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52-21-1

Basic Information
CAS No.: 52-21-1
Name: Pregna-1,4-diene-3,20-dione,21-(acetyloxy)-11,17-dihydroxy-, (11b)-
Molecular Structure:
Molecular Structure of 52-21-1 (Pregna-1,4-diene-3,20-dione,21-(acetyloxy)-11,17-dihydroxy-, (11b)-)
Formula: C23H30O6
Molecular Weight: 402.53
Synonyms: Supercortyl;Prednisolone acetate;Prednidoren;Predicort;Pred-Forte;Pregna-1,4-diene-3,20-dione,11b,17,21-trihydroxy-, 21-acetate(6CI,7CI,8CI);11b,17a,21-Trihydroxypregna-1,4-diene-3,20-dione21-acetate;21-Acetoxy-11b,17-dihydroxypregna-1,4-diene-3,20-dione;Cormalone;Deltilen;Econopred;Falcon (steroid);Inflanefran;Meticortelone acetate;NSC 10966;Pred Mild;
EINECS: 200-134-1
Density: 1.28 g/cm3
Melting Point: 240-244 °C
Boiling Point: 579.8 °C at 760 mmHg
Flash Point: 198.4 °C
Solubility: 11.6mg/L(25 oC)
Appearance: white crystalline powder
Hazard Symbols: ToxicT,CorrosiveC,FlammableF
Risk Codes: 25-34-11
Safety: 45-36/37/39-26-16
Transport Information: UN 2811 6.1/PG 3
PSA: 100.90000
LogP: 2.12840
Synthetic route
50-24-8

prednisolon

108-24-7

acetic anhydride

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 40℃; for 0.5h; Inert atmosphere;99.8%
With pyridine98%
With pyridine
With dmap at 60 - 65℃; for 6h; Time;55.1 g
With sodium acetate In tetrahydrofuran; acetone at 40℃; for 3h; Reagent/catalyst; Inert atmosphere;
4224-31-1

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

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
Stage #1: 21-acetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione With chromium(VI) oxide; mercaptoacetic acid; zinc In dimethyl sulfoxide; acetone at 15 - 20℃;
Stage #2: With hydrogenchloride In water for 1h;
Stage #3: With sodium thiosulfate In water for 0.333333h; Reagent/catalyst;
92%
50-03-3

hydrocortisone acetate

A

52-21-1

prednisolone 21-acetate

B

120612-05-7

21,21'-diacetoxy-11β,17,11'β,17'-tetrahydroxy-2,2'-diselanediyl-bis-pregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With selenium(IV) oxide; acetic acid
28449-43-6

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

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene
21-acetoxy-1117β-dihydroxy-pregn-4-en-3,20-one

21-acetoxy-1117β-dihydroxy-pregn-4-en-3,20-one

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
With selenium(IV) oxide
With iodine pentoxide
21-acetoxy-2α,4β-dibromo-11β,17-dihydroxy-5pregnane-3,20-dione

21-acetoxy-2α,4β-dibromo-11β,17-dihydroxy-5pregnane-3,20-dione

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
With lithium carbonate; N,N-dimethyl-formamide; lithium bromide
24916-88-9

21-acetoxy-9-chloro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione

52-21-1

prednisolone 21-acetate

oxone

oxone

11β,17α-dihydroxy-20-phenoxypregna-1,4,20-trien-3-one

Oxone

Oxone

107-21-1

ethylene glycol

A

50-24-8

prednisolon

B

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
With potassium hydroxide; sodium hydroxide In tetrahydrofuran; PO4; dichloromethane; water; acetone
oxone

oxone

11β,17α-dihydroxy-20-phenoxypregna-1,4,20-trien-3-one

Oxone

Oxone

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
With dmap; potassium hydroxide; sodium hydroxide; acetic anhydride; triethylamine In tetrahydrofuran; PO4; dichloromethane; water; acetone
With dmap; potassium hydroxide; sodium hydroxide; acetic anhydride; triethylamine In tetrahydrofuran; PO4; n-heptane; dichloromethane; water; acetone
96580-08-4

21-acetoxy-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione disemicarbazone

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
Stage #1: 21-acetoxy-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione disemicarbazone With hydrogenchloride In chloroform; water at 25 - 30℃; for 0.5h;
Stage #2: With sodium nitrite In chloroform; water at 18 - 22℃; for 6h;
19.5 g
125-10-0

prednisone acetate

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
Stage #1: prednisone acetate With sodium acetate; acetic anhydride; acetic acid In acetone for 4h; Reflux;
Stage #2: With hydrogenchloride In chloroform; water at 25 - 30℃; for 0.5h;
Stage #3: With sodium nitrite In chloroform; water at 18 - 22℃; for 3h; Reagent/catalyst;
21.8 g
4380-55-6

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid / acetone; water / 0.5 h / 0 - 5 °C
1.2: 0 - 5 °C
2.1: zinc; chromium(VI) oxide; mercaptoacetic acid / acetone; dimethyl sulfoxide / 15 - 20 °C
2.2: 1 h
2.3: 0.33 h
View Scheme
10184-69-7

(10S,13S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one

52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dmap / chloroform / 0.17 h
1.2: 10 - 20 °C
2.1: sulfuric acid / acetone; water / 0.5 h / 0 - 5 °C
2.2: 0 - 5 °C
3.1: zinc; chromium(VI) oxide; mercaptoacetic acid / acetone; dimethyl sulfoxide / 15 - 20 °C
3.2: 1 h
3.3: 0.33 h
View Scheme
67-56-1

methanol

52-21-1

prednisolone 21-acetate

A

50-24-8

prednisolon

B

79-20-9

acetic acid methyl ester

Conditions
ConditionsYield
With triethylamine at 20℃; under 8250660 Torr; for 2h; Product distribution;A n/a
B 100%
52-21-1

prednisolone 21-acetate

125-10-0

prednisone acetate

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In N,N-dimethyl-formamide at 23 - 25℃; for 5h;99%
With 1-hydroxy-1.oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one pyridinium salt In N,N-dimethyl-formamide at 24 - 28℃; for 4h;97%
With N-bromoacetamide
With chromium(VI) oxide
52-21-1

prednisolone 21-acetate

50-24-8

prednisolon

Conditions
ConditionsYield
With water; potassium carbonate; sodium hydroxide In methanol at 0 - 10℃; for 2h; Inert atmosphere;92.5%
With methanol; triethylamine for 14h; Ambient temperature;49%
With potassium hydroxide
Stage #1: prednisolone 21-acetate With water; sodium hydroxide In methanol; dichloromethane at 0 - 30℃; for 2.5h; Inert atmosphere;
Stage #2: With acetic acid In methanol; dichloromethane at -12 - -5℃; for 1h; pH=6 - 7; Reagent/catalyst; Reflux;
15.8 g
52-21-1

prednisolone 21-acetate

37413-91-5

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

Conditions
ConditionsYield
Stage #1: prednisolone 21-acetate With pyridine; N-chloro-succinimide at -15 - 20℃; for 0.416667h; Inert atmosphere;
Stage #2: With sulfur dioxide for 1h; Inert atmosphere;
83.5%
52-21-1

prednisolone 21-acetate

73454-02-1

lumiprednisolone 21-acetate

Conditions
ConditionsYield
In 1,4-dioxane for 3.5h; Irradiation;78%
52-21-1

prednisolone 21-acetate

A

37413-91-5

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

B

4380-55-6

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate

C

2-((10S)-10,17-dimethyl-3-oxo-6,7,8,10,12,15,16,17-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

D

C46H54O11S

Conditions
ConditionsYield
With pyridine; thionyl chloride In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Temperature;A 50%
B n/a
C n/a
D n/a
52-21-1

prednisolone 21-acetate

4380-55-6

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate

Conditions
ConditionsYield
With N,N'-Thionyldiimidazole In tetrahydrofuran for 0.5h; Ambient temperature;41%
With pyridine; methanesulfonyl chloride
52-21-1

prednisolone 21-acetate

A

73398-00-2

Acetic acid 2-oxo-2-((3R,3aS,5S,5aR,6S,6aR,11aS,11bS)-3,5,6-trihydroxy-3a,6-dimethyl-8-oxo-2,3,3a,4,5,5a,6,6a,7,8,10,11,11a,11b-tetradecahydro-1H-indeno[5,4-f]azulen-3-yl)-ethyl ester

B

73398-10-4

Acetic acid 2-((3aS,4aS,5aS,6R,8aS,8bS,10bS,10cS)-6-hydroxy-5a,10b-dimethyl-3-oxo-3,3a,4a,5,5a,6,7,8,8a,8b,9,10,10b,10c-tetradecahydro-2H-4-oxa-dicyclopenta[a,def]phenanthren-6-yl)-2-oxo-ethyl ester

C

73398-05-7

C23H32O7

Conditions
ConditionsYield
In acetic acid for 2.5h; Irradiation;A 20.1%
B 38.5%
C 19.2%
52-21-1

prednisolone 21-acetate

134526-05-9

Acetic acid 2-oxo-2-((6S,8S,9S,10R,11S,13S,14S,17R)-6,11,17-trihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-ethyl ester

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane at 110℃; for 28h;21.5%
52-21-1

prednisolone 21-acetate

102958-04-3

20,21-epoxy-11β,17,22-trihydroxy-23,24-dinor-20ξH-chola-1,4-dien-3-one

Conditions
ConditionsYield
With methanol; diethyl ether
52-21-1

prednisolone 21-acetate

112441-85-7

21-acetoxy-11β,17-dihydroxy-pregna-1,5-diene-3,20-dione

Conditions
ConditionsYield
With 1,4-dioxane; bromine; acetic acid Erwaermen des Reaktionsprodukts mit Zink und wss.Aethanol;
52-21-1

prednisolone 21-acetate

115231-00-0

21-acetoxy-1α,5-disulfanediyl-11β,17-dihydroxy-5α-pregnane-3,20-dione

Conditions
ConditionsYield
With pyridine; hydrogen sulfide; sulfur
52-21-1

prednisolone 21-acetate

122-52-1

triethyl phosphite

14413-10-6

O21-Acetyl-1-diaethoxyphosphinyl-hydrocortisol

Conditions
ConditionsYield
With phenol
52-21-1

prednisolone 21-acetate

A

898-84-0

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione

B

125-10-0

prednisone acetate

Conditions
ConditionsYield
Product distribution; Rate constant; Irradiation; radiolytic degradation;
52-21-1

prednisolone 21-acetate

96346-38-2

(20R)-21-acetoxy-11β,17,20-trihydroxy-3-oxo-1,4-pregnadiene

Conditions
ConditionsYield
With sodium tetrahydroborate In N,N-dimethyl-formamide for 3h; Ambient temperature;235 mg
52-21-1

prednisolone 21-acetate

71826-43-2

Acetic acid 2-((8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-thioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

Conditions
ConditionsYield
With pyridine; tetraphosphorus decasulfide
52-21-1

prednisolone 21-acetate

11α-Hydroxy-1-methoxy-4-methyl-oestra-1,3,5(10)-trien-17-on

Conditions
ConditionsYield
Multistep reaction;
52-21-1

prednisolone 21-acetate

108-24-7

acetic anhydride

53771-09-8

11β-Acetoxy-1.17.21-trihydroxy-4-methyl-19-nor-pregna-1.3.5(10)-trien-20-on

Conditions
ConditionsYield
(i) aq. HClO4, (ii) NaOMe, aq. AcOH; Multistep reaction;
52-21-1

prednisolone 21-acetate

108-24-7

acetic anhydride

1.11β.17.21-Tetraacetoxy-4-methyl-19-nor-pregna-1.3.5(10)-trien-20-on

Conditions
ConditionsYield
With perchloric acid
52-21-1

prednisolone 21-acetate

102378-22-3

21-acetoxy-17-hydroxy-5,11-dioxo-de-A-pregnane-10aα-carbaldehyde

Conditions
ConditionsYield
(i) O3, AcOEt, (ii) H2O; Multistep reaction;
52-21-1

prednisolone 21-acetate

1178-19-4

4α,5α,11β,17α,21-Pentahydroxy-pregn-1-en-3,20-dion-21-acetat

Conditions
ConditionsYield
(i) OsO4, Py, (ii) H2S, dioxane, CHCl3; Multistep reaction;
52-21-1

prednisolone 21-acetate

Acetic acid 2-{(1R,3aS,4S,5S,6aS)-5-formyl-1-hydroxy-4-[2-(5-hydroxy-2-methyl-phenyl)-ethyl]-6a-methyl-octahydro-pentalen-1-yl}-2-oxo-ethyl ester

Conditions
ConditionsYield
(i) POCl3, THF, (ii) (enzymatic hydrolysis); Multistep reaction;
52-21-1

prednisolone 21-acetate

Phosphoric acid mono-(3-{2-[(1S,2S,3aS,4R,6aS)-2-formyl-4-hydroxy-4-(2-hydroxy-acetyl)-3a-methyl-octahydro-pentalen-1-yl]-ethyl}-4-methyl-phenyl) ester

Conditions
ConditionsYield
(i) POCl3, THF, (ii) aq. K2CO3, MeOH; Multistep reaction;
52-21-1

prednisolone 21-acetate

1255-33-0

1α.2α.11β.17α.21-Pentahydroxy-pregn-4-en-3.20-dion-21-acetat

Conditions
ConditionsYield
(i) OsO4, Py, (ii) H2S, dioxane, CHCl3; Multistep reaction;
52-21-1

prednisolone 21-acetate

Acetic acid 2-{(1R,3aS,4S,5S,6aS)-5-formyl-1-hydroxy-6a-methyl-4-[2-(2-methyl-5-phosphonooxy-phenyl)-ethyl]-octahydro-pentalen-1-yl}-2-oxo-ethyl ester

Conditions
ConditionsYield
(i) POCl3, THF, (ii) aq. NaOH, MeOH; Multistep reaction;
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Chemistry

Product Name: [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-Dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
Empirical Formula: C23H30O6
Molecular Weight: 402.4807
EINECS: 200-134-1 
Index of Refraction: 1.587
Density: 1.28 g/cm3
Flash Point: 198.4 °C
Melting point: 240-244 °C
Appearance: white crystalline powder
Enthalpy of Vaporization: 99.6 kJ/mol
Boiling Point: 579.8 °C at 760 mmHg
Vapour Pressure: 7.36E-16 mmHg at 25 °C
Structure of Prednisolone-21-acetate (CAS NO.52-21-1):
                       
Product Category of Prednisolone-21-acetate (CAS NO.52-21-1): Biochemistry;Hydroxyketosteroids;Steroids

Uses

 Prednisolone-21-acetate (CAS NO.52-21-1) can be applied to rheumatoid arthritis, rheumatic fever, lupus, scleroderma, dermatomyositis, acute lymphatic leukemia, and so on.

Toxicity Data With Reference

1.    

scu-mus TDLo:96 mg/kg (11D preg):TER

    SEIJBO    Senten Ijo. Congenital Anomalies. 13 (1973),245.
2.    

orl-rat TDLo:1800 mg/kg (2-19D preg):REP

    FESTAS    Fertility and Sterility. 22 (1971),735.
3.    

scu-mus LD50:3500 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),713.

Safety Profile

Moderately toxic by subcutaneous route. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes of Prednisolone-21-acetate (CAS NO.52-21-1): ToxicT,CorrosiveC,FlammableF
Risk Statements: 25-34-11
R11:Highly flammable. 
R25 :Toxic if swallowed. 
R34:Causes burns.
Safety Statements: 45-36/37/39-26-16 
S16:Keep away from sources of ignition. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Specification

 Prednisolone-21-acetate , its cas register number is 52-21-1. It also can be called Blephamide liquifilm ; Prednisolone acetate ; and 11b,17,21-Trihydroxypregna-1,4-diene-3,20-dione 21-acetate .