11α-Hydroxyandrost-4-ene-317-dione (cas 564-33-0)
11α-Hydroxyandrost-4-ene-317-dione
11β-Hydroxyandrost-4-ene-3,17-dione Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | 11β-Hydroxyandrost-4-ene-3,17-dione |
| CAS Number | 564-33-0 |
| Synonyms | 11-Hydroxyandrostenedione, 11α-Hydroxyandrostenedione, 4-Androsten-11α-ol-3,17-dione, NSC 7423 |
| Chemical Formula | C₁₉H₂₆O₃ |
| Molecular Weight | 302.41 |
| EINECS Number | 1312995-182-4 |
| Melting Point | 226–227°C (lit.) |
| Boiling Point | 475.3 ± 45.0°C (predicted) |
| Density | 1.19 ± 0.1 g/cm³ (predicted) |
| Solubility | Slightly soluble in chloroform and methanol |
| Appearance | Light yellow to orange solid |
| Optical Activity | [α]²⁵/D +190° ±5° (c = 1 in chloroform) |
| pKa | 14.49 ± 0.60 (predicted) |
| Applications | Pharmaceutical Use: Key intermediate in synthesizing formebolone (anabolic steroid). Research Use: Androgen receptor studies and steroid metabolism investigations. |
| Hazard Classification | Not explicitly listed; handle with standard chemical safety precautions. |
| Synthesis Pathway | 1. Hydroxylation: Selective hydroxylation at C11β position of androst-4-ene-3,17-dione. 2. Purification: Recrystallization from ethanol/water mixtures. |
| Quality Control | – HPLC: C18 column, methanol-water (60:40) mobile phase, UV detection at 240 nm. – Impurity Limits: Total impurities ≤0.5%. |
| Stability | 24 months (protected from light, dry, stored at 2–8°C) |
| Key Suppliers | Sigma-Aldrich, Wuhan Dongkangyuan Biotech, Hebei Hongtan Biotechnology |
| 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 an 11β-hydroxyl group and a 3,17-dione backbone, making it a critical precursor for anabolic steroids like formebolone.
- The 11β-hydroxy group enhances androgenic activity and metabolic stability.
- Synthesis Challenges:
- Requires precise stereochemical control during hydroxylation to avoid epimerization at C11.
- Solvent selection (e.g., ethanol/water) is critical for effective crystallization.
- Applications in Research:
- Models for studying androgen receptor binding and steroidogenesis pathways.
- Investigated for potential use in hormone replacement therapies and metabolic disease studies.
For detailed toxicological data or formulation protocols, consult specialized pharmacological references.
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