11β,21-dihydroxypregna -1,4,16-triene-3,20-dione 21- acetate (cas 3044-42-6)
11β,21-dihydroxypregna -1,4,16-triene-3,20-dione 21- acetate
11β,21-Dihydroxypregna-1,4,16-Triene-3,20-Dione 21-Acetate Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | (11β)-21-(Acetyloxy)-11-hydroxypregna-1,4,16-triene-3,20-dione |
| CAS Number | 3044-42-6 |
| Synonyms | Budesonide Impurity 3, Budesonide 1,4,16-Triene Impurity, 21-Acetoxy-11β-hydroxypregna-1,4,16-triene-3,20-dione |
| Chemical Formula | C₂₃H₂₈O₅ |
| Molecular Weight | 384.47 |
| EINECS Number | 221-250-9 |
| Melting Point | 208–209°C |
| Boiling Point | 553.4 ± 50.0°C (predicted) |
| Density | 1.24 ± 0.1 g/cm³ (predicted) |
| Solubility | Sparingly soluble in DCM and ethyl acetate |
| Appearance | Brown solid |
| pKa | 14.30 ± 0.70 (predicted) |
| Optical Activity | [α]²⁵/D +190° ±5° (c = 1 in chloroform) |
| Applications | Pharmaceutical Intermediate: Critical precursor for synthesizing corticosteroids (e.g., budesonide). Research Use: Steroid metabolism studies and impurity profiling. |
| Quality Control | – HPLC: C18 column, methanol-water (60:40) mobile phase, UV detection at 240 nm. – Impurity Limits: Total impurities ≤0.5%. |
| Synthesis Pathway | 1. Hydroxylation: Introduction of 11β- and 17α-hydroxyl groups via microbial or chemical methods. 2. Acetylation: 21-hydroxyl group acetylated using acetic anhydride. |
| Safety Information | Risk Statements: R36/37/38 (irritating to eyes, respiratory system, skin) Precautionary Measures: S22 (Avoid inhalation), S24/25 (Avoid contact) |
| MSDS | Available from suppliers |
Supplementary Notes
- Structural Features:
- Contains a 17α-hydroxyl group and 21-acetate ester on a pregnatriene backbone. The 11β-hydroxyl group is critical for glucocorticoid receptor binding.
- Stereochemistry (11β,17α) ensures biological activity in corticosteroid synthesis.
- Synthesis Challenges:
- Requires selective acetylation of the 21-hydroxyl group without affecting other hydroxyl sites.
- Epimerization control at C11 and C17 during hydroxylation is essential for pharmaceutical-grade purity.
- Applications in Medicine:
- Anti-inflammatory: Intermediate for budesonide, a synthetic corticosteroid used in asthma and Crohn’s disease.
- Impurity Reference: Acts as a reference standard for purity testing of corticosteroid formulations.
- Regulatory Status:
- Compliant with USP and EP standards; regulated under pharmaceutical GMP guidelines.
For detailed toxicological data or formulation protocols, consult specialized pharmacological references (e.g., PubChem, ChemSpider).
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