(5α,10α,17β)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)- estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal (cas 84371-57-3)
Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | (5α,10α,17β)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal |
| CAS Number | 84371-57-3 |
| Synonyms | 5α,10α-Epoxy-3,3-(ethylenedioxy)-17β-hydroxy-17α-(1-propynyl)-9(11)-estrene; CYMI-001 |
| Chemical Formula | C₂₃H₃₀O₄ |
| Molecular Weight | 370.48 |
| EINECS Number | Not explicitly listed in search results |
| Melting Point | 122–125°C |
| Boiling Point | Predicted ~533.5°C (based on similar steroids) |
| Density | 1.30 ± 0.1 g/cm³ (predicted) |
| Solubility | Sparingly soluble in chloroform and methanol (sonicated) |
| Appearance | White to pale yellow solid |
| pKa | Not explicitly reported; estimated ~12–13 (based on ketone and ether functionalities) |
| Optical Activity | [α]²⁵/D +71° ±5° (c = 1 in chloroform) |
| Applications | Pharmaceutical Intermediate: Critical precursor for synthesizing Mifepristone derivatives (antiprogestin drugs). Research Use: Progesterone receptor antagonist studies. |
| 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. Epoxidation: Selective epoxidation of estr-9(11)-ene using peracids. 2. Propynyl Introduction: Grignard reaction with propynyl magnesium bromide at C17. 3. Cyclization: Formation of 1,2-ethanediyl acetal via acid-catalyzed cyclization. |
| Key Suppliers | – Wuhan Dingxintong Pharmaceutical (Tel: 027-59207796, China) – Jingmen Dongxin Biotech (Tel: 13047189721, China) – Shenzhen Juhe Biochemical (Tel: +86-400-002-6226, China) |
| Safety Information | Risk Statements: H301 (Toxic if swallowed), H331 (Toxic if inhaled). Precautionary Measures: S22 (Avoid inhalation), S24/25 (Avoid contact), S61 (Avoid release to environment). |
| MSDS | Available from suppliers |
Supplementary Notes
- Structural Features:
- Contains a 5,10-epoxy group and 17α-propynyl substituent on an estrane skeleton. The epoxy structure enhances molecular rigidity, while the propynyl group serves as a reactive site for subsequent coupling reactions.
- Stereochemistry (5α,10α,17β) is critical for receptor selectivity, influencing its activity as a progesterone receptor antagonist.
- Synthesis Challenges:
- Requires precise control of epoxidation and propynyl introduction sequences to avoid side reactions (e.g., double bond isomerization).
- Acetal cyclization must be optimized under acidic conditions to prevent hydrolysis or polymerization.
- Applications in Medicine:
- Antiprogestin Development: Key intermediate for synthesizing Mifepristone analogs, used in emergency contraception or Cushing’s syndrome treatment.
- Biochemical Research: Tools for studying progesterone receptor signaling pathways.
- Regulatory Status:
- Classified as a pharmaceutical intermediate under GMP guidelines.
- Subject to controlled substance regulations due to its potential use in synthetic opioid production.
For detailed toxicological data or formulation protocols, consult specialized pharmacological references (e.g., PubChem, ChemSpider).
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