17α-Hydroxyprogesterone (cas 604-09-1)
- CAS NO .:604-09-1
- appearance: white or white-like crystalline powder
- content:≥ 98.0%
- Melting point:≥ 208 ℃
- loss on drying:≤ 0.50%
- packing: net weight20 kg/bag
- use: steroid hormone, progesterone drugs
Hydroxyprogesterone (68-96-2) Comprehensive Information Table
| Category | Details |
|---|---|
| Chemical Name | 17α-Hydroxypregn-4-en-3,20-dione |
| CAS Number | 68-96-2 |
| Synonyms | 17-Hydroxyprogesterone, 4-Pregnen-17α-ol-3,20-dione, Gestagenogador, Prodox |
| Chemical Formula | C₂₁H₃₀O₃ |
| Molecular Weight | 330.46 g/mol |
| EINECS Number | 200-699-4 |
| Melting Point | 276°C |
| Boiling Point | 407.89°C (estimated) |
| Density | 1.0998 g/cm³ (estimated) |
| Solubility | Slightly soluble in chloroform; practically insoluble in water |
| Appearance | White to off-white crystalline powder |
| pKa | 13.03 ± 0.60 (predicted) |
| Optical Activity | [α]²⁵/D +54° (c = 2 in CHCl₃) |
Key Applications & Pharmacological Properties
- Pharmaceutical Uses:
- Pregnancy Support: Used to prevent preterm labor in high-risk pregnancies (e.g., prior preterm birth history) 16.
- Preeclampsia Management: Improves clinical symptoms in rat models by regulating vascular tone and inflammation 2.
- Hormonal Therapy: Acts as a progesterone receptor agonist to stabilize the endometrium and suppress ovulation.
- Biochemical Role:
- Precursor in Steroidogenesis: Intermediate in cortisol and androstenedione biosynthesis.
- Receptor Modulation: Binds to progesterone receptors (PR) with lower affinity than progesterone but exhibits partial glucocorticoid receptor (GR) antagonism 7.
- Veterinary Medicine:
- Reproductive Health: Used in livestock to manage estrous cycles and prevent miscarriages.
Synthesis & Production
- Chemical Synthesis:
- Hydroxylation: Selective 17α-hydroxylation of pregnenolone via microbial biotransformation (e.g., Rhodococcus equi) or chemical oxidation 23.
- Key Steps:
- Epoxidation: Formation of an epoxide intermediate at C5–C6.
- Hydrolysis & Reduction: Converts epoxide to diol, followed by selective oxidation at C17.
- Biological Production:
- Derived from cholesterol via pregnenolone in adrenal glands or ovaries.
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 – Reproductive Toxicity: Risk of fetal virilization |
| Handling Precautions | Wear gloves/face shields; avoid inhalation. Store at 2–8°C in airtight containers. |
Regulatory Status
- Approved Uses:
- Veterinary: Authorized for livestock in the EU and China.
- Human Use: Restricted to research; not approved for therapeutic applications in many countries.
- 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: Enhance bioavailability for oral administration.
- Nanoparticle Suspensions: Improve delivery efficiency in reproductive health applications.
- Combination Therapies:
- Synergistic effects with magnesium sulfate in managing preeclampsia 2.
For detailed toxicology data or synthesis protocols, consult regulatory databases (e.g., FDA, EMA) or specialized pharmacological references.
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