21-acetoxy-11β-hydroxy-6α-methyl-pregna-1,4,17(20)c-trien-3-one
methylprednisolone acetate
Conditions | Yield |
---|---|
With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; tert-butyl alcohol Reagens 4: Pyridin; |
Conditions | Yield |
---|---|
With pyridine |
17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione
A
Methylprednisolone
B
methylprednisolone acetate
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
methylprednisolone acetate
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
methylprednisolone acetate
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
methylprednisolone acetate
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
methylprednisolone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic acid; tert-butyl alcohol; selenium dioxide 2: aqueous formic acid 3: pyridine View Scheme |
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
methylprednisolone acetate
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 |
methylprednisolone acetate
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
methylprednisolone acetate
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
methylprednisolone acetate
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
methylprednisolone acetate
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
methylprednisolone acetate
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
methylprednisolone acetate
methylprednisolone acetate
methylprednisolone acetate
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 |
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
acetic acid
methylprednisolone acetate
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; |
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
methylprednisolone acetate
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
methylprednisolone acetate
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 |
methylprednisolone acetate
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 |
Conditions | Yield |
---|---|
Hydrolysis; | |
With potassium hydroxide In methanol; dichloromethane at 10 - 15℃; for 0.333333h; Inert atmosphere; |
methylprednisolone acetate
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
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
A
Methylprednisolone
B
17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence; |
methylprednisolone acetate
A
11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione
B
11β-hydroxy-6α-methyl-1,4-androstadiene-3,17-dione
Conditions | Yield |
---|---|
Product distribution; Rate constant; Irradiation; radiolytic degradation; |
methylprednisolone acetate
9-fluoro-11β,17,21-trihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione
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
9,21-difluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione
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
21-acetoxy-9-fluoro-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione
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
21-acetoxy-9-bromo-11β,17-dihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-bromo-acetamide; pyridine 2: CH2Cl2; tert-butyl alcohol; aqueous HClO4 View Scheme |
methylprednisolone acetate
21-acetoxy-9,11β-epoxy-17-hydroxy-6α-methyl-9β-pregna-1,4-diene-3,20-dione
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
17α,21-dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Hydrolysis 2: N-bromo-acetamide; pyridine View Scheme |
methylprednisolone acetate
21-acetoxy-17-hydroxy-6α-methyl-11β-trifluoroacetoxy-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
With trifluoroacetic anhydride In pyridine; dichloromethane |
methylprednisolone acetate
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
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 |
Molecular Structure of Methylprednisolone acetate (CAS NO.53-36-1):
Molecular Formula: C24H32O6
Molecular Weight: 416.56
IUPAC Name: [2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-Dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
Classification Code: Anti-Inflammatory Agents ; Drug / Therapeutic Agent ; Glucocorticoid ; Hormone ; Reproductive Effect
EINECS: 200-171-3
Product Categories: Miscellaneous Biochemicals; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids
Index of Refraction: 1.58
Molar Refractivity: 109.67 cm3
Molar Volume: 329.3 cm3
Surface Tension: 54.1 dyne/cm
Density: 1.26 g/cm3
Melting Point: 206°C
Boiling Point: 582.5 °C at 760 mmHg
Flash Point: 196.5 °C
Appearance: Off-White Solid
Vapour Pressure of Methylprednisolone acetate (CAS NO.53-36-1): 5.41E-16 mmHg at 25 °C
Methylprednisolone acetate (CAS NO.53-36-1) can be used as Glucocorticoid
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 1409mg/kg (1409mg/kg) | Drugs in Japan Vol. -, Pg. 1182, 1990. | |
mouse | LD50 | subcutaneous | 1320mg/kg (1320mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES | Journal of Toxicological Sciences. Vol. 10(Suppl, |
rat | LD50 | oral | > 10gm/kg (10000mg/kg) | Drugs in Japan Vol. -, Pg. 1182, 1990. | |
rat | LD50 | subcutaneous | 265mg/kg (265mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES | Journal of Toxicological Sciences. Vol. 10(Suppl, |
Poison by subcutaneous route. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. A steroid. When heated to decomposition it yields acrid smoke and fumes.
Methylprednisolone acetate (CAS NO.53-36-1), its Synonyms are 11beta,17,21-Trihydroxy-6alpha-methylpregna-1,4-diene-3,20-
dione 21-acetate ; 6alpha-Methylprednisolone 21-acetate ; 6alpha-Methylprednisolone acetate ; D-Med ; Demethyl ; Depo-Medrate ; Depo-Medrin ; Depo-Medrol ; Depo-Medrone ; Depo-Methylprednisolone acetate ; Depometicort ; Medrol Enpak ; Medrol acetate ; Mepred ; Methylprednisolone 21-acetate .
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