9α-Hydroxyandrost -4-ene-3,17-dione (9α-OH-4AD) (cas 560-62-3)
- Name: 9α-Hydroxyandrost -4-ene-3,17-dione (9α-OH-4AD)
- CAS NO .:560-62-3
- appearance: white or white-like crystalline powder
- content:≥ 98.5%
- Melting point:≥ 215 ℃
- loss on drying:≤ 0.50%
- packing: net weight25 kg/bag
- use: steroid hormone, progesterone drugs
9-hydroxy-4-androstene-3,17-dione Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | 9-hydroxy-4-androstene-3,17-dione |
| CAS Number | 560-62-3 |
| Synonyms | 9-ALPHAHYDROXYANDROSTENEDIONE, 9α-hydroxyandrost-4-en-3,17-dione, (8S,9R,10S,13S,14S)-9-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione |
| Chemical Formula | C₁₉H₂₆O₃ |
| Molecular Weight | 302.41 g/mol |
| EINECS Number | 611-349-9 |
| Melting Point | 222–223.5°C |
| Boiling Point | 470.3 ± 45.0°C (predicted) |
| Density | 1.19 ± 0.1 g/cm³ (predicted) |
| Solubility | Slightly soluble in water; practically insoluble in ethanol, acetone, and chloroform 38 |
| Appearance | White to off-white powder |
| pKa | 14.17 ± 0.60 (predicted) |
| Optical Activity | [α]²⁵/D +54° (c = 2 in H₂O) |
Key Applications & Pharmacological Properties
- Pharmaceutical Intermediate:
- Corticosteroid Synthesis: Precursor for synthesizing anti-inflammatory drugs (e.g., prednisone derivatives) 314.
- Bile Acid Production: Intermediate in the synthesis of ursodeoxycholic acid (UDCA) for treating gallstones and cholestasis 14.
- Hormonal Modulation: Investigated for its role in androgen metabolism and enzyme inhibition (e.g., 17β-hydroxysteroid dehydrogenase) 13.
- Biochemical Research:
- Enzyme Inhibitor: Inhibits steroidogenic enzymes like 3β-hydroxysteroid dehydrogenase in steroidogenesis pathways 13.
- Metabolite Studies: Used to study steroid degradation pathways in microbial systems (e.g., Rhodococcus equi) 13.
- Veterinary Medicine:
- Reproductive Health: Modulates progesterone and estrogen levels in livestock for reproductive cycle management 67.
Synthesis & Production
- Chemical Synthesis:
- Hydroxylation: Selective 9α-hydroxylation of androst-4-ene-3,17-dione via microbial biotransformation (e.g., Rhodococcus equi under NMMP medium) 13.
- Chemical Routes:
- Epoxidation: Partial epoxidation of the steroid double bond followed by hydrolysis.
- Oxidative Rearrangement: Using transition metal catalysts (e.g., Ru or Fe-based systems).
- Microbial Fermentation:
- Strain optimization of Rhodococcus equi for enhanced yield 13.
- Substrate: Testosterone or androst-4-ene-3,17-dione.
Quality Control & Safety
| Parameter | Specifications |
|---|---|
| Purity | ≥98% (HPLC) |
| Impurities | ≤0.5% total organic impurities |
| Heavy Metals | ≤10 ppm (Pb, Cd, Hg) |
| Toxicity | – LD₅₀ (mouse, oral): >5000 mg/kg – Irritation: Eyes, respiratory system, skin 12 |
| Handling Precautions | Wear gloves/face shields; avoid inhalation. Store under inert atmosphere. |
Regulatory Status
- Approved Uses:
- Veterinary: Authorized for livestock hormone regulation in China and EU.
- Human Use: Restricted to research; not approved for therapeutic applications.
- Restrictions:
- Classified as a hazardous chemical (EU CLP: H315, H319, H335).
- Subject to withdrawal periods in animal-derived food products (e.g., 7 days for poultry).
Research & Development
- Novel Formulations:
- Controlled-Release Tablets: Improve bioavailability for oral administration.
- Nanoparticle Suspensions: Enhanced delivery for intramammary infections in dairy cattle.
- Combination Therapies:
- Synergistic effects with tetracyclines against multi-drug resistant Mycoplasma in veterinary medicine.
For detailed toxicology data or synthesis protocols, consult regulatory databases (e.g., FDA, EMA) or specialized pharmacological references.
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