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  • acetic acid [2-[(10R,13S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] ester

    Cas No: 50-04-4

  • No Data

  • 10 Milligram

  • Amadis Chemical Co., Ltd.
  • Contact Supplier
  • 50-04-4 Structure
  • Basic information

    1. Product Name: Cortisone acetate
    2. Synonyms: 11,20-trione,17,21-dihydroxy-pregn-4-ene-21-acetate;11-dehydro-17-hydroxycorticosterone-21-acetate;11-dehydro-17-hydroxycorticosteroneacetate;17,21-dihydroxypregn-4-ene-3,11,20-trioneacetate;20-trione,21-(acetyloxy)-17-hydroxy-pregn-4-ene-11;21-(acetyloxy)-17-hydroxypregn-4-ene-3,11,20-trione;21-acetoxy-17,alpha-hydroxy-3,11,20-triketopregnene-4;21-acetoxy-17,alpha-hydroxypregn-4-ene-3,11,20-trione
    3. CAS NO:50-04-4
    4. Molecular Formula: C23H30O6
    5. Molecular Weight: 402.48
    6. EINECS: 200-006-5
    7. Product Categories: Biochemistry;Hydroxyketosteroids;Steroids;CORTONE;Hormone Drugs;Inhibitors
    8. Mol File: 50-04-4.mol
    9. Article Data: 13
  • Chemical Properties

    1. Melting Point: 237-240 °C(lit.)
    2. Boiling Point: 567.8 °C at 760 mmHg
    3. Flash Point: 311.2 °C
    4. Appearance: solid
    5. Density: 1.28 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 212 ° (C=1, MeOH)
    8. Storage Temp.: 2-8°C
    9. Solubility: Practically insoluble in water, freely soluble in methylene chloride, soluble in dioxan, sparingly soluble in acetone, slightly soluble in ethanol (96 per cent) and in methanol.
    10. PKA: 12.32±0.60(Predicted)
    11. Water Solubility: 19mg/L(25 oC)
    12. Stability: Stable. Incompatible with strong oxidizing agents.
    13. Merck: 14,2539
    14. BRN: 2067543
    15. CAS DataBase Reference: Cortisone acetate(CAS DataBase Reference)
    16. NIST Chemistry Reference: Cortisone acetate(50-04-4)
    17. EPA Substance Registry System: Cortisone acetate(50-04-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-36/37-24/25
    4. WGK Germany: 3
    5. RTECS: GM9140000
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 50-04-4(Hazardous Substances Data)

50-04-4 Usage

Description

Cortisone acetate, also known as 21-(acetyloxy)-17-hydroxypregn-4-ene-3,11,20-trione, is a synthetic glucocorticoid derived from the naturally occurring cortisone. It possesses anti-inflammatory properties and is known for its good systemic anti-inflammatory activity and low-to-moderate salt-retention activity after its in vivo conversion to hydrocortisone acetate. This conversion is mediated by 11β-hydroxysteroid dehydrogenase. Cortisone acetate is a solid and is relatively ineffective topically, mainly because it must be reduced in vivo to hydrocortisone.

Uses

Used in Pharmaceutical Industry:
Cortisone acetate is used as an anti-inflammatory agent for treating various conditions such as collagen diseases, Addison's disease, severe shock, allergic conditions, chronic lymphocytic leukemia, and many other indications. It is bioavailable and readily converted to the therapeutically active form, hydrocortisone.
Used in Dermatological Applications:
Cortisone acetate is used as a topical medication for relieving inflammation and pruritic manifestations of corticosteroid-responsive dermatoses. It is also used in the treatment of immune and allergic disorders.
Used in Veterinary Medicine:
Cortisone acetate is used in rabbits to decrease the size of Bacillus Calmette-Guérin (BCG) vaccine-induced dermal lesions and tuberculin reactions when administered at 2 mg/kg on alternate days over the course of 46 days. It also reduces the number and percentage of activated lesion-infiltrating mononuclear cells and decreases the amount of caseous necrosis and ulceration. Additionally, cortisone acetate (2.5 mg/kg per day, s.c.) slows tissue regeneration in a rabbit model of wound healing.
Used in Research:
Cortisone acetate is used to study its effects on the number of dexamethasone binding sites on isolated human lymphocytes, as it has been shown to decrease these sites by 30%.

Originator

Cortone Acetate,MSD,US,1950

Manufacturing Process

The following technique is described in US Patent 2,541,104. A solution of 2.0 g of 3(α)-hydroxy-21-acetoxy-11,20-diketo-pregnane, which can be prepared as described in Helv. Chim. Acta 27, 1287 (1944), is treated in a mixture of 25 cc of alcohol and 6.4 cc of acetic acid at 0°C with 6.0 g of potassiumcyanide. The solution is allowed to warm to room temperature and after 3 hours is diluted with water. The addition of a large volume of water to the alcohol-hydrogen cyanide mixture precipitates a gum which is extracted with chloroform or ethyl acetate. The extract is washed with water, and evaporated to small volume under reduced pressure. The crystalline precipitate (1.3 g) consists of 3(α),20-dihydroxy-20-cyano-21-acetoxy-11-keto-pregnane; dec. 175° to 185°C.A solution of 0.60 g of chromic acid in 1.2 cc of water and 11 cc of acetic acid is added to a solution containing about 1.2 g of 3(α),20-dihydroxy-20-cyano- 21-acetoxy-11-ketopregnane at room temperature. After 1 hour, water is added and the product, which precipitates, is filtered and recrystallized from ethyl acetate to produce 3,11-diketo-20-hydroxy-20-cyano-21-acetoxypregnane; dec. 214° to 217°C. 0.40 cc of phosphorus oxychloride is added to a solution containing about 950 mg of 3,11-diketo-20-hydroxy-20-cyano-21-acetoxy-pregnane dissolved in 3 cc of pyridine. After standing at room temperature for 24 hours, the solution is poured into water and dilute hydrochloric acid, extracted with benzene and concentrated to dryness. The crude product, after chromatography gives one main constituent, namely δ17-3,11-diketo-20-cyano-21-acetoxy-pregnene; MP 189° to 190°C. A solution of 1.0 g of δ17-3,11-diketo-20-cyano-21-acetoxy-pregnene in 10 cc of benzene is treated with 1.0 g of osmium tetroxide and 0.43 g of pyridine. After standing at room temperature for 18 hours, the resulting solution is treated successively with 50 cc of alcohol, and with 50 cc of water containing 2.5 g of sodium sulfite. The mixture is stirred for 30 hours, filtered, and the filtrate acidified with 0.5 cc of acetic acid and concentrated to small volume in vacuo. The aqueous suspension is then extracted four times with chloroform, the chloroform extracts are combined, washed with water and concentrated to dryness in vacuo. Recrystallization of the residue from acetone gives 9°C. This compound is then treated with acetic anhydride and pyridine for 15 minutes at room temperature to produce 3,11,20-triketo-17(α)-hydroxy-21-acetoxypregnane or cortisone acetate.

Therapeutic Function

Glucocorticoid

Purification Methods

Crystallise -1cortisone-21-acetate from acetone or CHCl3. The UV has 15,800 M-1cm at 238nm in dioxane. [Sarett J Biol Chem 162 601 1946, Beilstein 8 III 4058, 5 IV 3481.]

Check Digit Verification of cas no

The CAS Registry Mumber 50-04-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 50-04:
(4*5)+(3*0)+(2*0)+(1*4)=24
24 % 10 = 4
So 50-04-4 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/h10,16-17,20,28H,4-9,11-12H2,1-3H3/t16-,17-,20+,21+,22+,23+/m1/s1

50-04-4 Well-known Company Product Price

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  • (C2800000)  Cortisone acetate  European Pharmacopoeia (EP) Reference Standard

  • 50-04-4

  • C2800000

  • 1,880.19CNY

  • Detail

50-04-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Cortisone acetate

1.2 Other means of identification

Product number -
Other names 17α,21-Dihydroxy-4-pregnene-3,11,20-trione 21-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:50-04-4 SDS

50-04-4Synthetic route

anecortave
7753-60-8

anecortave

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
Stage #1: anecortave With tetrafluoroboric acid In dichloromethane; acetone at -5 - 0℃; for 5h; Inert atmosphere;
Stage #2: With Jones reagent In dichloromethane; acetone at 0 - 5℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;
95.8%
Acetic acid 2-hydroxy-2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl ester

Acetic acid 2-hydroxy-2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl ester

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 50℃; for 3h;93%
hydrocortisone acetate

hydrocortisone acetate

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate; bis(acetoxy)iodylbenzene In dichloromethane at 20℃; for 0.5h;93%
21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione
50733-54-5

21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With di-tert-butyl peroxide In tetrahydrofuran Inert atmosphere; Reflux;90%
C23H29BrO6

C23H29BrO6

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With acetic acid; zinc In dichloromethane at 10℃; for 3h; Temperature;79.5%
hydrocortisone acetate
50-03-3

hydrocortisone acetate

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
With pyridine; magnesium sulfate; pyridinium chlorochromate at 0 - 25℃; for 12h;
With chromium(VI) oxide; acetic acid; manganese(ll) chloride In chloroform; water at 30℃; Solvent; Reagent/catalyst; Temperature;19.2 g
21-acetoxy-17-hydroxy-5β-pregnane-3,11,20-trione
1499-59-8

21-acetoxy-17-hydroxy-5β-pregnane-3,11,20-trione

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With bromine durch aufeinanderfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure;
21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione
988-16-9

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid
hydrocortisone acetate
50-03-3

hydrocortisone acetate

A

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione
382-44-5

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

B

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
Product distribution; Rate constant; Irradiation; radiolytic degradation;
21-acetoxy-11α,17-dihydroxy-pregn-4-ene-3,20-dione

21-acetoxy-11α,17-dihydroxy-pregn-4-ene-3,20-dione

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With chromium(VI) oxide
21-acetoxy-pregna-4,17(2O)c-diene-3,11-dione

21-acetoxy-pregna-4,17(2O)c-diene-3,11-dione

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With osmium(VIII) oxide; triethylamine N-oxide; dihydrogen peroxide
hydrocortisone acetate
50-03-3

hydrocortisone acetate

acetic acid
64-19-7

acetic acid

CrO3

CrO3

Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-17,20βF-dihydroxy-pregn-4-ene-3,11-dione
111615-16-8

21-acetoxy-17,20βF-dihydroxy-pregn-4-ene-3,11-dione

acetic acid
64-19-7

acetic acid

CrO3

CrO3

A

Cortisone acetate
50-04-4

Cortisone acetate

B

adrenosterone
382-45-6

adrenosterone

HYDROCORTISONE
50-23-7

HYDROCORTISONE

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: CrO3; acetic acid
View Scheme
11α-hydroxy-16α,17α-epoxyprogesterone
3684-83-1, 19427-36-2, 95975-59-0

11α-hydroxy-16α,17α-epoxyprogesterone

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogen bromide / 5 h / 5 - 10 °C
2: hydrogen; acetic acid / ethanol / 3 h / 40 - 45 °C
3: bromine; hydrogenchloride / ethanol; chloroform / 1 h / 20 - 25 °C
4: N,N-dimethyl-formamide / 0.5 h / 35 - 40 °C
5: manganese(ll) chloride; acetic anhydride; acetic acid / water / 4 h / 5 - 10 °C
View Scheme
11α,17α-dihydroxy-16β-bromo progesterone

11α,17α-dihydroxy-16β-bromo progesterone

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen; acetic acid / ethanol / 3 h / 40 - 45 °C
2: bromine; hydrogenchloride / ethanol; chloroform / 1 h / 20 - 25 °C
3: N,N-dimethyl-formamide / 0.5 h / 35 - 40 °C
4: manganese(ll) chloride; acetic anhydride; acetic acid / water / 4 h / 5 - 10 °C
View Scheme
11α,17α-dihydroxypregn-4-ene-3,20-dione
603-98-5

11α,17α-dihydroxypregn-4-ene-3,20-dione

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: bromine; hydrogenchloride / ethanol; chloroform / 1 h / 20 - 25 °C
2: N,N-dimethyl-formamide / 0.5 h / 35 - 40 °C
3: manganese(ll) chloride; acetic anhydride; acetic acid / water / 4 h / 5 - 10 °C
View Scheme
11α,17α-dihydroxyprogesterone-21-acetate
1250-97-1

11α,17α-dihydroxyprogesterone-21-acetate

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With acetic anhydride; acetic acid; manganese(ll) chloride In water at 5 - 10℃; for 4h;29.1 g
21-acetoxy-9-bromo-17-hydroxy-pregn-4-ene-3,11,20-trione
2206-03-3

21-acetoxy-9-bromo-17-hydroxy-pregn-4-ene-3,11,20-trione

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
With acetic acid; zinc In chloroform at 10 - 15℃; for 10h; Solvent; Inert atmosphere;32.6 g
17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate
1249-67-8

17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate

A

cortexolone 21-acetate
640-87-9

cortexolone 21-acetate

B

Cortisone acetate
50-04-4

Cortisone acetate

Conditions
ConditionsYield
Stage #1: 17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate With potassium carbonate; sodium hydroxide In methanol; chloroform at -5 - 5℃; for 0.333333h; Inert atmosphere;
Stage #2: With acetic acid In methanol; chloroform Inert atmosphere;
Stage #3: With methanol; acetic anhydride; triethylamine In dichloromethane Reagent/catalyst; Solvent; Temperature;
Cortisone acetate
50-04-4

Cortisone acetate

adrenosterone
382-45-6

adrenosterone

Conditions
ConditionsYield
Stage #1: Cortisone acetate With sodium tetrahydroborate In ethanol; dichloromethane for 1.5h; Inert atmosphere;
Stage #2: With sodium periodate In water; acetone at 20℃; for 0.75h; Inert atmosphere;
86%
Product distribution; Rate constant; Irradiation; radiolytic degradation;
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-17α-hydroxypregna-3,5-diene-11,20-dione

21-acetoxy-17α-hydroxypregna-3,5-diene-11,20-dione

Conditions
ConditionsYield
Stage #1: Cortisone acetate With C19H26ClIrN3O(1+)*Cl(1-) In water; acetonitrile at 80℃; for 0.166667h; Green chemistry;
Stage #2: With formic acid In water; acetonitrile at 80℃; for 8h; Green chemistry; regioselective reaction;
81%
Cortisone acetate
50-04-4

Cortisone acetate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

(2R,3aR,3bS,5aS,6R,8aS,8bS)-6-(2-Acetoxy-acetyl)-6-hydroxy-3a,5a-dimethyl-4-oxo-2,3,3a,3b,4,5,5a,6,7,8,8a,8b,9,10-tetradecahydro-dicyclopenta[a,f]naphthalene-2-carboxylic acid methyl ester

(2R,3aR,3bS,5aS,6R,8aS,8bS)-6-(2-Acetoxy-acetyl)-6-hydroxy-3a,5a-dimethyl-4-oxo-2,3,3a,3b,4,5,5a,6,7,8,8a,8b,9,10-tetradecahydro-dicyclopenta[a,f]naphthalene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With thallium(III) nitrate In methanol at 0℃; for 0.5h;66%
Cortisone acetate
50-04-4

Cortisone acetate

Cortisone
53-06-5

Cortisone

Conditions
ConditionsYield
With lipase from Candida cylindracea; octanol In water; acetonitrile at 37℃; for 144h;62%
With potassium hydrogencarbonate
With potassium hydroxide
With sodium methylate
formaldehyd
50-00-0

formaldehyd

Cortisone acetate
50-04-4

Cortisone acetate

17α,20;20,21-bismethylenedioxypregn-4-ene-3,11-dione
3607-68-9

17α,20;20,21-bismethylenedioxypregn-4-ene-3,11-dione

Conditions
ConditionsYield
With hydrogenchloride In chloroform; water at 23℃; for 12h; Inert atmosphere;61%
Cortisone acetate
50-04-4

Cortisone acetate

17α,21-dihydroxy-pregna-4,6-diene-3,11,20-trione 21-acetate
2435-02-1

17α,21-dihydroxy-pregna-4,6-diene-3,11,20-trione 21-acetate

Conditions
ConditionsYield
With chloranil In tert-butyl alcohol for 7h; Heating;60%
With chloranil; xylene
Multi-step reaction with 3 steps
1: N-bromo-succinimide
2: salicylic acid
3: 4-hydroxy-benzaldehyde
View Scheme
Cortisone acetate
50-04-4

Cortisone acetate

20,21-epoxy-17,22-dihydroxy-23,24-dinor-20ξH-chol-4-ene-3,11-dione
115388-24-4

20,21-epoxy-17,22-dihydroxy-23,24-dinor-20ξH-chol-4-ene-3,11-dione

Conditions
ConditionsYield
With methanol; diethyl ether
2-ethyl-2-methyl-1,3-dioxolane
126-39-6

2-ethyl-2-methyl-1,3-dioxolane

Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione
988-16-9

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione

Conditions
ConditionsYield
With toluene-4-sulfonic acid
O-Methylhydroxylamin
67-62-9

O-Methylhydroxylamin

Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3,20-bis-(O-methyl oxime )
125496-85-7

21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3,20-bis-(O-methyl oxime )

2-methallyl-2-methyl-[1,3]dioxolane
4362-28-1

2-methallyl-2-methyl-[1,3]dioxolane

Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione
988-16-9

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione

Conditions
ConditionsYield
With tetrahydrofuran; sulfuric acid
Cortisone acetate
50-04-4

Cortisone acetate

prednisone acetate
125-10-0

prednisone acetate

Conditions
ConditionsYield
With selenium(IV) oxide
With periodic acid
With iodine pentoxide
With Arthrobacter simplex By-2-1317 g
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-4-chloro-17-hydroxy-pregn-4-ene-3,11,20-trione
28444-83-9

21-acetoxy-4-chloro-17-hydroxy-pregn-4-ene-3,11,20-trione

Conditions
ConditionsYield
With hypochloric acid
Multi-step reaction with 2 steps
1: diethyl ether; propionic acid; chlorine
2: pyridine
View Scheme
Multi-step reaction with 2 steps
1: aqueous perchloric acid / Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton und danach mit Acetanhydrid und Pyridin
2: HCl
View Scheme
Cortisone acetate
50-04-4

Cortisone acetate

21,21-dimethoxy-pregn-4-ene-3,11,20-trione
68599-17-7

21,21-dimethoxy-pregn-4-ene-3,11,20-trione

Conditions
ConditionsYield
With hydrogenchloride
Cortisone acetate
50-04-4

Cortisone acetate

A

17-acetoxy-D-homo-androsta-4,16-diene-3,11,17a-trione

17-acetoxy-D-homo-androsta-4,16-diene-3,11,17a-trione

B

17β-acetoxymethyl-17α-hydroxy-D-homo-androst-4-ene-3,11,17a-trione
102084-08-2

17β-acetoxymethyl-17α-hydroxy-D-homo-androst-4-ene-3,11,17a-trione

Conditions
ConditionsYield
With cyclohexanone; aluminum isopropoxide; toluene beim anschliessender Acetylierung;
Cortisone acetate
50-04-4

Cortisone acetate

17β-acetoxymethyl-17α-hydroxy-D-homo-androst-4-ene-3,11,17a-trione
102084-08-2

17β-acetoxymethyl-17α-hydroxy-D-homo-androst-4-ene-3,11,17a-trione

Conditions
ConditionsYield
With cyclohexanone; aluminum isopropoxide; toluene
With cyclohexanone; aluminum isopropoxide In toluene
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-6ξ-bromo-17-hydroxy-pregn-4-ene-3,11,20-trione
426833-73-0

21-acetoxy-6ξ-bromo-17-hydroxy-pregn-4-ene-3,11,20-trione

Conditions
ConditionsYield
With N-Bromosuccinimide
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-4β,5-dichloro-17-hydroxy-5α-pregnane-3,11,20-trione
113862-15-0

21-acetoxy-4β,5-dichloro-17-hydroxy-5α-pregnane-3,11,20-trione

Conditions
ConditionsYield
With diethyl ether; chlorine; propionic acid
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3-oxime
100437-38-5

21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3-oxime

Conditions
ConditionsYield
With hydrogenchloride; hydroxylamine
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3,20-dioxime
124113-30-0

21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3,20-dioxime

Conditions
ConditionsYield
With hydrogenchloride; hydroxylamine
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-17,20βF-dihydroxy-pregn-4-ene-3,11-dione
111615-16-8

21-acetoxy-17,20βF-dihydroxy-pregn-4-ene-3,11-dione

Conditions
ConditionsYield
With sodium tetrahydroborate
Cortisone acetate
50-04-4

Cortisone acetate

A

21-acetoxy-17-hydroxy-5α-pregn-3-ene-11,20-dione
114178-95-9

21-acetoxy-17-hydroxy-5α-pregn-3-ene-11,20-dione

B

21-acetoxy-17-hydroxy-5β-pregn-3-ene-11,20-dione
114178-96-0

21-acetoxy-17-hydroxy-5β-pregn-3-ene-11,20-dione

Conditions
ConditionsYield
With acetic acid; zinc
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-17-hydroxy-5α-pregnane-3,11,20-trione
3751-02-8

21-acetoxy-17-hydroxy-5α-pregnane-3,11,20-trione

Conditions
ConditionsYield
With palladium Hydrogenation;
Cortisone acetate
50-04-4

Cortisone acetate

A

4α,5α-epoxyandrostene-3,11,17-trione
17597-29-4

4α,5α-epoxyandrostene-3,11,17-trione

B

4ξ,5-epoxy-17α-hydroxy-3,11-dioxo-5ξ-androstane-17β-carboxylic acid
102454-93-3

4ξ,5-epoxy-17α-hydroxy-3,11-dioxo-5ξ-androstane-17β-carboxylic acid

Conditions
ConditionsYield
With methanol; sodium hydroxide; dihydrogen peroxide
Cortisone acetate
50-04-4

Cortisone acetate

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione
988-16-9

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione

Conditions
ConditionsYield
With toluene-4-sulfonic acid; ethylene glycol; benzene
With toluene-4-sulfonic acid; ethylene glycol unter vermindertem Druck;

50-04-4Relevant articles and documents

Method for treating prednisone acetate mother liquor

-

Paragraph 0034-0066, (2021/06/02)

The invention relates to the technical field of chemical pharmacy, in particular to a method for treating prednisone acetate mother liquor. The method comprises the following steps: (1) adding a solvent and alkali liquor into the prednisone acetate mother liquor to carry out hydrolysis reaction; (2) after the hydrolysis reaction is finished, adjusting the reaction liquid to be neutral, concentrating under reduced pressure until a large amount of crystals are separated out, and performing suction filtration to obtain a hydrolysate crude product; (3) adding the hydrolysate crude product into a solvent, and refining to obtain a hydrolyzed refined product; (4) adding the hydrolyzed refined substance and a catalyst into a solvent, and reacting with acetic anhydride to obtain a mixture of prednisone acetate and cortisone acetate; and (5) fermenting and dehydrogenating the mixture to obtain the prednisone acetate. According to the treatment method, the prednisone acetate in the prednisone acetate mother liquor can be recycled, particularly, the prednisone acetate in the mother liquor can be recycled, the treatment cost is saved, and the yield of the prednisone acetate is increased; The method can well remove the dehydrogenation RSA and RSA impurities, and is stable in processand simple to operate.

Preparation method of cortisone-21-acetate

-

Paragraph 0038; 0039; 0044-0048; 0053-0057; 0062-0066; 0071, (2020/11/25)

The invention provides a preparation method of cortisone-21-acetate. The preparation method comprises: A) in a protective atmosphere, mixing a compound as shown in a formula I with anhydrous dimethylsulfoxide, a halogenating reagent and a first acid catalyst to carry out an addition-elimination reaction, so as to obtain a compound as shown in a formula III; B) adding the compound shown in the formula III into an organic solvent, and then adding a second acid catalyst and a reducing agent for a reduction reaction to obtain cortisone-21-acetate. The reaction formula is shown in the description.According to the preparation method, a Jones reagent does not need to be adopted, generation of a large amount of chromium-containing wastewater is avoided, the production period is shortened, the production cost is reduced, and clean production is achieved. The purity of the cortisone-21-acetate prepared by the method reaches 99.0% or above, the yield reaches 93% or above, and the preparation method is simple to operate, energy-saving, consumption-reducing, environment-friendly, and particularly suitable for industrial production.

Preparation method of prednisone

-

Paragraph 0012; 0029-0030; 0033-0034; 0037-0038, (2021/03/05)

The invention discloses a preparation method of prednisone, and belongs to the technical field of preparation and processing of medicines. According to the method, hydrocortisone acetate is used as aninitial raw material, and the prednisone is prepared through three steps of oxidation, biological fermentation dehydrogenation and hydrolysis. According to the preparation method of prednisone, the defects of a traditional process are overcome, the target product is high in purity, good in quality stability, high in yield, low in production cost and mild in reaction condition, a highly toxic cyanide reagent is prevented from being used, and the method is easy and convenient to operate, suitable for industrial production and wide in market prospect.

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