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5593-20-4

Basic Information
CAS No.: 5593-20-4
Name: Betamethasone 17,21-dipropionate
Molecular Structure:
Molecular Structure of 5593-20-4 (Betamethasone 17,21-dipropionate)
Formula: C28H37FO7
Molecular Weight: 504.65
Synonyms: Pregna-1,4-diene-3,20-dione,9-fluoro-11b,17,21-trihydroxy-16b-methyl-, 17,21-dipropionate (7CI,8CI);Diproderm;Diprolene;Diprosis;Diprosone;Maxivate;Psorion;Rinderon DP;S3440;Sch 11460;b-Methasone 17,21-dipropionate;Halometasone Monohydrate;Pregna-1,4-diene-3,20-dione,9-fluoro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11b,16b)-;
EINECS: 227-005-2
Density: 1.24 g/cm3
Melting Point: 178 °C
Boiling Point: 603.2 °C at 760 mmHg
Flash Point: 318.6 °C
Solubility:
Appearance: Powder
Hazard Symbols:
Risk Codes:
Safety: 22-24/25
Transport Information:
PSA: 106.97000
LogP: 3.81750
Synthetic route
378-44-9

betamethasone

5593-20-4

betamethasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 2 h / 15 - 20 °C / Inert atmosphere
2: aluminum (III) chloride / 16.5 h / 10 - 30 °C
3: tetrahydrofuran; water / 8 h / 50 - 80 °C / 450.05 Torr
View Scheme
5534-13-4

Betamethasone propionate

5593-20-4

betamethasone dipropionate

Conditions
ConditionsYield
In tetrahydrofuran; water at 50 - 80℃; under 450.045 Torr; for 8h;
5593-20-4

betamethasone dipropionate

65669-64-9

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
With (diethylamido)sulfur trifluoride In dichloromethane for 16h; Ambient temperature;93%
P2 S5

P2 S5

5593-20-4

betamethasone dipropionate

9α-Fluoro-16β-methyl-11,17,21-trihydroxypregna-1,4-dien-20-one-3-thione 17,21-dipropionate

Conditions
ConditionsYield
In toluene60%
5593-20-4

betamethasone dipropionate

72559-81-0

9α-fluoro-6β,11β,17α,21-tetrahydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
With selenious acid In 1,4-dioxane at 100℃; for 72h;44.2%
With selenium(IV) oxide In 1,4-dioxane at 110℃; for 2.5h;25%
Multi-step reaction with 2 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
View Scheme
5593-20-4

betamethasone dipropionate

A

378-44-9

betamethasone

B

5534-13-4

Betamethasone propionate

C

24703-00-2

6β-hydroxybetamethasone

D

78144-00-0

6β-hydroxybetamethasone 17-propionate

Conditions
ConditionsYield
With phosphate buffer; air; plasma of 20 d pregnant Sprague-Dawley rat at 37℃; for 1h; Product distribution; metabolism with tissues (plasma, liver, brain, placenta) from mothers and fetuses of Sprague-Dawley rats sacrificed on day 20 of pregnancy and mice on day 17 of pregnancy, further in vivo;A 14.8 % Chromat.
B 67.8 % Chromat.
C 1.4 % Chromat.
D 2.3 % Chromat.
5593-20-4

betamethasone dipropionate

5534-13-4

Betamethasone propionate

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 6h; Ambient temperature;
5593-20-4

betamethasone dipropionate

98-88-4

benzoyl chloride

82926-64-5

9α-fluoro-3,11β,17α,21-tetrahydroxy-16β-methyl-1,3,5-pregnatriene-20-one 3-benzoate 17,21-dipropionate

Conditions
ConditionsYield
In pyridine at 60℃; for 18h;
5593-20-4

betamethasone dipropionate

A

378-44-9

betamethasone

B

5534-13-4

Betamethasone propionate

C

betamethasone 21-monopropionate

Conditions
ConditionsYield
With sulfuric acid In acetonitrile at 20℃; for 20h; Product distribution; Further Variations:; Temperatures;
5593-20-4

betamethasone dipropionate

A

(Z)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

B

(E)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 20℃; for 0.333333h; Mattox rearrangement;A 30 % Chromat.
B 10 % Chromat.
With sodium hydroxide In water; acetonitrile at 20℃; for 0.333333h; Mattox rearrangement;
5593-20-4

betamethasone dipropionate

72559-88-7

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,6,20-trione 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
View Scheme
5593-20-4

betamethasone dipropionate

72559-27-4

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-acetate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 51 percent / pyridine / 5 h / Ambient temperature
View Scheme
5593-20-4

betamethasone dipropionate

72559-99-0

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-isobutyrate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 63 percent / pyridine / 5 h / Ambient temperature
View Scheme
5593-20-4

betamethasone dipropionate

72560-00-0

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-valerate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 58 percent / pyridine / 5 h / Ambient temperature
View Scheme
5593-20-4

betamethasone dipropionate

72559-32-1

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-trimethylacetate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 56 percent / various solvent(s) / 5 h / Ambient temperature
View Scheme
5593-20-4

betamethasone dipropionate

72559-98-9

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-benzoate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 70 percent / pyridine / 5 h / Ambient temperature
View Scheme
5593-20-4

betamethasone dipropionate

82934-60-9

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-methanesulfonate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 41 percent / pyridine / 5 h / Ambient temperature
View Scheme
5593-20-4

betamethasone dipropionate

127034-59-7

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
View Scheme
5593-20-4

betamethasone dipropionate

127034-60-0

16β-methyl-12β,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
3: 57 percent / 48percent aq. HF / 1.5 h / 22 °C
View Scheme
5593-20-4

betamethasone dipropionate

127034-61-1

16β-methyl-12α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
3: 19 percent / 48percent aq. HF / 1.5 h / 22 °C
View Scheme
p-TSA hydrate

p-TSA hydrate

5593-20-4

betamethasone dipropionate

80226-13-7

9α-Fluoro-11β,17α,21-trihydroxy-16β-methyl-5β-pregnane-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
palladium In dichloromethane; 4,4-dichlorobutan-2-one; acetone
palladium In dichloromethane; 4,4-dichlorobutan-2-one; acetone
5593-20-4

betamethasone dipropionate

64681-07-8

9α-Fluoro-16β-methyl-11,17-21-trihydroxypregna-1,4-dien-20-one-3-thione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: sodium hydroxide; acetic acid / methanol
View Scheme
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Chemistry


IUPAC Name: [2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-Fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
Molecular Weight: 504.587583 [g/mol]
Molecular Formula: C28H37FO7
XLogP3: 3.6
H-Bond Donor: 1
H-Bond Acceptor: 8 
EINECS: 227-005-2
Product Categories: Biochemistry; Hydroxyketosteroids; Steroids 
refractive index: 69 °(C=1, Dioxane)
Water Solubility: 0.724 mg/L at 25 °C
Index of Refraction: 1.549
Molar Refractivity: 128.66 cm3
Molar Volume: 403.9 cm3
Surface Tension: 49.1 dyne/cm
Density: 1.24 g/cm3
Flash Point: 318.6 °C
Enthalpy of Vaporization: 102.93 kJ/mol
Boiling Point: 603.2 °C at 760 mmHg
Vapour Pressure: 4.58E-17 mmHg at 25 °C
Melting Point: 178 °C
Classification Code of Betamethasone dipropionate (CAS NO.5593-20-4): Anti-Inflammatory Agents; Drug / Therapeutic Agent; Glucocorticoid; Hormone; Reproductive Effect 

Uses

 Betamethasone dipropionate (CAS NO.5593-20-4) is applied as a topical cream, ointment, lotion or gel (Diprolene) to treat itching and other minor skin conditions such as eczema.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 103mg/kg (103mg/kg)   Drugs in Japan Vol. 6, Pg. 753, 1982.
mouse LD50 oral > 5gm/kg (5000mg/kg) BEHAVIORAL: ANTIPSYCHOTIC

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
mouse LD50 subcutaneous 78100ug/kg (78.1mg/kg)   Drugs in Japan Vol. 6, Pg. 753, 1982.
rat LD50 intraperitoneal > 4gm/kg (4000mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
rat LD50 oral > 4gm/kg (4000mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
rat LD50 subcutaneous > 4gm/kg (4000mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.

Safety Profile

Safety Statements: 22-24/25
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
WGK Germany: 2
RTECS: TU4058000
Poison by subcutaneous and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of F.

Specification

  Betamethasone dipropionate (CAS NO.5593-20-4), its Synonyms are 9-Fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate ; Alphatrex ; Betamethasone 17,21-dipropionate ; Diproderm ; Diprolene ; Diprolene AF ; Diprosis ; Diprosone ; Maxivate ; Psorion ; Rinderon DP ; beta-Methasone 17,21-dipropionate ; Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-16-beta-methyl-, 17,21-dipropionate ; Pregna-1,4-diene-3,20-dione, 9-fluoro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11beta,16beta) .