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52-21-1 Usage

Chemical Properties

White or almost white, crystalline powder.

Originator

Sterane, Phipharmex ,US ,1955

Uses

Synthetic corticosteroid; metabolically interconvertible with prednisone.

Manufacturing Process

To a solution of 0.85 gram of 1,4-pregnadiene-11β,17α,21-triol-3,20-dione (prednisolone) in 5 ml of pyridine are added 3 ml of acetic anhydride. The reaction mixture is allowed to stand at room temperature overnight and is then diluted with ice water. The resulting precipitate is filtered from the mixture and recrystallized from acetone-hexane. There is recovered 0.45 gram of 1,4-pregnadiene-11β,17α,21-triol-3,20-dione 21-acetate, MP 235°239°C. On recrystallization, the MP rose to 237°-239°C.

Brand name

Econopred (Alcon); Meticortelone (Schering); Omnipred (Alcon); Sterane (Pfizer).

Therapeutic Function

Glucocorticoid

Biological Activity

Prednisolone Acetate (Omnipred) is a synthetic corticosteroid that is a particularly potent immunosuppressant.

Clinical Use

For rheumatoid arthritis, rheumatic fever, lupus erythematosus, scleroderma, dermatomyositis, acute lymphoblastic leukemia, etc.

Purification Methods

Recrystallise prednisolone acetate from EtOH, Me2CO, Me2CO/hexane, and it has UV with max at 243nm in EtOH. [Joly et al. Bull Soc Chim Fr 366 1958; Herzog et al. J Am Chem Soc 77 4781 1955, Beilstein 8 IV 3468.]

Check Digit Verification of cas no

The CAS Registry Mumber 52-21-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 2 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 52-21:
(4*5)+(3*2)+(2*2)+(1*1)=31
31 % 10 = 1
So 52-21-1 is a valid CAS Registry Number.
InChI:InChI=1/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h6,8,10,16-18,20,26,28H,4-5,7,9,11-12H2,1-3H3/t16?,17?,18-,20?,21?,22-,23-/m0/s1

52-21-1 Well-known Company Product Price

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  • Sigma-Aldrich

  • (Y0000582)  Prednisolone acetate for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 52-21-1

  • Y0000582

  • 1,880.19CNY

  • Detail

52-21-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Prednisolone Acetate

1.2 Other means of identification

Product number -
Other names Prednisolone acetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:52-21-1 SDS

52-21-1Synthetic route

prednisolon
50-24-8

prednisolon

acetic anhydride
108-24-7

acetic anhydride

prednisolone 21-acetate
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;
21-acetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione
4224-31-1

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

prednisolone 21-acetate
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%
hydrocortisone acetate
50-03-3

hydrocortisone acetate

A

prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

B

21,21'-diacetoxy-11β,17,11'β,17'-tetrahydroxy-2,2'-diselanediyl-bis-pregna-1,4-diene-3,20-dione
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
21-acetoxy-11β-hydroxy-pregna-1,4,17(20)c-trien-3-one
28449-43-6

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

prednisolone 21-acetate
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

prednisolone 21-acetate
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

prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

Conditions
ConditionsYield
With lithium carbonate; N,N-dimethyl-formamide; lithium bromide
21-acetoxy-9-chloro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione
24916-88-9

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

prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

oxone

oxone

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

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

Oxone

Oxone

ethylene glycol
107-21-1

ethylene glycol

A

prednisolon
50-24-8

prednisolon

B

prednisolone 21-acetate
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

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

Oxone

Oxone

prednisolone 21-acetate
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
21-acetoxy-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione disemicarbazone
96580-08-4

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

prednisolone 21-acetate
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
prednisone acetate
125-10-0

prednisone acetate

prednisolone 21-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
pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate
4380-55-6

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

prednisolone 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
(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
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

prednisolone 21-acetate
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
methanol
67-56-1

methanol

prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

A

prednisolon
50-24-8

prednisolon

B

acetic acid methyl ester
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%
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

prednisone 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
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

prednisolon
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
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

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
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%
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

lumiprednisolone 21-acetate
73454-02-1

lumiprednisolone 21-acetate

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

prednisolone 21-acetate

A

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
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

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

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

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
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 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
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

A

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
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

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
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

C23H32O7
73398-05-7

C23H32O7

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

prednisolone 21-acetate

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
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%
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

20,21-epoxy-11β,17,22-trihydroxy-23,24-dinor-20ξH-chola-1,4-dien-3-one
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
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

21-acetoxy-11β,17-dihydroxy-pregna-1,5-diene-3,20-dione
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;
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

21-acetoxy-1α,5-disulfanediyl-11β,17-dihydroxy-5α-pregnane-3,20-dione
115231-00-0

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

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

prednisolone 21-acetate

triethyl phosphite
122-52-1

triethyl phosphite

O21-Acetyl-1-diaethoxyphosphinyl-hydrocortisol
14413-10-6

O21-Acetyl-1-diaethoxyphosphinyl-hydrocortisol

Conditions
ConditionsYield
With phenol
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

A

(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
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

prednisone acetate
125-10-0

prednisone acetate

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

prednisolone 21-acetate

(20R)-21-acetoxy-11β,17,20-trihydroxy-3-oxo-1,4-pregnadiene
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
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

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
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
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

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

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

Conditions
ConditionsYield
Multistep reaction;
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

acetic anhydride
108-24-7

acetic anhydride

11β-Acetoxy-1.17.21-trihydroxy-4-methyl-19-nor-pregna-1.3.5(10)-trien-20-on
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;
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

acetic anhydride
108-24-7

acetic anhydride

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

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

Conditions
ConditionsYield
With perchloric acid
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

21-acetoxy-17-hydroxy-5,11-dioxo-de-A-pregnane-10aα-carbaldehyde
102378-22-3

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

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

prednisolone 21-acetate

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

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;
prednisolone 21-acetate
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

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;
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

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

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;

52-21-1Relevant articles and documents

Preparation method of prednisolone acetate

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, (2021/02/20)

The invention relates to prednisolone acetate and a preparation method of prednisolone acetate, which are characterized in that the prednisolone acetate is prepared by sequentially carrying out a biological fermentation, an esterification reaction, a bromination reaction and a debromination reaction on the raw material, the prednisolone acetate is subjected to a hydrolysis reaction to obtain prednisolone, the overall yield is up to 81.75%, and the HPLC area normalization content of prednisolone is up to 99.5%. The preparation method is short in synthetic route and low in cost, is suitable forindustrial production, and has a very high industrial value.

Optimization of the synthesis of a key intermediate for the preparation of glucocorticoids

Jouve, Romain,Thery, Vincent,Ducki, Sylvie,Helfenbein, Julie,Thiery, Jean-Christophe,Job, Aurélie,Picard, Elodie,Mallet, Christophe,Ripoche, Isabelle,Bennis, Khalil

, p. 14 - 21 (2018/08/01)

A short and efficient synthesis, based on a one-step double elimination, of a key intermediate in the synthesis of various glucocorticosteroids has been developed. This method can be carried out on large scale for further industrial applications. The synthesis allowed us to identify a novel prednisolone derivative 10 and its anti-inflammatory activity was determined in an in vivo model of inflammation. In order to understand the regioselectivity of the double elimination under various conditions, mechanistic studies were undertaken and confirmed the experimental results. We also propose a mechanism for the formation of the new steroid 10 studied by molecular modeling.

Preparation process of prednisolone acetate

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Paragraph 0018; 0019; 0020, (2017/08/28)

The invention relates to a preparation process of prednisolone acetate. The preparation process comprises the steps that under the action of 4-dimethylamino-pyridine, no solvent needs to be additionally added, prednisolone and acetic anhydride directly react, the materials are flushed into water for separation, filtering and drying are carried out, and prednisolone acetate is prepared. The technical prejudice that in the prior art of the reaction process, pyridine or a pyridine-substituted solvent is generally used is overcome, the lot production capacity of a reaction still is greatly improved, and it is avoided that a large amount of industrial waste water hard to treat is generated. The process is simple in process, beneficial to environmental protection, low in cost and suitable for industrial large-scale production.

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