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66734-13-2

Basic Information
CAS No.: 66734-13-2
Name: Alclometasone-17,21-dipropionate
Article Data: 5
Molecular Structure:
Molecular Structure of 66734-13-2 (Alclometasone-17,21-dipropionate)
Formula: C28H37ClO7
Molecular Weight: 521.051
Synonyms: Aclovate;Alclometasone dipropionate;Almeta;Delonal;Sch 22219;Vaderm;
EINECS: 266-464-3
Density: 1.26 g/cm3
Melting Point: 212-216°
Boiling Point: 636 °C at 760 mmHg
Flash Point: 338.4 °C
PSA: 106.97000
LogP: 3.94270
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
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Chemistry

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

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.

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.

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.

Safety Profile

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

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 .