17-cyano-9,17-dihydroxyandrost -4-ene-3-one (cas 116256-35-0)
17-cyano-9,17-dihydroxyandrost -4-ene-3-one
17-Cyano-9,17-dihydroxyandrost-4-ene-3-one Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | 17β-Cyano-9α,17α-dihydroxyandrost-4-ene-3-one |
| CAS Number | 116256-35-0 |
| Synonyms | 17β-Cyano-9α,17α-dihydroxyandrost-4-ene-3-one, Androst-4-ene-17-carbonitrile, 9α,17α-dihydroxy-3-oxo-, (17α)- |
| Chemical Formula | C₂₀H₂₇NO₃ |
| Molecular Weight | 329.43 |
| EINECS Number | 601-418-1 |
| Melting Point | 229–230°C |
| Boiling Point | 537.1°C (calculated) |
| Density | 1.24 g/cm³ (calculated) |
| Storage Conditions | Sealed in dry, stored at 2–8°C |
| Solubility | Sparingly soluble in chloroform and ethyl acetate; slightly soluble in methanol; water solubility 1.01 mg/L (20°C) |
| Appearance | Off-white to pale yellow solid |
| Optical Activity | [α]²⁵/D +190° ±5° (c = 1 in chloroform) |
| Applications | Pharmaceutical Intermediate: Key precursor for synthesizing glucocorticoids and antiandrogenic drugs. Research Use: Steroid metabolism studies and antineoplastic drug development. |
| 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 9α and 17α hydroxyl groups to androst-4-ene-3,17-dione via microbial or chemical methods. 2. Cyanation: Conversion of the 17α-hydroxyl group to a cyano group using trimethylsilyl cyanide or cyanation reagents. |
| Safety Information | Hazard Codes: Xi (Irritant) Risk Statements: R36/37/38 (Irritating to eyes, respiratory system, skin) Precautionary Measures: S22 (Avoid inhalation of dust), S24/25 (Avoid contact with skin and eyes) |
| MSDS | Material Safety Data Sheet available from suppliers |
Supplementary Notes
- Structural Features:
- Contains a 17β-cyano group and 9α,17α-dihydroxyl groups on an androstane skeleton. The cyano group enhances metabolic stability, making it a critical precursor for potent glucocorticoids (e.g., dexamethasone derivatives).
- Stereochemistry at C9α and C17α is crucial for receptor binding affinity.
- Synthesis Challenges:
- Requires precise stereochemical control during hydroxylation to avoid epimerization at C9 or C17.
- Hydroxyl protection strategies (e.g., acetylation) are often employed to enable selective cyanation.
- Applications in Medicine:
- Anti-inflammatory: Investigated for treating inflammatory disorders or as antiandrogenic agents (e.g., prostate cancer).
- Agricultural Potential: Studied as a plant growth regulator.
- Regulatory Status:
- Compliant with EP and USP standards; special permits may be required in certain countries.
For detailed toxicological data or formulation protocols, consult specialized pharmacological references (e.g., PubChem, ChemSpider).
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