednisolone acetate (53-36-1,1048031-82-8)

Guidance literature:

11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione; With iodine; calcium oxide; In methanol; dichloromethane;

acetic acid; With potassium acetate; In acetone; at 45 - 50 ℃; for 2h;

Reference yield:

21-acetoxy-11β-hydroxy-6α-methyl-pregna-1,4,17(20)c-trien-3-one (1968-76-9) → methylprednisolone acetate (53-36-1,1048031-82-8)

Guidance literature:

With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; tert-butyl alcohol; Reagens 4: Pyridin;

DOI:10.1021/ja01604a078

Reference yield:

17,21-dihydroxy-pregn-4-ene-3,11,20-trione (53-06-5,10007-36-0,15779-07-4,35446-72-1,104713-00-0) → methylprednisolone acetate (53-36-1,1048031-82-8)

Guidance literature:

Multi-step reaction with 10 steps

1: aqueous hydrochloric acid; chloroform

2: benzene; toluene-4-sulfonic acid

3: peroxybenzoic acid; benzene / Behandeln unter Ausschluss von Licht, Behandeln des Reaktionsprodukts mit Ameisensaeure und Erwaermen des danach isolierten Reaktionsprodukts mit wss.-methanol. Kalilauge

4: toluene-4-sulfonic acid

5: benzene; diethyl ether

6: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol

7: acetone; toluene-4-sulfonic acid

8: acetic acid; tert-butyl alcohol; selenium dioxide

9: aqueous formic acid

10: pyridine

With pyridine; hydrogenchloride; formic acid; selenium(IV) oxide; thionyl chloride; Perbenzoic acid; diethyl ether; chloroform; toluene-4-sulfonic acid; acetic acid; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/ja01514a055

upstream raw materials:

21-acetoxy-11β-hydroxy-6α-methyl-pregna-1,4,17(20)c-trien-3-one

Methylprednisolone

acetic anhydride

17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione

Downstream raw materials:

17α,21-dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione

21-acetoxy-9-bromo-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione

21-acetoxy-9-fluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione

9,21-difluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione

Refernces

• 1、 -. "9α-dehalogenation process". . . Retrieved 2008/06/13.
• 2、 Anderson,Conradi,Lambert. "Carboxyl group catalysis of acyl transfer reactions in corticosteroid 17- and 21-monoesters". . p. 604 - 610. Retrieved 2007/10/02.