11β,17α-dihydroxy-6α-methylpregna-1,4-diene-3,20-dione (cas 6870-94-6)
11β,17α-Dihydroxy-6α-methylpregna-1,4-diene-3,20-dione (6870-94-6) Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | (6α,11β)-11,17-Dihydroxy-6-methylpregna-1,4-diene-3,20-dione |
| CAS Number | 6870-94-6 |
| Synonyms | NSC 125051, Fluorometholone Impurity 1, Methylprednisolone EP Impurity L, Cortisol-17β acid |
| Chemical Formula | C₂₂H₃₀O₄ |
| Molecular Weight | 358.47 |
| EINECS Number | 614-710-9 |
| Melting Point | 222–231°C |
| Boiling Point | 530.3 ± 50.0°C (predicted) |
| Density | 1.21 ± 0.1 g/cm³ (predicted) |
| pKa | 12.86 ± 0.70 (predicted) |
| Appearance | White to pale beige solid |
| Solubility | Slightly soluble in chloroform, DMSO, and methanol (sonicated) |
| Optical Activity | [α]²⁵/D +190° ±5° (c = 1 in chloroform) |
| Applications | Pharmaceutical Intermediate: Critical impurity in fluorometholone synthesis; used for quality control in corticosteroid formulations. 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: Compliant with EP/USP standards (≤0.1% for key impurities). |
| Synthesis Pathway | 1. Hydroxylation: Introduction of 11β- and 17α-hydroxyl groups via microbial or chemical methods. 2. Methylation: C6α-methylation using methylating agents (e.g., methyl iodide). |
| Safety Information | Hazard Codes: Xi (Irritant), N (Dangerous for the environment) Risk Statements: R36/37/38 (irritating to eyes, respiratory system, skin); R51/53 (toxic to aquatic life). Precautionary Measures: S22 (Avoid inhalation), S24/25 (Avoid contact), S61 (Avoid release to environment). |
| MSDS | Available from suppliers |
Supplementary Notes
- Structural Features:
- Contains a 6α-methyl group and 11β,17α-dihydroxyl groups on a pregnadiene backbone. The 6α-methylation enhances metabolic stability, making it a key intermediate in corticosteroid synthesis.
- Stereochemistry (6α,11β,17α) is critical for binding affinity to glucocorticoid receptors.
- Synthesis Challenges:
- Requires selective methylation at C6 without affecting hydroxyl groups at C11 and C17.
- Epimerization control at C11 during hydroxylation is essential for pharmaceutical-grade purity.
- Applications in Medicine:
- Anti-inflammatory: Acts as an impurity reference standard for fluorometholone, a synthetic corticosteroid used in ophthalmic formulations (e.g., for treating ocular inflammation).
- Toxicity Studies: Investigated for environmental impact due to its potential aquatic toxicity.
- Regulatory Status:
- Compliant with EP and USP 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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