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638-94-8

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638-94-8 Usage

Chemical Properties

Off-White Solid

Originator

Tridesilon,Dome,US,1972

Uses

Different sources of media describe the Uses of 638-94-8 differently. You can refer to the following data:
1. antifungal
2. Anti-inflammatory. Desonide has also been found as an impurity in budesonide (B689490).
3. Desonide(Budesonide EP Impurity F) is an impurity of Budesonide (B689490), an anti-inflammatory.

Definition

ChEBI: Triamcinolone acetonide with hydrogen instead of the fluorine substituent at position 9. A corticosteroid anti-inflammatory, it is used topically as a cream, ointment or lotion for the treatment of various skin disorders.

Indications

Desonide (DesOwen, Tridesilon) is a synthetic corticosteroid.

Manufacturing Process

Preparation of 11β,21-Dihydroxy-16α,17α-Isopropylidenedioxy-1,4- Pregnadiene-3,20-Dione: A solution of 11β,16α,17α,21-tetrahydroxy-1,4- pregnadiene-3,20-dione (40 mg) in acetone (10 ml) containing hydrochloric acid (three drops; d 1.19) is boiled 3n the steam bath for two minutes and then allowed to stand for eighteen hours at room temperature. The reaction mixture is diluted with water (50 ml) and extracted with chloroform (3x25 ml), the combined extracts then being washed with water (30 ml) and dried over anhydrous sodium sulfate. The residue obtained by removal of solvent crystallized from ethyl acetate-petroleum ether as small plates (25 mg), melting point 257°-260°C.

Brand name

Desowen (Galderma); Tridesilon (Perrigo).

Therapeutic Function

Antiinflammatory

Check Digit Verification of cas no

The CAS Registry Mumber 638-94-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 8 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 638-94:
(5*6)+(4*3)+(3*8)+(2*9)+(1*4)=88
88 % 10 = 8
So 638-94-8 is a valid CAS Registry Number.
InChI:InChI=1/C24H32O6/c1-21(2)29-19-10-16-15-6-5-13-9-14(26)7-8-22(13,3)20(15)17(27)11-23(16,4)24(19,30-21)18(28)12-25/h7-9,15-17,19-20,25,27H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,20+,22-,23-,24+/m0/s1

638-94-8 Well-known Company Product Price

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  • USP

  • (1173304)  Desonide  United States Pharmacopeia (USP) Reference Standard

  • 638-94-8

  • 1173304-250MG

  • 15,467.40CNY

  • Detail

638-94-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name desonide

1.2 Other means of identification

Product number -
Other names 16a-Hydroxyprednisolone Acetonide

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:638-94-8 SDS

638-94-8Synthetic route

desonide
13951-70-7

desonide

acetone

acetone

Conditions
ConditionsYield
With boron trifluoride In tetrahydrofuran; acetonitrile at -5 - 10℃; Inert atmosphere;85%
With methanesulfonic acid at -10℃; for 0.133333h; Temperature;
C26H32O7

C26H32O7

desonide
638-94-8

desonide

Conditions
ConditionsYield
With sodium hydroxide In methanol at 30℃; for 0.666667h; Temperature; Inert atmosphere; Large scale;81%
desonide
13951-70-7

desonide

desonide
638-94-8

desonide

Conditions
ConditionsYield
With perchloric acid; acetone
11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide 21-acetate
25092-25-5

11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide 21-acetate

desonide
638-94-8

desonide

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane at -5 - 5℃; for 2h; Inert atmosphere;8.60 g
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

desonide
638-94-8

desonide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: formic acid; potassium permanganate / acetone; water / 0.5 h / -7 - -3 °C / Industrial scale
2: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; perchloric acid / water; tetrahydrofuran / 1 h / -8 - -4 °C / Industrial scale
3: chromium(III) chloride hexahydrate; zinc; mercaptoacetic acid / N,N-dimethyl-formamide; dimethyl sulfoxide / 1 h / -10 °C / Inert atmosphere; Industrial scale
4: perchloric acid / 1.5 h / 26 - 35 °C / Inert atmosphere
5: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 5 °C / Inert atmosphere
View Scheme
16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate
77017-20-0

16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate

desonide
638-94-8

desonide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; perchloric acid / water; tetrahydrofuran / 1 h / -8 - -4 °C / Industrial scale
2: chromium(III) chloride hexahydrate; zinc; mercaptoacetic acid / N,N-dimethyl-formamide; dimethyl sulfoxide / 1 h / -10 °C / Inert atmosphere; Industrial scale
3: perchloric acid / 1.5 h / 26 - 35 °C / Inert atmosphere
4: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 5 °C / Inert atmosphere
View Scheme
9α-bromo-11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate
91160-89-3

9α-bromo-11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate

desonide
638-94-8

desonide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: chromium(III) chloride hexahydrate; zinc; mercaptoacetic acid / N,N-dimethyl-formamide; dimethyl sulfoxide / 1 h / -10 °C / Inert atmosphere; Industrial scale
2: perchloric acid / 1.5 h / 26 - 35 °C / Inert atmosphere
3: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 5 °C / Inert atmosphere
View Scheme
11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate
86401-80-1

11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate

desonide
638-94-8

desonide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: perchloric acid / 1.5 h / 26 - 35 °C / Inert atmosphere
2: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 5 °C / Inert atmosphere
View Scheme
2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

desonide
638-94-8

desonide

desonide 21-isobutyrate
78806-61-8

desonide 21-isobutyrate

Conditions
ConditionsYield
With potassium carbonate In acetone for 1.5h; ethanol;99.7%
With potassium carbonate In acetone Reflux;
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

desonide
638-94-8

desonide

11β-hydroxy-16α,17α-isopropylidenedioxy-21-mesyloxy-1,4-pregnadiene-3,20-dione
5541-39-9

11β-hydroxy-16α,17α-isopropylidenedioxy-21-mesyloxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
With pyridine at 0℃;99%
butyraldehyde

butyraldehyde

desonide
638-94-8

desonide

budesonide
51372-29-3

budesonide

Conditions
ConditionsYield
With phosphoric acid at 0 - 5℃; for 21.5h; Product distribution / selectivity;98.6%
desonide
638-94-8

desonide

A

11β-hydroxy-16α,17α-<(1-methylethylidene)bis(oxy)>-3-oxoandrosta-1,4-diene

11β-hydroxy-16α,17α-<(1-methylethylidene)bis(oxy)>-3-oxoandrosta-1,4-diene

B

11β-hydroxy-16α,17α-<(1-methylethylidene)bis(oxy)>-3-oxoandrosta-1,4-diene-17β-carboxylic acid

11β-hydroxy-16α,17α-<(1-methylethylidene)bis(oxy)>-3-oxoandrosta-1,4-diene-17β-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide; dihydrogen peroxide In methanol for 2h; ambient temperature;A 7.5%
B 88%
acetic anhydride
108-24-7

acetic anhydride

desonide
638-94-8

desonide

desonide diacetate

desonide diacetate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;82%
desonide
638-94-8

desonide

11β,21-dihydroxy-16α,17α-(1-methylethylidenedioxy)-1,5-cyclopregn-3-ene-2,20-dione

11β,21-dihydroxy-16α,17α-(1-methylethylidenedioxy)-1,5-cyclopregn-3-ene-2,20-dione

Conditions
ConditionsYield
With oxygen In acetonitrile for 2.5h; UV-irradiation;67%
methylsulfanyl-acetic acid
2444-37-3

methylsulfanyl-acetic acid

desonide
638-94-8

desonide

11β-Hydroxy-16α,17α-isopropylidenedioxy-21-(methylthio)acetoxy-1,4-pregnadiene-3,20-dione
121507-18-4

11β-Hydroxy-16α,17α-isopropylidenedioxy-21-(methylthio)acetoxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 4h; Heating;64%
desonide
638-94-8

desonide

A

17β-hydroperoxy-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-diene-3-one

17β-hydroperoxy-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-diene-3-one

B

11β,21-dihydroxy-16α,17α-(1-methylethylidenedioxy)-1,5-cyclopregn-3-ene-2,20-dione

11β,21-dihydroxy-16α,17α-(1-methylethylidenedioxy)-1,5-cyclopregn-3-ene-2,20-dione

Conditions
ConditionsYield
With oxygen In acetonitrile for 2.5h; UV-irradiation;A 52%
B 26%
desonide
638-94-8

desonide

11β-hydroxy-16α,17α-<(1-methylethylidene)bis(oxy)>-3-oxoandrosta-1,4-diene

11β-hydroxy-16α,17α-<(1-methylethylidene)bis(oxy)>-3-oxoandrosta-1,4-diene

Conditions
ConditionsYield
In acetonitrile for 2h; UV-irradiation;50%
4-pentenal
2100-17-6

4-pentenal

desonide
638-94-8

desonide

C26H34O6

C26H34O6

Conditions
ConditionsYield
With perchloric acid at 20℃;33%
desonide
638-94-8

desonide

tert butyl 4-formylpiperidine-1-carboxylate
137076-22-3

tert butyl 4-formylpiperidine-1-carboxylate

(1S,2S,4R,6R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-(piperidin-4-yl)-5,7-dioxapentacyclo[10.8.0.02'9.04'8.013'18]icosa-14,17-dien-16-one

(1S,2S,4R,6R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-(piperidin-4-yl)-5,7-dioxapentacyclo[10.8.0.02'9.04'8.013'18]icosa-14,17-dien-16-one

Conditions
ConditionsYield
With perchloric acid In water at 0 - 20℃;13%
desonide
638-94-8

desonide

11β,16α-dihydroxyandrosta-1,4-diene-3,17-dione

11β,16α-dihydroxyandrosta-1,4-diene-3,17-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / oxygen / acetonitrile / 2.5 h / UV-irradiation
2: 15 mg / triphenylphosphine / CH2Cl2 / 2 h
View Scheme
desonide
638-94-8

desonide

11β-hydroxy-16α,17α-isopropylidenedioxy-21-mercapto-1,4-pregnadiene-3,20-dione
119137-96-1

11β-hydroxy-16α,17α-isopropylidenedioxy-21-mercapto-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / pyridine / 0 °C
2: 1) acetone, 30 min, 2) acetone, 6 h, reflux
3: 85 percent / hydrazine hydrate / tetrahydrofuran / 0.25 h / -10 - -5 °C
View Scheme
desonide
638-94-8

desonide

11-β-hydroxy-16α,17α-isopropylidenedioxy-21-methylthio-1,4-pregnadiene-3,20-dione
119138-00-0

11-β-hydroxy-16α,17α-isopropylidenedioxy-21-methylthio-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / pyridine / 0 °C
2: 1) acetone, 30 min, 2) acetone, 6 h, reflux
3: 85 percent / hydrazine hydrate / tetrahydrofuran / 0.25 h / -10 - -5 °C
4: 78 percent / Et3N / dimethylformamide
View Scheme
desonide
638-94-8

desonide

11-β-hydroxy-16α,17α-isopropylidenedioxy-21-ethylthio-1,4-pregnadiene-3,20-dione
119138-01-1

11-β-hydroxy-16α,17α-isopropylidenedioxy-21-ethylthio-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / pyridine / 0 °C
2: 1) acetone, 30 min, 2) acetone, 6 h, reflux
3: 85 percent / hydrazine hydrate / tetrahydrofuran / 0.25 h / -10 - -5 °C
4: 39 percent / Et3N / dimethylformamide
View Scheme
desonide
638-94-8

desonide

21-acetylthio-11β-hydroxy-16α,17α-isopropylidenedioxy-1,4-pregnadiene-3,20-dione
119137-93-8

21-acetylthio-11β-hydroxy-16α,17α-isopropylidenedioxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / pyridine / 0 °C
2: 1) acetone, 30 min, 2) acetone, 6 h, reflux
View Scheme
desonide
638-94-8

desonide

11-β-hydroxy-16α,17α-isopropylidenedioxy-21-methoxycarbonylthio-1,4-pregnadiene-3,20-dione
119138-02-2

11-β-hydroxy-16α,17α-isopropylidenedioxy-21-methoxycarbonylthio-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / pyridine / 0 °C
2: 1) acetone, 30 min, 2) acetone, 6 h, reflux
3: 85 percent / hydrazine hydrate / tetrahydrofuran / 0.25 h / -10 - -5 °C
4: 1) EtN(iPr)2 / 1) CH2Cl2, 0 deg C, 10 min, 2) CH2Cl2, 0 deg C, 30 min
View Scheme
desonide
638-94-8

desonide

11-β-hydroxy-16α,17α-isopropylidenedioxy-21-ethoxycarbonylthio-1,4-pregnadiene-3,20-dione
119138-03-3

11-β-hydroxy-16α,17α-isopropylidenedioxy-21-ethoxycarbonylthio-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / pyridine / 0 °C
2: 1) acetone, 30 min, 2) acetone, 6 h, reflux
3: 85 percent / hydrazine hydrate / tetrahydrofuran / 0.25 h / -10 - -5 °C
4: 1) EtN(iPr)2 / 1) CH2Cl2, 0 deg C, 10 min, 2) CH2Cl2, 0 deg C, 30 min
View Scheme
N-methyl-piperidine-4-carboxaldehyde
50675-21-3

N-methyl-piperidine-4-carboxaldehyde

desonide
638-94-8

desonide

A

16-α-hydroxyprednisolone-16,17-αβ-acetal of N-methyl-4-formylpiperidine

16-α-hydroxyprednisolone-16,17-αβ-acetal of N-methyl-4-formylpiperidine

B

C28H39NO6

C28H39NO6

Conditions
ConditionsYield
With perchloric acid In water; 1-Nitropropane at 20℃; for 48h;
desonide
638-94-8

desonide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

desisobutyryl ciclesonide
161115-59-9

desisobutyryl ciclesonide

Conditions
ConditionsYield
With perchloric acid In water; 1-Nitropropane at 0 - 20℃;59 %Chromat.
desonide
638-94-8

desonide

C27H36O8S

C27H36O8S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: perchloric acid / 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
View Scheme
desonide
638-94-8

desonide

C36H42N2O5S

C36H42N2O5S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: perchloric acid / 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
3: potassium carbonate / acetone / Reflux
View Scheme
desonide
638-94-8

desonide

A

C34H38N2O5S

C34H38N2O5S

B

C34H38N2O5S

C34H38N2O5S

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: perchloric acid / 20 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
3: potassium carbonate / acetone / Reflux
4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 70 °C
View Scheme
glutaric anhydride,
108-55-4

glutaric anhydride,

desonide
638-94-8

desonide

triamcinolone acetonoide-21-glutarate

triamcinolone acetonoide-21-glutarate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl acetamide; N,N-dimethyl-formamide for 24h;
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: methanesulfonic acid / 1 h / 65 - 80 °C
1.2: 12 h / -5 - 15 °C
2.1: sodium hydroxide / methanol; dichloromethane / -10 - 0 °C / Inert atmosphere
View Scheme

638-94-8Relevant articles and documents

-

Bernstein et al.

, p. 4573 (1959)

-

A synthesis method of budesonide (by machine translation)

-

Paragraph 0030; 0032; 0038; 0046; 0054, (2018/07/30)

The invention discloses a budesonide synthetic method, under the protection of inert gas, under the catalysis of the 1st catalyst, sulfur dioxide will prednisone acetate eliminated reaction, then under the catalysis of the 2nd catalyst, through the oxidizing agent after the elimination of the products of the oxidation reaction, then under the catalysis of the 3rd catalyst, after oxidation through the acetone to products of the condensation process, the condensation product of the 4th under catalysis of the catalyst for selective reduction, finally 5th after reduction of the product of the hydrolysis catalyst under the catalysis of the reaction Desonide; the invention relates to a synthesis method of budesonide to prednisone acetate as raw materials through eliminating, oxidation, condensation, reduction, hydrolysis can be budesonide, synthesis process all the solvent in the process of all the recycled, and the reaction process in the absence of a heavy metal involved in the reaction, the technological process is mild, low energy consumption, is a green clean synthesis method. (by machine translation)

NOVEL PROCESS FOR PREPARATION OF GLUCOCORTICOID STEROIDS

-

, (2016/08/23)

The present invention discloses a process for the preparation of 16, 17-acetals of pregnane derivatives having formula (I) wherein each substituent is independently selected from; R1 is H or CH3; R2 is C1-C6 linear or branched alkyl, alkynyl group or cycloalkyl group; aryl or heteroaryl group; or R1 and R2 combine to form saturated, unsaturated C3-C6 cyclic or heterocyclic ring; R3 and R4 are same or different and each independently represents H or halogen; R5 is -OH or –OCOR wherein R represents H or C1-C6 linear, branched or cyclic alkyl group that may be substituted.

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