17alpha-Hydroxy-17β-cyanoandrost-4-en-3-on (cas 77881-13-1 )
17alpha-Hydroxy-17β-cyanoandrost-4-en-3-on
(17α)-17-Hydroxy-3-oxoandrost-4-ene-17-carbonitrile Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | (17α)-17-Hydroxy-3-oxoandrost-4-ene-17-carbonitrile |
| CAS Number | 77881-13-1 |
| Synonyms | Cyanohydrin matter, Androstenedione cyanohydrin, 17β-cyano-17α-hydroxyandrost-4-en-3-one |
| Chemical Formula | C₂₀H₂₇NO₂ |
| Molecular Weight | 313.43 |
| EINECS Number | 278-780-9 |
| Melting Point | 222–226°C |
| Boiling Point | 498.5 ± 45.0°C (predicted) |
| Density | 1.17 ± 0.1 g/cm³ (predicted) |
| Vapor Pressure | 0.001 Pa at 25°C |
| pKa | 11.20 ± 0.60 (predicted) |
| Water Solubility | 10 mg/L at 25°C |
| Appearance | White to off-white solid |
| Optical Activity | [α]²⁵/D +190° ±5° (c = 1 in chloroform) |
| Applications | Pharmaceutical Intermediate: Key precursor for synthesizing glucocorticoids and antiandrogenic agents. Research Use: Steroid metabolism studies and antineoplastic drug development. |
| Hazard Classification | Non-flammable |
| Storage Conditions | Sealed in dry, stored at 2–8°C |
| 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 17β-cyano group on an androstane skeleton. The cyano group enhances metabolic stability, making it critical for synthesizing potent glucocorticoids.
- Stereochemistry at C17 (α-hydroxyl and β-cyano) is essential for receptor binding affinity.
- Synthesis Challenges:
- Requires stereoselective hydroxylation and cyanation to avoid epimerization at C17.
- Cyanation steps may involve toxic reagents (e.g., cyanogen bromide), necessitating stringent safety protocols.
- Applications in Medicine:
- Anti-inflammatory: Investigated for treating inflammatory disorders or as antiandrogenic agents (e.g., prostate cancer).
- Hormonal Therapy: Potential use in hormone replacement therapies or metabolic disease management.
- Regulatory Status:
- Compliant with EP and USP standards; may require permits for specialized applications.
For detailed toxicological data or formulation protocols, consult specialized pharmacological references (e.g., PubChem, ChemSpider).
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