Introduction：Basic information about Dexamethasone-17-acetate CAS 1177-87-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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;API;Intermediates & Fine Chemicals;Pharmaceuticals;Pharmaceutical intermediate;Biochemistry;Hydroxyketosteroids;Steroids;1177-87-3 |
| Mol File: | 1177-87-3.mol |
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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) |
| vapor pressure | <0.0000001 kPa ( 25 °C) |
| refractive index | 87 ° (C=1, Dioxane) |
| storage temp. | 2-8°C |
| solubility | Soluble at 100 mg/ml in acetone |
| pka | 12.08±0.70(Predicted) |
| form | Powder |
| color | White |
| biological source | synthetic |
| Water Solubility | 13mg/L(25 ºC) |
| Merck | 2943 |
| BRN | 2342608 |
| Major Application | pharmaceutical (small molecule) |
| InChIKey | AKUJBENLRBOFTD-RPRRAYFGSA-N |
| SMILES | [H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1(F)[C@@H](O)C[C@@]4(C)[C@@]2([H])C[C@@H](C)[C@]4(O)C(=O)COC(C)=O |
| CAS DataBase Reference | 1177-87-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Prednisolone, 9alpha-fluoro-16alpha-methyl-, acetate(1177-87-3) |
| EPA Substance Registry System | Dexamethasone-21-acetate (1177-87-3) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 43 |
| Safety Statements | 36/37 |
| WGK Germany | 3 |
| RTECS | TU4050000 |
| TSCA | TSCA listed |
| HS Code | 29372290 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Repr. 1B |
Dexamethasone-17-acetate Usage And Synthesis
| Chemical Properties | Off-White Solid |
| Originator | Dexacen,Central,US,1977 |
| Uses | Dexamethasone has many uses in the treatment of cancer. Dexamethasone relieves inflammation in various parts of the body. To treat or prevent allergic reactions. As treatment of certain kinds of autoimmune diseases, skin conditions, asthma and other lung conditions. As treatment for a variety of cancers, such as leukemia, lymphoma, and multiple myeloma. It is also used for replacement therapy in adrenal insufficiency and in a screening test for the diagnosis of cushing's syndrome. Dexamethasone Acetate has also been determined to markedly decrease the number of activated macrophages. In addition, Dexamethasone Acetate has been observed to significantly decrease mRNA levels of TPH2 (tryptophan hydroxylase-2) in the raphe nuclei of C57/Bl6 mice. |
| Uses | Dexamethasone acetate is used as a pharmaceutical primary standard to quantify the analyte in pharmaceutical formulations using chromatography ttechniques. |
| Uses | Protected Dexamethasone, a glucocorticoid anti-inflammatory agent. |
| Definition | ChEBI: Dexamethasone acetate is a corticosteroid hormone. |
| Manufacturing Process | The preparation of dexamethasone acetate is described in US Patent3,007,923 as follows. 1.5 cc of dimethylformamide and 1.5 cc of anhydroushydrofluoric acid are admixed and treated with 480 mg of 9β,11β-epoxy-17αhydroxy-21-acetoxy-16α-methyl-?1,4-pregnadiene-3,20-dione (preparedaccording to E.P. Oliveto et al, J. Am. Chem. Soc., 80, 44331, 1958). Thesteroid dissolves in about 15 minutes. The reaction mixture is shaken for twohours 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 mixtureis vacuum filtered, the filter cake washed and then dried at 100°C, yielding460 mg of crude hexadecadrol contaminated with a small amount of thestarting material. A single recrystallization from methylene chloride yields 370mg of the pure product having a melting point of 170°C and 229°C. Themother liquor yields 62 mg of the starting material, and a remainderconstituting a mixture of starting and final materials with little othercontamination. |
| Brand name | Decadron (Merck). |
| Therapeutic Function | 9-Fluoro-11β,17-dihydroxy-21-acetoxy-16α-methylpregna1,4-diene-3,20-dione |
| Safety Profile | Experimental teratogenic and reproductive effects. A steroid. When heated to decomposition it emits toxic fumes of F-. |
| Purification Methods | Dexamethasone 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.] |
Dexamethasone-17-acetate Preparation Products And Raw materials
| Raw materials | Hydrogen fluoride-->Ethylene glycol-->Methyl bromide-->Progesterone-->11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione |
| Preparation Products | 9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione21-phosphate piperazine salt-->Dexamethasone |
