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Alclometasone-17,21-dipropionate

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Name

Alclometasone-17,21-dipropionate

EINECS 266-464-3
CAS No. 66734-13-2 Density 1.26 g/cm3
PSA 106.97000 LogP 3.94270
Solubility N/A Melting Point 212-216°
Formula C28H37ClO7 Boiling Point 636 °C at 760 mmHg
Molecular Weight 521.051 Flash Point 338.4 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 66734-13-2 (Alclometasone-17,21-dipropionate) Hazard Symbols N/A
Synonyms

Aclovate;Alclometasone dipropionate;Almeta;Delonal;Sch 22219;Vaderm;

Article Data 5

Alclometasone-17,21-dipropionate Synthetic route

16α-methyl-7,11-dihydroxy-17α,21-bispropionyloxypregna-4-ene-1,4-diene-3,20-dione

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
With pyridine; phosphorus trichloride In toluene at 40 - 45℃; Solvent; Reagent/catalyst; Green chemistry;64.2%
With pyridine; phosphorus trichloride In toluene at 40 - 45℃; Solvent; Reagent/catalyst;64.2 g

(7α,11β,16α)-7-hydroxy-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dione

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
With pyridine; phosphorus trichloride In toluene at 40 - 45℃; Solvent; Reagent/catalyst;64.2%
67212-74-2

16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 17,21-dipropionate

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 16h; Ambient temperature;15%
13209-52-4

16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 21-acetate

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 21 percent / HCl, DDQ / dioxane / 24 h / Ambient temperature
2: 53 percent / sat. aq. NaHCO3 / methanol / 2 h / Ambient temperature
3: TsOH*H2O / dimethylsulfoxide / 2 h / Ambient temperature
4: 1.) aq. AcOH, 2.) pyridine / 1.) RT, 1 h, 2.) RT, 3.5 h
5: 15 percent / HCl / dioxane / 16 h / Ambient temperature
View Scheme
13954-10-4

16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: TsOH*H2O / dimethylsulfoxide / 2 h / Ambient temperature
2: 1.) aq. AcOH, 2.) pyridine / 1.) RT, 1 h, 2.) RT, 3.5 h
3: 15 percent / HCl / dioxane / 16 h / Ambient temperature
View Scheme
13796-64-0

16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 21-acetate

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 53 percent / sat. aq. NaHCO3 / methanol / 2 h / Ambient temperature
2: TsOH*H2O / dimethylsulfoxide / 2 h / Ambient temperature
3: 1.) aq. AcOH, 2.) pyridine / 1.) RT, 1 h, 2.) RT, 3.5 h
4: 15 percent / HCl / dioxane / 16 h / Ambient temperature
View Scheme
67212-72-0

16α-methyl-11β,17α,21-trihydroxy-1,4,6-pregnatriene-3,20-dione 17α,21-ethylorthopropionate

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) aq. AcOH, 2.) pyridine / 1.) RT, 1 h, 2.) RT, 3.5 h
2: 15 percent / HCl / dioxane / 16 h / Ambient temperature
View Scheme

3-ethylene ether-16α-methyl-17α,21-bispropionyloxy-pregnane-3,5-diene-7,11,20-trione

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol / 25 - 30 °C / Green chemistry
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C / Green chemistry
3: pyridine; phosphorus trichloride / toluene / 40 - 45 °C / Green chemistry
View Scheme
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / methanol / 25 - 30 °C
1.2: 25 - 30 °C / pH 2 - 3
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C
3.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate; methanol / 25 - 30 °C
1.2: 25 - 30 °C / pH 2 - 3
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C
3.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C
View Scheme

16α-methyl hydrocortisone

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: toluene-4-sulfonic acid / 20 - 25 °C / Green chemistry
2: acetic acid; chromium(VI) oxide / chloroform; water / 20 - 25 °C / Green chemistry
3: toluene-4-sulfonic acid / 30 - 35 °C / Green chemistry
4: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C / Green chemistry
5: sodium tetrahydroborate / methanol / 25 - 30 °C / Green chemistry
6: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C / Green chemistry
7: pyridine; phosphorus trichloride / toluene / 40 - 45 °C / Green chemistry
View Scheme
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / propionic acid / 20 - 25 °C
2.1: chromium(VI) oxide; water / chloroform / 20 - 25 °C
3.1: toluene-4-sulfonic acid / propionic acid / 30 - 35 °C
4.1: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C
5.1: sodium tetrahydroborate / methanol / 25 - 30 °C
5.2: 25 - 30 °C / pH 2 - 3
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C
7.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C
View Scheme
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / 20 - 25 °C
2.1: acetic acid; chromium(VI) oxide / water / 20 - 25 °C
3.1: toluene-4-sulfonic acid / 30 - 35 °C
4.1: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C
5.1: sodium tetrahydroborate; methanol / 25 - 30 °C
5.2: 25 - 30 °C / pH 2 - 3
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C
7.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C
View Scheme

16α-methylhydrocortison-21-yl propionate

66734-13-2

alclometasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: acetic acid; chromium(VI) oxide / chloroform; water / 20 - 25 °C / Green chemistry
2: toluene-4-sulfonic acid / 30 - 35 °C / Green chemistry
3: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C / Green chemistry
4: sodium tetrahydroborate / methanol / 25 - 30 °C / Green chemistry
5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C / Green chemistry
6: pyridine; phosphorus trichloride / toluene / 40 - 45 °C / Green chemistry
View Scheme
Multi-step reaction with 6 steps
1.1: chromium(VI) oxide; water / chloroform / 20 - 25 °C
2.1: toluene-4-sulfonic acid / propionic acid / 30 - 35 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C
4.1: sodium tetrahydroborate / methanol / 25 - 30 °C
4.2: 25 - 30 °C / pH 2 - 3
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C
6.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C
View Scheme
Multi-step reaction with 6 steps
1.1: acetic acid; chromium(VI) oxide / water / 20 - 25 °C
2.1: toluene-4-sulfonic acid / 30 - 35 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 20 - 25 °C
4.1: sodium tetrahydroborate; methanol / 25 - 30 °C
4.2: 25 - 30 °C / pH 2 - 3
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 75 - 80 °C
6.1: pyridine; phosphorus trichloride / toluene / 40 - 45 °C
View Scheme

Alclometasone-17,21-dipropionate Chemical Properties

Molecular Formula: C28H37ClO7
Molar mass: 521.04 g/mol
EINECS: 266-464-3
Density: 1.26 g/cm3
Flash Point: 338.4 °C
Index of Refraction: 1.562
Boiling Point: 636 °C at 760 mmHg
Vapour Pressure: 7.55E-19 mmHg at 25°C
Structure of Alclometasone-17,21-dipropionate (66734-13-2):

XLogP3-AA: 3.2
H-Bond Donor: 1
H-Bond Acceptor: 7
Systematic Name: [(7R,8S,9S,10R,11S,13S,14S,16R,17R)-7-Chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] propanoate 
SMILES: O=C(OCC(=O)[C@@]1(OC(=O)CC)[C@@H](C[C@H]2[C@H]4[C@H]([C@@H](O)C[C@]12C)[C@]/3(/C=C\C(=O)\C=C\3C[C@H]4Cl)C)C)CC 
InChI: InChI=1/C28H37ClO7/c1-6-22(33)35-14-21(32)28(36-23(34)7-2)15(3)10-18-24-19(29)12-16-11-17(30)8-9-26(16,4)25(24)20(31)13-27(18,28)5/h8-9,11,15,18-20,24-25,31H,6-7,10,12-14H2,1-5H3/t15-,18+,19-,20+,24-,25+,26+,27+,28+/m1/s1 
InChIKey: DJHCCTTVDRAMEH-DUUJBDRPBB 
Std. InChI: InChI=1S/C28H37ClO7/c1-6-22(33)35-14-21(32)28(36-23(34)7-2)15(3)10-18-24-19(29)12-16-11-17(30)8-9-26(16,4)25(24)20(31)13-27(18,28)5/h8-9,11,15,18-20,24-25,31H,6-7,10,12-14H2,1-5H3/t15-,18+,19-,20+,24-,25+,26+,27+,28+/m1/s1 
Std. InChIKey: DJHCCTTVDRAMEH-DUUJBDRPSA-N

Alclometasone-17,21-dipropionate Uses

Alclometasone-17,21-dipropionate(66734-13-2) is used of topical cortical steroid hormone, and has potent local anti-inflammatory, anti-itch and shrinking blood vessels.It has been used for eczema, atopic dermatitis, psoriasis and other skin diseases.

Alclometasone-17,21-dipropionate Production

Under the action of 2,3 - Dichloro-5,6 - dicyano-benzoquinone (DDQ) to give one H2O to get compound (Ⅱ) .With Sodium bicarbonate for ester hydrolysis of 21, and then has the original acid Triethyl reaction, the 17-bit and 21-OH to form a ring of the original ester (Ⅳ).Then, with C anhydride to have the reaction to get Double-propionate (Ⅵ). Final with Hydrogen chloride for addition to get: Alclometasone-17,21-dipropionate(66734-13-2). The total yield was 2.678 percent.

Alclometasone-17,21-dipropionate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 15mg/kg (15mg/kg)   Drugs in Japan Vol. -, Pg. 70, 1990.
dog LD50 skin > 15mg/kg (15mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 735, 1988.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. -, Pg. 70, 1990.
mouse LD50 subcutaneous 2506mg/kg (2506mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1253, 1987.
rat LD50 oral 3593mg/kg (3593mg/kg)   Drugs in Japan Vol. -, Pg. 70, 1990.
rat LD50 skin > 75mg/kg (75mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 735, 1988.
rat LD50 subcutaneous 3593mg/kg (3593mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 1253, 1987.

Alclometasone-17,21-dipropionate Safety Profile

Moderately toxic by subcutaneous route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of HCl.

Alclometasone-17,21-dipropionate Specification

 Alclometasone-17,21-dipropionate (66734-13-2) also can be called Delonal ; Aclosone ; Modrasone ; Aclovate ; 7alpha-Chloro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate and (7R,8S,9S,10R,11S,13S,14S,16R,17R)-7-Chlor-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[(propanoyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-ylpropanoat .

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