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| | (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Basic information |
| Product Name: | (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid | | Synonyms: | impurity J;6a,9a-Difluoro-11b,17a-dihydroxy-16a-methylpregna- 3-oxo-1,4-diene-17b-carboxylic Acid;Fluticasone 17b-Carboxylic Acid;6A,9A-DIFLUORO-11SS,17A-DIHYDROXY-3-OXOANDROSTA-1,4-DIENE-17SS-CARBOXYLIC ACID;ANDROSTA-1,4-DIENE-17-CARBOXYLIC ACID,6,9-DIFLUORO-11,17- DIHYDROXY-16-METHYL-3-OXO-,(6ALPHA,11BETA,16ALPHA,17ALPHA)-;ANDROSTA-1,4-DIENE-17-CARBOXYLIC ACID,6,9-DIFLUORO-11,17- DIHYDROXY-16-METHYL-3-OXO-,(6A,11SS,16A,17A)-;(6a,11,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carboxylic Acid;6a,9a-Difluoro-11,17a-dihydroxy-16a-methylpregna-3-oxo-1,4-diene-17-carboxylic Acid | | CAS: | 28416-82-2 | | MF: | C21H26F2O5 | | MW: | 396.42 | | EINECS: | 206-597-6 | | Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;28416-82-2 | | Mol File: | 28416-82-2.mol |  |
| | (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Chemical Properties |
| Melting point | 303-305°C | | Boiling point | 568.4±50.0 °C(Predicted) | | density | 1.38±0.1 g/cm3(Predicted) | | storage temp. | Refrigerator | | solubility | Acetone (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly) | | pka | 3.49±0.70(Predicted) | | form | Solid | | color | White to Off-White | | Major Application | pharmaceutical (small molecule) | | InChIKey | QSVBUQTYFQFEHC-TXKOFOEMNA-N | | SMILES | [C@]12(C)C=CC(=O)C=C1[C@@H](F)C[C@@]1([H])[C@]3([H])C[C@@H](C)[C@](O)(C(O)=O)[C@@]3(C)C[C@H](O)[C@]21F |&1:0,8,11,13,16,18,23,26,28,r| |
| WGK Germany | WGK 3 | | HS Code | 2937220000 | | Storage Class | 11 - Combustible Solids |
| | (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Usage And Synthesis |
| Description | Fluticasone 17β-carboxylic acid is an intermediate in the synthesis of the glucocorticosteroid fluticasone propionate . | | Chemical Properties | White Solid | | Uses | The major metabolite of Fluticasone. Anti-inflammatory agent. | | Uses | Fluticasone intermediate. Anti-inflammatory agent | | General Description |
Fluticasone 17β-carboxylic acid ((6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid) is a compound of interest in studying structure-activity relationships within corticosteroid analogs. In research, this compound is examined for its potential interactions with glucocorticoid receptors, given its structural similarity to fluticasone, which is known for its affinity to these receptors. The 17β-carboxylic acid moiety may alter the compound's binding characteristics. In biochemistry, fluticasone 17β-carboxylic acid is used to probe the metabolic pathways of fluticasone, as it may be a metabolite or intermediate.
| | Synthesis |
To a suspension of flumethasone (1.19 g, 2.9 mmol) in tetrahydrofuran (11 ml) was added a solution of periodic acid (2.25 g, 9.9 mmol) in water (5.3 ml). The resulting solution was stirred at RT for 1 h. The tetrahydrofuran was removed in vacuo to leave an aqueous suspension which was filtered, and the solid washed with water and dried to give 1.17 g (100%) of the (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid (Fluticasone 17β-Carboxylic Acid) as a colorless solid.
| | References | [1] JIADI ZHOU Weike S Can Jin. Improved Synthesis of Fluticasone Propionate[J]. Organic Process Research & Development, 2014, 18 8: 928-933. DOI: 10.1021/op5001226 |
| | (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid Preparation Products And Raw materials |
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