11α-Hydroxyandrost-4-ene-317-dione (cas 564-33-0)
11β-Hydroxyandrost-4-ene-3,17-dione (564-33-0) Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | (11β)-11-Hydroxyandrosta-1,4-dien-3,17-dione |
| CAS Number | 564-33-0 |
| Synonyms | 11-Hydroxyandrost-4-ene-3,17-dione; 11α-Hydroxyandrost-4-ene-3,17-dione; Androst-4-ene-3,17-dione,11-hydroxy-, (11β)- |
| Chemical Formula | C₁₉H₂₆O₃ |
| Molecular Weight | 302.41 |
| EINECS Number | 1312995-182-4 |
| Melting Point | 226–227°C |
| Boiling Point | 475.3 ± 45.0°C (predicted) |
| Density | 1.19 ± 0.1 g/cm³ (predicted) |
| Solubility | Sparingly soluble in chloroform and methanol (sonicated) |
| Appearance | Light yellow to orange solid |
| pKa | 14.49 ± 0.60 (predicted) |
| Optical Activity | [α]²⁵/D +190° ±5° (c = 1 in chloroform) |
| Applications | Diagnostic Marker: Distinguishes adrenal vs. ovarian origin of hyperandrogenism in clinical diagnostics59. Pharmaceutical Intermediate: Precursor for synthesizing corticosteroids and androgenic agents. Research Use: Investigating steroidogenesis disorders (e.g., congenital adrenal hyperplasia). |
| Quality Control | – HPLC: C18 column, methanol-water (60:40) mobile phase, UV detection at 240 nm. – Impurity Limits: ≤0.5% total impurities. |
| Synthesis Pathway | 1. Hydroxylation: Enzymatic introduction of 11β-hydroxyl group via adrenal-derived enzymes (e.g., CYP11B1) or chemical methods. 2. Crystallization: Purification from steroid-rich extracts. |
| 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 11β-hydroxyl group on an androstane skeleton. The β-configuration at C11 is critical for its role as a diagnostic marker in adrenal disorders59.
- Stereochemistry (11β,17α) influences receptor-binding affinity in steroidogenic pathways.
- Clinical Significance:
- Adrenal Hyperandrogenism: Elevated plasma levels indicate adrenal-derived androgen excess (e.g., Cushing’s syndrome)5.
- Congenital Adrenal Hyperplasia (CAH): Low 11β-hydroxyandrostenedione correlates with 21-hydroxylase deficiency9.
- Synthesis Challenges:
- Requires enzymatic or regioselective hydroxylation to avoid over-oxidation of the 3-keto group.
- Purification challenges due to similar polarity with other androstane metabolites.
- Regulatory Status:
- Classified as a pharmaceutical intermediate under GMP guidelines.
- Compliant with USP and EP standards for steroid purity.
For detailed toxicological data or diagnostic protocols, consult specialized pharmacological references (e.g., PubChem, ChemSpider).
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