53-36-1

Basic information

• Product Name: Methylprednisolone acetate
• Synonyms: depo-medrone;depo-methylprednisolone;depo-methylprednisoloneacetate;depot-medrol;u8210;urbasoncrystalsuspension;methylprednisolone 21-acetate;METHYLPREDNISOLONE ACETATE
• CAS NO: 53-36-1
• Molecular Formula: C₂₄H₃₂O₆
• Molecular Weight: 416.51
• EINECS: 200-171-3
• Product Categories: Miscellaneous Biochemicals;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Steroid and Hormone;API
• Mol File: 53-36-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 192-195°C
• Boiling Point: 454.82°C (rough estimate)
• Flash Point: 196.5 °C
• Appearance: Off-White Solid
• Density: 1.1156 (rough estimate)
• Vapor Pressure: 5.41E-16mmHg at 25°C
• Refractive Index: 1.4593 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Practically insoluble in water, sparingly soluble in acetone and in ethanol (96 per cent).
• PKA: 12.41±0.70(Predicted)
• CAS DataBase Reference: Methylprednisolone acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methylprednisolone acetate(53-36-1)
• EPA Substance Registry System: Methylprednisolone acetate(53-36-1)

Safety Data

• Hazard Codes: Xn
• Statements: 63-62
• Safety Statements: 36/37-24/25
• Hazardous Substances Data: 53-36-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 53-36-1 differently. You can refer to the following data:
1. Methylprednisolone acetate is used as a glucocorticoid.
2. 6α-Methyl Prednisolone 21-Acetate is used as a glucocorticoid.

Definition

ChEBI: An acetate ester resulting from the formal condensation of the 21-hydroxy function of 6alpha-methylprednisolone compound with acetic acid.

Brand name

Medrol (Pharmacia & Upjohn).

InChI:InChI=1/C24H32O6/c1-13-9-16-17-6-8-24(29,20(28)12-30-14(2)25)23(17,4)11-19(27)21(16)22(3)7-5-15(26)10-18(13)22/h5,7,10,13,16-17,19,21,27,29H,6,8-9,11-12H2,1-4H3

Synthetic route

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

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

Methylprednisolone (83-43-2) + acetic anhydride (108-24-7) → methylprednisolone acetate (53-36-1)

Conditions	Yield
With pyridine

17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (86401-94-7) → Methylprednisolone (83-43-2) + methylprednisolone acetate (53-36-1)

Conditions	Yield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;

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)

Conditions

Yield

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 View Scheme

11β,21-dihydroxy-6α-methyl-pregna-4,17(20)c-dien-3-one (3386-04-7, 14423-17-7) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Dehydrierung durch Septomyxa affinis und anschliessende Acetylierung 2: diacetoxy-phenyl-iodan; OsO4; tert-butyl alcohol / Reagens 4: Pyridin View Scheme

(20Ξ)-11β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-pregna-1,4-dien-3-one (117888-35-4) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous formic acid 2: pyridine View Scheme

(20Ξ)-11β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-pregn-4-en-3-one (123292-91-1) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; tert-butyl alcohol; selenium dioxide 2: aqueous formic acid 3: pyridine View Scheme

17α,20;20,21-bismethylenedioxypregn-4-ene-3,11-dione (3607-68-9) → methylprednisolone acetate (53-36-1)

Conditions

Yield

Multi-step reaction with 9 steps 1: benzene; toluene-4-sulfonic acid 2: peroxybenzoic acid; benzene / Behandeln unter Ausschluss von Licht, Behandeln des Reaktionsprodukts mit Ameisensaeure und Erwaermen des danach isolierten Reaktionsprodukts mit wss.-methanol. Kalilauge 3: toluene-4-sulfonic acid 4: benzene; diethyl ether 5: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol 6: acetone; toluene-4-sulfonic acid 7: acetic acid; tert-butyl alcohol; selenium dioxide 8: aqueous formic acid 9: pyridine View Scheme

(20Ξ)-17,20;20,21-bis-methylenedioxy-5α-pregnane-3,6,11-trione (55701-21-8) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 7 steps 1: toluene-4-sulfonic acid 2: benzene; diethyl ether 3: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol 4: acetone; toluene-4-sulfonic acid 5: acetic acid; tert-butyl alcohol; selenium dioxide 6: aqueous formic acid 7: pyridine View Scheme

(20Ξ)-3,3-ethanediyldioxy-6-methyl-17,20;20,21-bis-methylenedioxy-pregn-5-en-11β-ol → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: acetone; toluene-4-sulfonic acid 2: acetic acid; tert-butyl alcohol; selenium dioxide 3: aqueous formic acid 4: pyridine View Scheme

6-methyl-11-oxo-3-pyrrolidino-pregna-3,5,17(20)c-trien-21-oic acid methyl ester (1968-77-0) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4; diethyl ether / Behandeln des Reaktionsprodukts mit wss.-methanol.Alkalilauge 2: Dehydrierung durch Septomyxa affinis und anschliessende Acetylierung 3: diacetoxy-phenyl-iodan; OsO4; tert-butyl alcohol / Reagens 4: Pyridin View Scheme

(8′S,9′S,10′R,13′S,14′S,17′R)-10′,13′-dimethyl-1′,2′,4′,7′,8′,9′,10′,12′,13′,14′,15′,16′-dodecahydro-11′H-trispiro[[1,3]dioxolane-2,3′-cyclopenta[a]phenanthrene-17′,4''-[1,3]dioxolane-5'',4'''-[1,3]dioxolan]-11′-one (52248-40-5) → methylprednisolone acetate (53-36-1)

Conditions

Yield

Multi-step reaction with 8 steps 1: peroxybenzoic acid; benzene / Behandeln unter Ausschluss von Licht, Behandeln des Reaktionsprodukts mit Ameisensaeure und Erwaermen des danach isolierten Reaktionsprodukts mit wss.-methanol. Kalilauge 2: toluene-4-sulfonic acid 3: benzene; diethyl ether 4: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol 5: acetone; toluene-4-sulfonic acid 6: acetic acid; tert-butyl alcohol; selenium dioxide 7: aqueous formic acid 8: pyridine View Scheme

(20Ξ)-3,3-ethanediyldioxy-6β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-5α-pregnan-11-one (123885-50-7) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol 2: acetone; toluene-4-sulfonic acid 3: acetic acid; tert-butyl alcohol; selenium dioxide 4: aqueous formic acid 5: pyridine View Scheme

(20Ξ)-3,3-ethanediyldioxy-17,20;20,21-bis-methylenedioxy-5α-pregnane-6,11-dione (107157-45-9) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: benzene; diethyl ether 2: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol 3: acetone; toluene-4-sulfonic acid 4: acetic acid; tert-butyl alcohol; selenium dioxide 5: aqueous formic acid 6: pyridine View Scheme

21-acetoxy-9-bromo-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione (93052-90-5) → methylprednisolone acetate (53-36-1)

9α-chloro-11β,17α,21-trihydroxy-6α-methylpregna-1,4-diene-3,20-dione 21-acetate → methylprednisolone acetate (53-36-1)

C26H42O6 → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / tetrahydrofuran / pH 2 - 3 2.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h 3.1: iodine; calcium oxide / methanol; dichloromethane 3.2: 2 h / 45 - 50 °C View Scheme

11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione (7055-53-0) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h 2.1: iodine; calcium oxide / methanol; dichloromethane 2.2: 2 h / 45 - 50 °C View Scheme

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

Conditions	Yield
Stage #1: 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione With iodine; calcium oxide In methanol; dichloromethane Stage #2: acetic acid With potassium acetate In acetone at 45 - 50℃; for 2h;

17-hydroxy-pregn-4-ene-3,11,20-trione (1882-82-2) → methylprednisolone acetate (53-36-1)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: trimethyloxosulfonium bromide; orthoformic acid triethyl ester / 5 h 2.1: sodium tetrahydroborate / tetrahydrofuran / 12 h 3.1: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h 4.1: magnesium / tetrahydrofuran / 4 h 5.1: sulfuric acid / tetrahydrofuran / pH 2 - 3 6.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h 7.1: iodine; calcium oxide / methanol; dichloromethane 7.2: 2 h / 45 - 50 °C View Scheme

3,3;20,20-bis-ethanediyldioxy-17-hydroxy-pregn-5-en-11-one (74332-34-6) → methylprednisolone acetate (53-36-1)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 12 h 2.1: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h 3.1: magnesium / tetrahydrofuran / 4 h 4.1: sulfuric acid / tetrahydrofuran / pH 2 - 3 5.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h 6.1: iodine; calcium oxide / methanol; dichloromethane 6.2: 2 h / 45 - 50 °C View Scheme

3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol (41870-77-3) → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h 2.1: magnesium / tetrahydrofuran / 4 h 3.1: sulfuric acid / tetrahydrofuran / pH 2 - 3 4.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h 5.1: iodine; calcium oxide / methanol; dichloromethane 5.2: 2 h / 45 - 50 °C View Scheme

C25H38O7 → methylprednisolone acetate (53-36-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: magnesium / tetrahydrofuran / 4 h 2.1: sulfuric acid / tetrahydrofuran / pH 2 - 3 3.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h 4.1: iodine; calcium oxide / methanol; dichloromethane 4.2: 2 h / 45 - 50 °C View Scheme

methylprednisolone acetate (53-36-1) → Methylprednisolone (83-43-2)

Conditions	Yield
Hydrolysis;
With potassium hydroxide In methanol; dichloromethane at 10 - 15℃; for 0.333333h; Inert atmosphere;

methylprednisolone acetate (53-36-1) → 2-((6S,10R,13S)-17-hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (93239-37-3)

Conditions	Yield
With pyridine; thionyl chloride
With pyridine; N-bromoacetamide
With sulfur dioxide; methanesulfonyl chloride In tetrahydrofuran; N,N-dimethyl-formamide Cooling with ice;

methylprednisolone acetate (53-36-1) → Methylprednisolone (83-43-2) + 17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (86401-94-7)

Conditions	Yield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;

methylprednisolone acetate (53-36-1) → 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6870-94-6) + 11β-hydroxy-6α-methyl-1,4-androstadiene-3,17-dione (61919-52-6) + 6α-methylprednisone acetate

Conditions	Yield
Product distribution; Rate constant; Irradiation; radiolytic degradation;

methylprednisolone acetate (53-36-1) → 9-fluoro-11β,17,21-trihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione (382-52-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: N-bromo-acetamide; pyridine 2: CH2Cl2; tert-butyl alcohol; aqueous HClO4 3: acetone; potassium acetate 4: CH2Cl2; water; HF 5: aqueous methanol. KHCO3 View Scheme

methylprednisolone acetate (53-36-1) → 9,21-difluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione (359-80-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: N-bromo-acetamide; pyridine 2: CH2Cl2; tert-butyl alcohol; aqueous HClO4 3: acetone; potassium acetate 4: CH2Cl2; water; HF 5: aqueous methanol. KHCO3 6: ueber mehrere Stufen View Scheme

methylprednisolone acetate (53-36-1) → 21-acetoxy-9-fluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione (432-33-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: N-bromo-acetamide; pyridine 2: CH2Cl2; tert-butyl alcohol; aqueous HClO4 3: acetone; potassium acetate 4: CH2Cl2; water; HF View Scheme

methylprednisolone acetate (53-36-1) → 21-acetoxy-9-bromo-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione (93052-90-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-bromo-acetamide; pyridine 2: CH2Cl2; tert-butyl alcohol; aqueous HClO4 View Scheme

methylprednisolone acetate (53-36-1) → 21-acetoxy-9,11β-epoxy-17-hydroxy-6α-methyl-9β-pregna-1,4-diene-3,20-dione (115322-26-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-bromo-acetamide; pyridine 2: CH2Cl2; tert-butyl alcohol; aqueous HClO4 3: acetone; potassium acetate View Scheme

methylprednisolone acetate (53-36-1) → 17α,21-dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione (111264-84-7, 91523-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Hydrolysis 2: N-bromo-acetamide; pyridine View Scheme

methylprednisolone acetate (53-36-1) → 21-acetoxy-17-hydroxy-6α-methyl-11β-trifluoroacetoxy-1,4-pregnadiene-3,20-dione (86413-46-9)

Conditions	Yield
With trifluoroacetic anhydride In pyridine; dichloromethane

methylprednisolone acetate (53-36-1) → 2-oxo-2-((6S,10R,13S)-6,10,13-trimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)ethyl acetate (52212-12-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfur dioxide; methanesulfonyl chloride / N,N-dimethyl-formamide; tetrahydrofuran / Cooling with ice 2: pyridine hydrochloride / toluene / Heating 3: hydrogenchloride; water / tetrahydrofuran 4: potassium carbonate / N,N-dimethyl-formamide / Heating View Scheme
Multi-step reaction with 4 steps 1: sulfur dioxide / N,N-dimethyl-formamide; tetrahydrofuran / Cooling with ice 2: pyridine hydrochloride / toluene / Heating 3: hydrogenchloride / tetrahydrofuran 4: potassium carbonate / N,N-dimethyl-formamide / Heating View Scheme

Upstream product

• 41870-77-3 3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol 
• 74332-34-6 3,3;20,20-bis-ethanediyldioxy-17-hydroxy-pregn-5-en-11-one 
• 1882-82-2 17-hydroxy-pregn-4-ene-3,11,20-trione 
• 6870-94-6 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione 
• 64-19-7 acetic acid 
• 7055-53-0 11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione 
• 93052-90-5 21-acetoxy-9-bromo-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione 
• 107157-45-9 (20Ξ)-3,3-ethanediyldioxy-17,20;20,21-bis-methylenedioxy-5α-pregnane-6,11-dione 
• 123885-50-7 (20Ξ)-3,3-ethanediyldioxy-6β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-5α-pregnan-11-one 
• 52248-40-5 (8′S,9′S,10′R,13′S,14′S,17′R)-10′,13′-dimethyl-1′,2′,4′,7′,8′,9′,10′,12′,13′,14′,15′,16′-dodecahydro-11′H-trispiro[[1,3]dioxolane-2,3′-cyclopenta[a]phenanthrene-17′,4''-[1,3]dioxolane-5'',4'''-[1,3]dioxolan]-11′-one 
• 1968-77-0 6-methyl-11-oxo-3-pyrrolidino-pregna-3,5,17⁽²⁰⁾c-trien-21-oic acid methyl ester 
• 55701-21-8 (20Ξ)-17,20;20,21-bis-methylenedioxy-5α-pregnane-3,6,11-trione 
• 3607-68-9 17α,20;20,21-bismethylenedioxypregn-4-ene-3,11-dione 
• 123292-91-1 (20Ξ)-11β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-pregn-4-en-3-one 

Downstream Products

• 83-43-2 Methylprednisolone 
• 86401-94-7 17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione 
• 6870-94-6 11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione 
• 61919-52-6 11β-hydroxy-6α-methyl-1,4-androstadiene-3,17-dione 
• 111264-84-7 17α,21-dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione 
• 93052-90-5 21-acetoxy-9-bromo-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione 
• 432-33-7 21-acetoxy-9-fluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione 
• 359-80-8 9,21-difluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione 
• 382-52-5 9-fluoro-11β,17,21-trihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione 

Relevant articles and documents

A methylprednisolone production process and production apparatus (by machine translation)

The invention discloses a methylprednisolone production device, including connected according to the procedure of the reaction, shui xifu, centrifugal filtration equipment, the concentrator, [...], biological fermentation tank, drying apparatus, the drying apparatus comprises an outer cylinder, the drying cylinder, the inner cylinder; the bottom surface of the outer cylinder is provided with a motor, the rotation of the motor shaft is provided with a exhaust fan blade, type impeller, vortex impeller; exhaust fan leaf is arranged on the bottom surface of the drying cylinder between the cylinder and the outer cylinder; drum type impeller is arranged on the drying cylinder between the cylinder and an inner cylinder; vortex impeller is arranged on the bottom of the inner drum; [...] is set with infrared heating in; on the inner end center provided with a feed port; the outer tube side wall comprises an inner wall and the outer wall; the inner wall and the outer wall of the annular cavity formed between the interlayer; outlet at upper end of the sandwich cavity is provided with an annular baffle plate; the baffle plate is provided with a vent; the upper end of the baffle is provided with a rotatable air purifies the link. This invention can reduce the methylprednisolone intermediate product in the production process of the preparation time, realize methylprednisolone rapid high-quality production. (by machine translation)

Process and intermediates for the preparation of 17 alphahydroxyprogesterones and corticoids from an enol steroid

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