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Dexamethasone-17-acetate

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Dexamethasone-17-acetate Basic information
Product Name:Dexamethasone-17-acetate
Synonyms:20-dione,9-fluoro-11-beta,17,21-trihydroxy-16-alpha-methyl-pregna-4-diene-3;9alpha-Fluoro-16alpha-methylprednisolone acetate;9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione21-acetate;9-Fluoro-11,17-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-21-yl acetate;9-fluoro-11-beta,17,21-trihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione;9-Fluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate;9-Fluoro-11-beta,17,21-trihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione acetate;Dalalone D.P.
CAS:1177-87-3
MF:C24H31FO6
MW:434.5
EINECS:214-646-8
Product Categories:Hormone Drugs;DECADRON;Intermediates & Fine Chemicals;Pharmaceuticals;Pharmaceutical intermediate;API;Biochemistry;Hydroxyketosteroids;Steroids
Mol File:1177-87-3.mol
Dexamethasone-17-acetate Structure
Dexamethasone-17-acetate Chemical Properties
Melting point 238-240 °C(lit.)
alpha D25 +73° (chloroform) (Arth, 1958); D +77.6° (Oliveto)
Boiling point 579.4±50.0 °C(Predicted)
density 1.1517 (estimate)
refractive index 87 ° (C=1, Dioxane)
storage temp. 2-8°C
solubility Soluble at 100 mg/ml in acetone
form Powder
pka12.08±0.70(Predicted)
color White
Water Solubility 13mg/L(25 ºC)
Merck 2943
BRN 2342608
CAS DataBase Reference1177-87-3(CAS DataBase Reference)
NIST Chemistry ReferencePrednisolone, 9alpha-fluoro-16alpha-methyl-, acetate(1177-87-3)
EPA Substance Registry SystemDexamethasone-21-acetate (1177-87-3)
Safety Information
Hazard Codes Xi
Risk Statements 43
Safety Statements 36/37
WGK Germany 3
RTECS TU4050000
TSCA Yes
HS Code 29372290
MSDS Information
ProviderLanguage
SigmaAldrich English
Dexamethasone-17-acetate Usage And Synthesis
Chemical PropertiesOff-White Solid
OriginatorDexacen,Central,US,1977
UsesProtected Dexamethasone, a glucocorticoid anti-inflammatory agent.
Manufacturing ProcessThe preparation of dexamethasone acetate is described in US Patent 3,007,923 as follows. 1.5 cc of dimethylformamide and 1.5 cc of anhydrous hydrofluoric acid are admixed and treated with 480 mg of 9β,11β-epoxy-17αhydroxy-21-acetoxy-16α-methyl-?1,4-pregnadiene-3,20-dione (prepared according to E.P. Oliveto et al, J. Am. Chem. Soc., 80, 44331, 1958). The steroid dissolves in about 15 minutes. The reaction mixture is shaken for two hours at a temperature between 0 and +5°C, and then poured into 75 cc of
water containing in suspension, 7.5 grams of sodium bicarbonate. The mixture is vacuum filtered, the filter cake washed and then dried at 100°C, yielding 460 mg of crude hexadecadrol contaminated with a small amount of the starting material. A single recrystallization from methylene chloride yields 370 mg of the pure product having a melting point of 170°C and 229°C. The mother liquor yields 62 mg of the starting material, and a remainder constituting a mixture of starting and final materials with little other contamination.
Brand nameDecadron (Merck).
Therapeutic Function9-Fluoro-11β,17-dihydroxy-21-acetoxy-16α-methylpregna1,4-diene-3,20-dione
Safety ProfileExperimental teratogenic and reproductive effects. A steroid. When heated to decomposition it emits toxic fumes of F-.
Purification MethodsDexamethasone 21-acetate is purified on neutral Al2O3 using CHCl3 as eluent, the fractions are evaporated, and the residue is recrystallised from CHCl3. It has max at 239nm. [Oliveto et al. J Am Chem Soc 8 0 4431 1958]. [Beilstein 8 IV 3501.]
Tag:Dexamethasone-17-acetate(1177-87-3) Related Product Information
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