125-10-0

Basic information

• Product Name: Prednisone 21-acetate
• Synonyms: 11,20-trione,21-(acetyloxy)-17-hydroxy-pregna-4-diene-3;4-diene-3,11,20-trione,17,21-dihydroxy-pregna-21-acetate;delcortin;delta’-dehydrocortisoneacetate;delta-corlin;deltalone;nisone;ACETIC ACID 2-((8S,9S,10R,13S,14S,17R)-17-HYDROXY-10,13-DIMETHYL-3,11-DIOXO-6,7,8,9,10,11,12,13,14,15,16,17-DODECAHYDRO-3H-CYCLOPENTA[A]PHENANTHREN-17-YL)-2-OXO-ETHYL ESTER
• CAS NO: 125-10-0
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.46
• EINECS: 204-726-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 125-10-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 240-242°C (dec.)
• Boiling Point: 582 °C at 760 mmHg
• Flash Point: 200.2 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 5.69E-16mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Dioxane (Sparingly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.31±0.60(Predicted)
• Water Solubility: 23mg/L(25 oC)
• CAS DataBase Reference: Prednisone 21-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Prednisone 21-acetate(125-10-0)
• EPA Substance Registry System: Prednisone 21-acetate(125-10-0)

Safety Data

• Hazardous Substances Data: 125-10-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Adrenocortical steroid antiinflammatory.

InChI:InChI=1/C23H28O6/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/h6,8,10,16-17,20,28H,4-5,7,9,11-12H2,1-3H3/t16?,17?,20?,21?,22?,23-/m0/s1

Synthetic route

prednisolone 21-acetate (52-21-1) → prednisone acetate (125-10-0)

Conditions	Yield
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

21-acetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione (4224-31-1) → prednisone acetate (125-10-0)

Conditions	Yield
With tert-Butyl peroxybenzoate Inert atmosphere; Reflux;	81%

Cortisone acetate (50-04-4) → prednisone acetate (125-10-0)

Conditions	Yield
With selenium(IV) oxide
With periodic acid
With iodine pentoxide
With Arthrobacter simplex By-2-13	17 g

prednisolone 21-acetate (52-21-1) → (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) + prednisone acetate (125-10-0)

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

21-acetoxy-17-hydroxy-5α(or β)-pregn-1-ene-3,11,20-trione → prednisone acetate (125-10-0)

Conditions	Yield
With selenium(IV) oxide
With iodine pentoxide; periodic acid

21-acetoxy-17-hydroxy-5α(or β)-pregnane-3,11,20-trione → prednisone acetate (125-10-0)

Conditions	Yield
With selenium(IV) oxide
With iodine pentoxide; periodic acid
Bromierung und Erhitzen mit 2,4,6-Trimethyl-pyridin;

Prednison (53-03-2) + acetic anhydride (108-24-7) → prednisone acetate (125-10-0)

Conditions	Yield
In pyridine

prednisolon (50-24-8) → prednisone acetate (125-10-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: CrO3 View Scheme

21-acetoxy-11β-hydroxy-pregna-1,4,17(20)c-trien-3-one (28449-43-6) → prednisone acetate (125-10-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: diacetoxyiodanyl-benzene 2: N-bromo-acetamide View Scheme

hydrocortisone acetate (50-03-3) → prednisone acetate (125-10-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; manganese(ll) chloride; chromium(VI) oxide / water; chloroform / 30 °C 2: Arthrobacter simplex By-2-13 View Scheme

prednisone acetate (125-10-0) + acetic acid (64-19-7) → 17α,21-diacetoxypregna-1,4-diene-3,11,20-trione (6677-19-6)

Conditions	Yield
With trifluoroacetic anhydride; toluene-4-sulfonic acid at 0 - 20℃; for 3.5h;	100%
With toluene-4-sulfonic acid; trifluoroacetic anhydride at 0 - 20℃; for 3.5h; Cooling with ice;	100%
With toluene-4-sulfonic acid; trifluoroacetic anhydride at 0 - 20℃; for 3.5h;	100%

prednisone acetate (125-10-0) → Prednison (53-03-2)

Conditions	Yield
With di(n-butyl)tin oxide In methanol for 4h; Heating;	89%
Stage #1: prednisone acetate With potassium carbonate In ethanol; water at 15℃; Stage #2: With acetic acid In ethanol; water Solvent; Reagent/catalyst; Temperature;	68.5%
With potassium hydrogencarbonate
With potassium hydroxide
With sodium methylate

prednisone acetate (125-10-0) → 21-acetoxy-1,4,16-pregnatriene-3,11,20-trione (82423-35-6)

Conditions	Yield
Stage #1: prednisone acetate With pyridine; N-chloro-succinimide; sulfur dioxide at 15℃; for 1h; Large scale; Stage #2: With hydrogenchloride In water at 0℃; for 5h; Temperature; Large scale;	83.5%

prednisone acetate (125-10-0) → 21-Acetoxy-1α,2α-epoxy-17α-hydroxy-4-pregnene-1,11,20-trione (139016-49-2)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone at 20℃; for 20h; Mechanism; other substrates; methyl(trifluoromethyl)dioxirane as reagent;	80%
With 3,3-dimethyldioxirane In acetone at 20℃; for 20h;	80%

prednisone acetate (125-10-0) → 21-Acetoxy-1α,2α-epoxy-17α-hydroxy-4-pregnene-1,11,20-trione (139016-49-2) + 21-Acetoxy-4α,5α-epoxy-17α-hydroxy-1-pregnene-3,11,20-trione + 21-Acetoxy-4β,5β-epoxy-17α-hydroxy-1-pregnene-3,11,20-trione

Conditions	Yield
With 3,3-dimethyldioxirane In dichloromethane; acetone at 20℃; for 20h;	A 80% B 4 % Spectr. C 16 % Spectr.
With 3,3-dimethyldioxirane In dichloromethane; acetone at 20℃; for 20h; Title compound not separated from byproducts;	A 80% B 4 % Spectr. C 16 % Spectr.

prednisone acetate (125-10-0) + 3,3-dimethyldioxirane (74087-85-7) → 21-Acetoxy-1α,2α-epoxy-17α-hydroxy-4-pregnene-1,11,20-trione (139016-49-2)

Conditions	Yield
In acetone at 23℃; Kinetics;	73%

2-furancarbonyl chloride (527-69-5) + prednisone acetate (125-10-0) → Furan-2-carboxylic acid (8S,9S,10R,13S,14S,17R)-17-(2-acetoxy-acetyl)-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester (94813-60-2)

Conditions	Yield
With dmap In dichloromethane for 72h;	35%

diazomethane (186581-53-3, 908094-01-9) + prednisone acetate (125-10-0) → (20Ξ)-20,21-epoxy-17-hydroxy-20-hydroxymethyl-pregna-1,4-diene-3,11-dione (111162-85-7)

Conditions	Yield
With methanol; diethyl ether

thioacetic acid (507-09-5) + prednisone acetate (125-10-0) → 21-acetoxy-1α-acetylsulfanyl-17-hydroxy-pregn-4-ene-3,11,20-trione (124107-03-5)

Conditions	Yield
Irradiation.mit UV-Licht;

prednisone acetate (125-10-0) → 21-acetoxy-17-hydroxy-5,11-dioxo-de-A-pregnane-10aα-carbaldehyde (102378-22-3)

Conditions	Yield
With ozone
(i) O3, AcOEt, (ii) H2O; Multistep reaction;

prednisone acetate (125-10-0) → 21-acetoxy-17-hydroxy-1,5β-cyclo-1,10-seco-pregna-3,9-diene-2,11,20-trione (72011-93-9)

Conditions	Yield
With 1,4-dioxane Irradiation.UV-Licht;
With ethanol Irradiation.UV-Licht;

prednisone acetate (125-10-0) → 21-acetoxy-10,17-dihydroxy-1αH,10αH-1,5-cyclo-5,10-seco-pregn-4-ene-3,11,20-trione (72779-19-2)

Conditions	Yield
With acetic acid Irradiation.mit UV-Licht;

prednisone acetate (125-10-0) → 21-acetoxy-6ξ-bromo-17-hydroxy-pregna-1,4-diene-3,11,20-trione (21365-82-2)

Conditions	Yield
With N-Bromosuccinimide

prednisone acetate (125-10-0) → lumiprednisone 21-acetate (73397-96-3)

Conditions	Yield
Photoisomerisierung;
With ethanol Irradiation.UV-Licht;

prednisone acetate (125-10-0) → 21-acetoxy-1α,5-disulfanediyl-17-hydroxy-5α-pregnane-3,11,20-trione (114982-44-4)

Conditions	Yield
With pyridine; hydrogen sulfide; sulfur

prednisone acetate (125-10-0) + triethyl phosphite (122-52-1) → O21-Acetyl-1-diaethoxyphosphinyl-cortison (14413-09-3)

Conditions	Yield
With phenol

prednisone acetate (125-10-0) + acetic anhydride (108-24-7) → 3,17,21-Triacetoxy-1-methyl-19-norpregna-1,3.5(10)-trien-11,20-dion (103004-64-4)

Conditions	Yield
With perchloric acid

prednisone acetate (125-10-0) + acetic anhydride (108-24-7) → 1-Methyl-3.11β.17α.21-tetrahydroxy-19-nor-pregna-1.3.5(10).9(11)-tetraen-20-on-tetraacetat (13396-30-0)

Conditions	Yield
With sulfuric acid
With perchloric acid

prednisone acetate (125-10-0) → 1α,2α,17α-Trihydroxy-21-acetoxy-Δ4-pregnantrion-(3,11,20) (14945-34-7)

Conditions	Yield
With osmium(VIII) oxide
With pyridine; osmium(VIII) oxide

prednisone acetate (125-10-0) → 21-Acetoxy-17α-hydroxy-5,10-seco-1,2,3,4-tetrakis-norpregnan-5,11,20-trion

Conditions	Yield
(i) O3, AcOEt, (ii) H2O, (iii) aq. H3PO3, AcOH; Multistep reaction;

prednisone acetate (125-10-0) → 14C-21-Acetoxy-1α,17α-dihydroxy-2-oxa-pregn-4-en-3,11,20-trion

Conditions	Yield
(i) O3, AcOEt, (ii) H2O; Multistep reaction;

prednisone acetate (125-10-0) → 21-acetoxy-2,17-dihydroxy-1-methyl-19-nor-pregna-1,3,5(10)-triene-11,20-dione (72011-85-9) + O21-acetyl-isolumiprednisone

Conditions	Yield
With 1,4-dioxane Irradiation.UV-Licht;

Upstream product

• 50-04-4 Cortisone acetate 
• 52-21-1 prednisolone 21-acetate 
• 53-03-2 Prednison 
• 108-24-7 acetic anhydride 
• 50-03-3 hydrocortisone acetate 
• 4224-31-1 21-acetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione 
• 28449-43-6 21-acetoxy-11β-hydroxy-pregna-1,4,17(20)c-trien-3-one 
• 50-24-8 prednisolon 

Downstream Products

• 53-03-2 Prednison 
• 6677-19-6 17α,21-diacetoxypregna-1,4-diene-3,11,20-trione 
• 82423-35-6 21-acetoxypregna-1,4,16-triene-3,11,20-trione 
• 52-21-1 prednisolone 21-acetate 
• 14411-14-4 1α,1β,17α-Trihydroxy-21-acetoxy-A-nor-Δ³⁽⁵⁾-pregnentrion-(2,11,20) 
• 83291-83-2 Acetic acid 2-((4aR,4bS,5S,6aS,6bR,9aS,10aS,10bS)-8-benzyl-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,8,9,9a,10,10a,10b,11,12-tetradecahydro-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester 
• 3044-42-6 21-acetoxy-11β-hydroxyl-1,4,16-pregnatriene-3,20-dione 

Relevant articles and documents

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