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Desonide

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Name

Desonide

EINECS 211-351-6
CAS No. 638-94-8 Density 1.3 g/cm3
PSA 93.06000 LogP 2.32670
Solubility N/A Melting Point 274 - 275oC
Formula C24H32O6 Boiling Point 580.1 °C at 760 mmHg
Molecular Weight 416.514 Flash Point 196.9 °C
Transport Information N/A Appearance Powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 638-94-8 (Desonide) Hazard Symbols N/A
Synonyms

Prenacid;Desilux;Pregna-1,4-diene-3,20-dione,11,21- dihydroxy-16,17-[(1-methylethylidene)bis- (oxy)]-,(11a,16R)-;Topifug;Locapred;Tridesilon;Flusemidon;Hamiltoderm;Desonide [USAN:BAN:INN];Pregna-1,4-diene-3,20-dione, 11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11beta,16alpha)-;Apolar;Otic Tridesilon;Steroderm;Prednisolone-16,17-acetonide, 16-alpha-hydroxy-;DesOwen;Tridesonit;Sterax;Desonidum [INN-Latin];Budesonide acetonide;

 

Desonide Synthetic route

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

638-94-8

desonide

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

desonide

638-94-8

desonide

Conditions
ConditionsYield
With perchloric acid; acetone
25092-25-5

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

638-94-8

desonide

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

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
77017-20-0

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

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
91160-89-3

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

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
86401-80-1

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

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
97-72-3

2-Methylpropionic anhydride

638-94-8

desonide

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;
124-63-0

methanesulfonyl chloride

638-94-8

desonide

5541-39-9

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

Conditions
ConditionsYield
With pyridine at 0℃;99%

Desonide Specification

1. Introduction of Desonide

Desonide is one kind of white needle crystal. This chemical belongs to the Product Categories which include Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. Desonide is mainly used to treat atopic dermatitis ,seborrheic dermatitis, and contact dermatitis in both adults and children , it is available as a cream, ointment, lotio.

2. Properties of Desonide

Desonide has the following prperty datas: (1)Freely Rotating Bonds: 4; (2)Polar Surface Area: 71.06?2; (3)Index of Refraction: 1.598; (4)Molar Refractivity: 109.26 cm3; (5)Molar Volume: 320.1 cm3; (6)Surface Tension: 55.9 dyne/cm; (7)Density: 1.3 g/cm3; (8)Flash Point: 196.9 °C; (9)Enthalpy of Vaporization: 99.64 kJ/mol; (10)Boiling Point: 580.1 °C at 760 mmHg; (11)Vapour Pressure: 7.16E-16 mmHg at 25°C.

3. Structure Descriptors of Desonide

You could convert the following datas into the molecular structure:
(1).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
(2).Smiles:O1C(C)(C)O[C@@H]2C[C@@H]3[C@@](C[C@@H](O)[C@H]4[C@@H]3CCC=3[C@@]4(C=CC(C3)=O)C)(C)[C@]12C(=O)CO

4. Toxicity of Desonide

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 3710mg/kg (3710mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 111, 1970.
 
rat LD50 subcutaneous 93mg/kg (93mg/kg)   Toxicology and Applied Pharmacology. Vol. 20, Pg. 522, 1971.
 

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