Gestodene
Gestodene
CAS: 60282-87-3
Molecular Formula: C21H26O2
Gestodene - Names and Identifiers
Gestodene - Physico-chemical Properties
| Molecular Formula | C21H26O2 |
| Molar Mass | 310.43 |
| Density | 1.15±0.1 g/cm3(Predicted) |
| Melting Point | 190-192°C |
| Boling Point | 462.7±45.0 °C(Predicted) |
| Flash Point | 196.9°C |
| Solubility | DMSO: >20mg/mL |
| Vapor Presure | 1.66E-10mmHg at 25°C |
| Appearance | powder |
| Color | white to off-white |
| Maximum wavelength(λmax) | ['240nm(MeOH)(lit.)'] |
| Merck | 14,4413 |
| pKa | 12.16±0.40(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.588 |
| Physical and Chemical Properties | Crystallization from acetone-hexane, melting point 197.9 °c. [Α] D22-185.7 °(C = 0.5, chloroform). |
| Use | Used as an antiprogestin |
Gestodene - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 62 - Possible risk of impaired fertility |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | JF7956000 |
| HS Code | 29144000 |
Gestodene - Reference
| Reference Show more | 1. [IF=7.514] Suo Decheng et al."Trace analysis of progesterone and 21 progestins in milk by ultra-performance liquid chromatography coupled with high-field quadrupole-orbitrap high-resolution mass spectrometry."Food Chem. 2021 Nov;361:130115 |
Gestodene - Nature
Open Data Verified Data
crystallized from acetone-hexane, melting point 197.9 °c.
Last Update：2024-01-02 23:10:35
Gestodene - Preparation Method
Open Data Verified Data
with 18-methyl Estrin -4-ene -3,17-= ketone as a raw material, the introduction of hydroxyl group in the 15 position by fermentation. Dissolve in pyridine, add methanesulfonyl chloride, after reaction add dimethylformamide and anhydrous sodium acetate. Then in the mixture of tetrahydrofuran and hexane, in the presence of n-butyl lithium, acetylene is introduced, and ethynylation is carried out to obtain gestodene. Alternatively, 18-methyl Estrin -4-ene -3 ,17-= ketone is used as a raw material, and a hydroxyl group is introduced at position 15 by fermentation. Acylation with acetic anhydride in pyridine followed by etherification. Ethynylation is then carried out in the presence of n-butyl lithium in tetrahydrofuran via acetylene. Finally, under the action of hydrochloric acid, gestodene was obtained.
Last Update：2022-01-01 09:23:57
Gestodene - Use
Open Data Verified Data
progesterone, which is 2 times more active than levonorgestrel, has no androgen and estrogen activity, and has anti-estrogen effect. The effect is strong and the use dose is low, the contraceptive effect is reliable, the cycle control is good, and the lipid metabolism can have a beneficial effect.
Last Update：2022-01-01 09:23:57
Gestodene - Reference Information
| adverse reactions | Nausea of the common ones of gestrinone were Nausea, Vomit, Head Pain, breast pain, small amount of bleeding between the menses; less common are rash and can not tolerate contact lenses; More serious adverse reactions are thrombosis, increased blood pressure, liver disease, jaundice and allergic reactions. |
| biological activity | gestoene (SH B 331) is a progestogen contraceptive. |
| Use | progestin, acting more strongly than the other 19 desmethyltestosterone derivatives, has few androgenic effects within the effective dose. And ethinyl estradiol constitute a new combination oral contraceptive. use as antiprogestin |
| production method | Method 1: in the form of 18-methyl estrane-4-ene-3, 17-diketone as raw material. A 20L glass fermenter was filled with 15L of sterile solution. The composition of the solution was as follows: 3% glucose, 1% corn flour, 0.2% sodium nitrate, 0.1% potassium dihydrogen phosphate, 0.2% dipotassium hydrogen phosphate, 0.05% magnesium sulfate, 0.002% iron (II) sulfate and 0.05% potassium chloride. 10490 of Penicillium sp. (ATCC) cultured for 72H in a shaking flask were implanted and cultured for 24h at 30 ° C. With stirring and air bubbling. Under sterile conditions, 1.8L of this broth was transferred into a 50L fermenter containing 30L of a solution of the same composition as the sterile solution described above. After 12h of incubation, a solution of 120g of tween-80 salt of 18-methylestrine-4-ene-3, 17-Dione suspended in 2L of distilled water was added, the cells were further cultured for 70H under the same conditions. The extract was then extracted with methyl isobutyl ketone and concentrated in vacuo. The residue was reacted with activated carbon, and then recrystallized from ethyl acetate to obtain 77.2% G of compound (I) with a melting point of 179.9 ° C. In a yield. 827g (3.5 mmol) of the compound (I) was dissolved in of pyridine, and of methanesulfonyl chloride was added dropwise at 0 °c for 10min. 350ml of dimethylformamide and 283g of anhydrous sodium acetate were added and stirred at room temperature for 20H under an argon atmosphere. The reaction solution was poured into ice water, and the precipitated precipitate was collected by filtration, washed with water, and dried under vacuum. 212G of the obtained crude product was dissolved in 1500ml of ethyl acetate and 0.4ml of pyridine, and 21.0G of activated carbon was added to decolorize. It was concentrated to 420ml and left to crystallize at 0 °c. 188g of compound (II) was obtained by filtration, Yield 80%, melting point 156.9 °c (recrystallized from acetone-hexane). To a mixture of 240ml of tetrahydrofuran and 60ml of hexane, acetylene was applied for 15min at -70 °c. A solution of 288 (15% mmol) of n-butyllithium (hexane solution) in of tetrahydrofuran was added dropwise under argon. After 10min, a solution of 30.0g(106 mmol) of compound (II) in of tetrahydrofuran was added. The feeding of acetylene was continued for 1H at -70 °c with stirring. 150ml of methanol and 45ml of concentrated hydrochloric acid were added, and after stirring at room temperature for 1H, 375ml of water was added. After concentration in vacuo, the crystals were left at 0 °c. Filter, wash with water, and dry. Chromatography with 0-50% ethyl acetate/hexane and recrystallization from ethyl acetate gave 18.4g of gestodene in 56% yield with a melting point of 198 °c. Method 2: with the same 18-methyl estrol -4-ene -3,17-Dione as the raw material, and the same as method 1, the introduction of hydroxyl compounds by fermentation (I). 330g (mmol) of the compound (I) was dissolved in of pyridine and of acetic anhydride was added dropwise. After addition, the reaction was continued for 1H. The reaction solution was poured into ice water, and the precipitated precipitate was collected by filtration, washed with water until neutral, and dried under vacuum at 50 ° C. To obtain 109.3G of compound (III) in a yield of 96%. After recrystallization from acetone-hexane, the melting point was 165.5 °c. 48.0g(139 mmol) of compound (III) and g of pyridine salt of p-toluenesulfonate were dissolved in of 2, 2-dimethoxypropane and stirred for 6h under reflux. Slow cooling to -20 °c. After 4H, the crystals were collected by filtration, washed several times with a small amount of cold methanol, and dried under vacuum to give 42.0G of compound (IV) in 84% yield. After recrystallization from acetone-hexane, the melting point was 194 °c. To 200ml(320 mmo1) N-butyl lithium (15% in hexane) in a solution of anhydrous tetrahydrofuran was ethenylated at 0 °c for 30min. The lithium acetylene solution thus obtained was added dropwise to a solution of 20.0g(56 mmol) of compound (IV) in of anhydrous tetrahydrofuran at 0 °c under argon. 80ml of semi-concentrated hydrochloric acid was added slowly and stirred at 0 °c for 10min. Extract with ethyl acetate, extract water, dry, activated carbon decolorization. Recrystallization from about. 50ml of methanol yielded 13.0g of pregnenoldione in yield. 75%, the melting point of 197. Method 3: The carbonyl group at position 3 in compound (I) is reacted with Ketal or thioketal, and lithium acetylene or magnesium bromide acetylene is introduced into acetylene, and then Ketal is removed to obtain gestodene. The 18-methyl estrol -4-ene -3,17-Dione is selectively oxidized to introduce a hydroxyl group at the 15-position; And reacted with 2, 2-dimethylpropanediol, it is protected by forming a Ketal at the 3-position; Reacting with trimethylsilyl chloride or acetic anhydride to form a trimethylsilyloxy or acetyloxy group at the 15-position; Then reacting with acetylene magnesium bromide, ethynyl was introduced at position 17, After hydrolysis and dehydration under the action of oxalic acid, gestodene was obtained. It is also possible to dehydrate the olefinic bond prior to the introduction of the ethynyl group. 7.5g of magnesium and 24ml of bromoethane were reacted in 140ml of tetrahydrofuran to obtain ethyl magnesium bromide. Further, 300ml of tetrahydrofuran was added, and acetylene was introduced into the reaction solution for about 40min Under cooling in an ice bath. Add Dropwise 5g of 18-methyl -3,3-(2, 2-dimethyl-1, 3-propanedioxy)-5,15-and -5(10), A solution of 15-estradien-17-one in 200ml of tetrahydrofuran. After addition, the mixture was stirred at room temperature for 2H. Ammonium chloride solution was added carefully and diluted with ether. The separated organic layer was continuously washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Chromatography on silica gel and 2.5% ~ 2.9% acetone/hexane gave 3.1g of 17 α-ethynyl -18-methyl -3,3-(2, 2-dimethyl-1, 3-prosubunit dioxy)-5,15-and -5(10),15-estradien-17β-OL. The compound was vigorously stirred with 70ml of methanol, 14ml of water and 2.3g of oxalic acid for 40min. The reaction solution was diluted with ether, washed with water until neutral, and dried. Recrystallization from acetone-hexane gave g of gestodene, melting point 154 °c. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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