Progesterone Powder CAS 57-83-0

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October 22, 2024

Progesterone powder , a white crystalline powder, soluble in alcohol, acetone, and dioxane, slightly soluble in vegetable oil, insoluble in water. Also known as progesterone or progesterone, it is the main biologically active progesterone secreted by the ovaries, with the chemical formula C21H30O2. Before ovulation, the daily amount of progesterone produced is 2-3 mg, mainly from the ovaries.

After ovulation, it rises to 20-30mg per day, mostly secreted by the corpus luteum in the ovaries. Progesterone can protect the endometrium of women. During pregnancy, progesterone can provide support and guarantee for the early growth and development of the fetus, and can also have a certain calming effect on the uterus. In addition, the relationship between progesterone and estrogen is inseparable, and both are quite important female hormones. The main function of estrogen is to promote the development and maturation of secondary sexual characteristics in women, while progesterone further promotes the development and maturation of secondary sexual characteristics based on the action of estrogen, and there is a synergistic effect between the two.

Progesterone powder is an estrogen steroid hormone with multiple chemical uses.
1. Pharmaceutical preparations:
Progesterone, as a compound of drugs, is used for various purposes in clinical practice. For example, it is used as an alternative therapy to supplement or regulate the lack of progesterone levels in women's bodies. In addition, progesterone is also used to treat infertility, promote pregnancy, and in assisted reproductive technology.

2. Contraceptive pills:
Progesterone is used as an active ingredient in contraceptive pills. When progesterone is supplied to women in the form of a drug, it can inhibit ovulation and alter the endometrium, thereby reducing the likelihood of pregnancy.
3. Cosmetics and skincare products:
Progesterone is widely used in certain cosmetics and skincare products. It is believed to have moisturizing, antioxidant, and anti-aging effects on the skin. Therefore, some skincare products may add progesterone to improve skin quality and reduce the appearance of wrinkles.
4. Analytical Chemistry:
Progesterone is also used as a standard substance for analytical chemistry and drug testing. It can be used as a reference material to verify the accuracy of the instrument and is used in techniques such as mass spectrometry and high-performance liquid chromatography (HPLC).

Method 1

A. Preparation of etherified compounds:

In a 1000ml three necked bottle, add 100g of 4AD, 200ml of ethanol, 80ml of triethyl orthoformate, and 2g of p-toluenesulfonic acid. Stir at 20-25 ℃ for 12-16 hours, and detect the reaction endpoint by TLC. After the reaction is completed, add 3ml of pyridine, stir for 20-25 minutes to neutralize the acid. Then, cool the system to -5-0 ℃, stir for crystallization for 2-3 hours, filter, wash with a small amount of ethanol, merge the washing solution and filtrate, recover the solvent, and mix with the crude product; The filter cake was dried below 70 ℃ to obtain 101.6g of etherified substance, with an HPLC content of 99.2% and a weight yield of 101.6%.

B. Preparation of nitro compounds:

Add 100g of etherified substance, 400ml of nitroethane, and 5ml of ethylenediamine to a 1000ml three necked bottle, stir at 85-90 ℃ for 6-8 hours, and detect the reaction endpoint by TLC. After the reaction is completed, reduce pressure and concentrate to recover nitromethane for reuse. Add 800ml of alcohol to the above residual night, heat to dissolve it, add 5g of activated carbon, reflux decolorize for 1-1.5 hours, filter while hot, soak the filter cake with about 80ml of alcohol, combine the filtrate and washing solution, concentrate at atmospheric pressure to recover about 85% alcohol, then add 500ml of pure water, continue to steam out about 150ml of solvent containing 50-60% ethanol, then cool the system to 5-10 ℃, stir for crystallization for 2-3 hours, and filter, The filter cake was washed with a small amount of 50% ethanol solution and dried below 70 ℃ to obtain 104.6g of nitro compounds, with an HPLC content of 99.2% and a total yield of 104.6% by weight.

C. Preparation of Progesterone powder :

In a 1000ml three necked bottle, add 100g of nitro compounds and 500ml of ethanol. Stir at room temperature and add 60g of zinc powder. Slowly raise the temperature to 60-65 ℃, then add 240ml of 30% hydrochloric acid solution dropwise for about 1.5-2 hours. After the drop is completed, react with insulation for 4-5 hours. After the reaction is completed, reduce pressure distillation to recover about 90-95% of ethanol. Then, add 600ml of tap water, cool to 10-15 ℃, stir for crystallization for 2-3 hours, filter, and wash with water until neutral, Dry the filter cake below 70 ℃ to obtain crude progesterone. Dissolve the crude product of progesterone into 600ml of alcohol, add 5g of activated carbon, heat up and reflux for 1-1.5 hours, filter while hot, wash the filter cake with 100ml of alcohol, merge the washing solution and filtrate, concentrate and recover about 90% of alcohol at atmospheric pressure, then cool to -5-0 ℃, freeze and crystallize for 2-3 hours, filter, wash the filter cake with a small amount of alcohol, and dry below 70 ℃ to obtain 84.2g of progesterone, with a melting point of 129.5-130.5 ℃, an HPLC content of 99.7%, and a yield of 84.2%. Use mother liquor recovery solvent and crude product.

Method 2:

S1: Synthesis of Compound 2, 100g of Compound 1 (a derivative of 4AD), tetramethylpiperidine oxide, dissolved in 3V dichloromethane in a 2L single necked bottle, stirred, added with an aqueous solution of sodium bromide and sodium bicarbonate, and then added with a solution of 10V sodium hypochlorite. Stir at 25 ℃ for 16-20 hours, TLC detected that the raw material reaction is complete. Separate the solution, extract twice with 300mL of dichloromethane, merge the organic phases, wash once with water, concentrate to dryness, and entrain twice with methanol, Add 10V methanol again, concentrate to a volume of 3-5 V, stir, add 7V of water dropwise, filter, and dry at 50 ° C to obtain 90g of compound 2, HPLC>98;

S2: Synthesis of compound 3: Under nitrogen protection: 1- (1-piperidinyl) cyclohexene (self-made) was added with 2V acetonitrile, heated to 65-68 ℃ for dissolution, then compound 2 was added, stirred until dissolved, cooled to 42 ℃, stirred for 10-16 hours, cooled to -20 ℃ (in the laboratory refrigerator), crystallized for 2 hours, filtered, and then beaten once with 2V cold acetonitrile at -5 ℃ -0 ℃, stirred for 2 hours, filtered, and naturally dried to obtain 108g of compound 3;

S3: Synthesis of progesterone. Under nitrogen protection, add 5g of cuprous chloride and 500ml of DMF to a three necked bottle, heat to 65 ° C for dissolution, stir for 1 hour, set aside. Under nitrogen protection, add compound 3 and dichloromethane to the three necked bottle, stir for dissolution, and cool to -20 ° C. Pour in the prepared DMF solution of cuprous chloride, pass through air, and maintain stability at 5-8 ° C. Stir for 16-24 hours, and TLC detects that the remaining 1% of the raw material is below, Lower the temperature to 0-5 degrees Celsius, add 200mL of 10% dilute sulfuric acid solution, stir for 30 minutes, add 300mL of dichloromethane and 300Ml of water, stir for 15 minutes, and separate the solution. Extract the aqueous phase with 200mL of dichloromethane once, combine dichloromethane and concentrate it to about 1 volume of the system. Replace it with methanol (200ml) twice, concentrate to about 1.5 volume of the system, then add 5V of water dropwise at room temperature. Freeze for 1-2 hours in the refrigerator, filter, rinse with a cold methanol solution, and bake at 55 ℃, Obtain 85g of crude progesterone;

S4: Impurity removal and purification of Progesterone powder: In a reaction flask, add dichloromethane, crude progesterone, add 5V sodium hypochlorite, stir until compound 2 is detected by HPLC. Compound 3 is less than 0.1%, separate the solution, extract twice with dichloromethane (100 * 2), wash once with 200ml of 10% sodium thiosulfate, wash once with saturated salt water, add activated carbon, raise the temperature to 35 ° C, stir for decolorization for 1 hour, and filter the system into a clean area for reaction and concentration, In the later stage, use methanol twice, each time using about 2V methanol, control the temperature at 50 ℃, concentrate to a viscous state, reduce the temperature and crystallize for 1 hour, filter, wash the filter cake with a small amount of methanol, drain, wash with water, drain, dry the filter cake at 50-60 ℃ for 12 hours, take samples for testing, load after passing the test, and the yield is 80%.

1. Neurological discomfort: Some women may experience dizziness, headaches, or migraines after taking this substance, which is caused by the medication's adjustment of hormone levels in the body.
2. Breast changes: It may cause changes in breast tissue, resulting in breast tenderness, tenderness, or swelling. This discomfort is usually more pronounced in the early stages of drug use.
3. Gastrointestinal reactions: It may cause certain irritation to the gastrointestinal tract, leading to symptoms such as nausea, vomiting, abdominal pain, diarrhea, etc. The degree of these reactions varies from person to person, and some patients with poor gastrointestinal function may have more severe symptoms.
4. Emotional fluctuations: Due to the impact of this substance on the endocrine system, some people may experience emotional fluctuations such as anxiety, depression, and other changes in emotional states.
5. Weight and fluid changes: Long term use may lead to weight gain or loss, as well as swelling and other symptoms.
6. Abnormal reproductive system: It may cause symptoms such as breakthrough bleeding, vaginal spotting, or irregular vaginal bleeding. In addition, it may also cause changes in the characteristics of cervical secretions and increase the risk of vaginal fungal infections.
7. Allergic reactions: Some patients may experience allergic reactions to the substance, manifested as rash, itching, urticaria, and other symptoms. Severe allergic reactions may require immediate medical attention.
8. Liver and kidney injury: It requires metabolism and excretion through the liver and kidneys. Therefore, long-term or excessive use may cause certain damage to the liver and kidneys. It is recommended that patients regularly check their liver and kidney function while taking progesterone powder.
9. Other side effects: It may also cause side effects such as fever, insomnia, and changes in sexual desire. In addition, for pregnant women, using a large amount of progesterone in early pregnancy may increase the risk of fetal deformities in the spine, anus, limbs, and other areas.

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