Ethinylestradiol Ethinylestradiol
Structural formula
| Business number | 018U |
|---|---|
| Molecular formula | C20H24O2 |
| Molecular weight | 296.41 |
| label |
17α-Ethyne-1,3,5-(10)-estrotriene-3,17β-diol, 17α-Ethynyl-1,3,5(10)-estratriene-3,17β-diol |
Numbering system
CAS number:57-63-6
MDL number:MFCD00003690
EINECS number:200-342-2
RTECS number:RC8925000
BRN number:2419975
PubChem number:24894585
Physical property data
1. Properties: White to milky white crystalline powder. Odorless.
2. Density (g/mL, 25/4℃): 1.1460
3. Relative vapor density (g/mL, air=1): Undetermined
4. Melting point (ºC): 145-146℃ (hemihydrate). 182-184℃ (anhydrous)
5. Boiling point (ºC, normal pressure): Undetermined
6. Boiling point (ºC, 5.2kPa): Undetermined
7. Refractive index: Undetermined
8. Flash point (ºC): Undetermined
9. Specific rotation (º): Undetermined
10. Autoignition point or ignition temperature (ºC): Undetermined
11. Vapor pressure (kPa, 25ºC): Undetermined
12. Saturated vapor pressure (kPa, 60ºC): Undetermined
13. Heat of combustion (KJ/mol): Undetermined
14. Critical temperature (ºC): Undetermined
15. Critical pressure (KPa): Undetermined
16. The logarithmic value of the oil-water (octanol/water) partition coefficient: Undetermined
17. Explosion upper limit (%, V/V): Undetermined
18. Lower explosion limit (%, V/V): Undetermined
19. Solubility: Soluble in ethanol��, propanol, ether, chloroform, dioxane, vegetable oil and sodium hydroxide solution are almost insoluble in water.
Toxicological data
None
Ecological data
None
Molecular structure data
1. Molar refractive index: 86.26
2. Molar volume (m3/mol): 244.4
3. Isotonic specific volume (90.2K): 672.4
4. Surface tension (dyne/cm): 57.2
5. Polarizability (10-24cm3): 34.19
Compute chemical data
1. Reference value for hydrophobic parameter calculation (XlogP): 3.7
2. Number of hydrogen bond donors: 2
3. Number of hydrogen bond receptors: 2
4. Number of rotatable chemical bonds: 7
5. Number of tautomers: 9
6. Topological molecular polar surface area (TPSA): 40.5
7. Number of heavy atoms: 22
8. Surface charge: 0
9. Complexity: 505
10. Number of isotope atoms: 0
11. Determine the number of atomic stereocenters: 5
12. Number of uncertain atomic stereocenters: 0
13. Determine the number of stereocenters of chemical bonds: 0
14. Number of uncertain chemical bond stereocenters: 0
15. Number of covalent bond units: 1
Properties and stability
None
Storage method
Stored in inert gas.
Synthesis method
Obtained from the ethynylation of estrone (C18H22O2, [53-16-7]): Heat toluene isobutanol, potassium hydroxide and isobutanol under reflux and azeotropic dehydration for 8 hours, add tetrahydrofuran, and heat at 25-40℃ Pour acetylene down to the required amount. Add estrone tetrahydrofuran solution and continue to pass acetylene at 5-10°C for 12 hours. Use 30% sulfuric acid to adjust the slight acidity below 40°C, and recover tetrahydrofuran under reduced pressure. Remove the residual solution by steam distillation, cool, filter, wash with water until neutral, and dry at 80°C to obtain crude ethinyl estradiol. After recrystallization from ethanol and decolorization of activated carbon, the finished product is obtained. The yield is 85%.
Purpose
This product is an estrogen drug. It has the same effect as diethylstilbestrol, but is 20 times more potent. Used in combination with progestogen-based contraceptives, it has a synergistic effect in inhibiting ovulation, can enhance contraceptive efficacy, and can reduce side effects such as breakthrough bleeding. In addition, it can also be used for menstrual disorders such as amenorrhea, oligomenorrhea, menopausal syndrome and uterine hypoplasia. For preparation of contraceptive pills.
