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Estrone powder, with the molecular formula C₁₈H₂₂O₂ and CAS number 53-16-7, is a steroidal compound that typically appears as a white plate-like crystal or crystalline powder. It exhibits good stability under normal atmospheric conditions and does not readily decompose when exposed to air.
Its physicochemical properties are well-defined: the melting point ranges from 256–262 °C. The specific rotation values are recorded as [α]²⁵ᴰ +158° to +168° in dioxane and [α]²²ᴰ +152° in chloroform (0.995% concentration). In ethanol solution, estrone shows a characteristic maximum ultraviolet absorption at 287 nm, which is often used for qualitative and quantitative analysis in laboratory testing.
In terms of solubility, estrone is almost insoluble in water, but dissolves in dioxane, pyridine, and aqueous alkali hydroxide solutions. It is slightly soluble in ethanol (approximately 1:400), acetone, benzene, chloroform, diethyl ether, and vegetable oils. These solubility differences are closely related to estrone's molecular structure and polarity.The molecule contains multiple nonpolar structural segments, resulting in stronger interactions with organic solvents. In contrast, as a highly polar solvent, water forms only weak intermolecular forces with estrone, leading to its low aqueous solubility.
Beyond its well-known physiological functions, estrone also shows promising application value in several industrial and agricultural fields.In the food industry, it has been investigated as a potential functional additive to improve the nutritional profile of foods.For instance, adding estrone to dairy products may enhance calcium absorption efficiency, thereby supporting bone health and skeletal development in consumers.
Nevertheless, the application of estrone in food must strictly comply with national and international regulations and safety standards to ensure product safety and legality.
Estrone also has practical uses in animal husbandry, where it can be employed to promote growth, development, and reproductive performance in livestock. In agricultural production, it has been studied for its ability to improve crop yield and quality through regulatory effects on plant physiological processes.With ongoing scientific advancements and in-depth mechanistic research, the application scope of estrone is expected to expand further, revealing broader and more valuable prospects across multiple disciplines.
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Chemical Formula |
C18H22O2 |
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Exact Mass |
270 |
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Molecular Weight |
270 |
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m/z |
270 (100.0%), 271 (19.5%), 272 (1.8%) |
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Elemental Analysis |
C, 79.96; H, 8.20; O, 11.83 |
Estrone powder, as an important estrogen compound, has shown extensive application value in multiple fields.
(1) Estrogen replacement therapy: Estrogen is often used as a drug for estrogen replacement therapy due to its structure and function being similar to natural estrogen. It can help regulate endocrine balance and treat various symptoms caused by decreased estrogen levels, such as menopausal syndrome and estrogen deficiency. The supplementation of estrone can alleviate menopausal symptoms such as hot flashes, sweating, and emotional fluctuations, and improve the quality of life of patients.
(2) Regulating menstruation: Estrogen has a significant impact on the female reproductive system, promoting endometrial hyperplasia and shedding, leading to periodic menstruation. Therefore, it is often used to treat various functional disorders caused by menstrual disorders, reduced menstruation, and amenorrhea. By supplementing with estrone, women can effectively regulate their menstrual cycle and improve symptoms of menstrual disorders.
(3) Preventing osteoporosis: Estrogen plays an important role in bone health, maintaining bone density and strength. Estrogen, as a type of estrogen, has a positive effect on preventing osteoporosis. By supplementing with estrogen, bone density can be increased and the risk of fractures can be reduced, especially for menopausal women, whose preventive effect on osteoporosis is more significant.Contraceptive drugs and reproductive health.Estrogen has the ability to regulate the menstrual cycle and inhibit ovulation, making it widely used in the fields of contraceptives and reproductive health. It can serve as an important ingredient for synthesizing oral contraceptives and other contraceptive products, effectively preventing unintended pregnancies.
2.Other Fields
Estrogen has also been widely used in scientific research and laboratories. It is often used as a tool compound for studying cell biology, hormone activity, and physiological effects. Researchers can use estrone to explore the mechanisms and effects in related fields, further understanding the human physiology and disease development process. In addition, estrone can also be used to prepare estrogenic derivatives such as estriol, providing important raw materials for related research and applications.
Estrogen also has certain application value in the field of cosmetics. It has antioxidant and whitening effects, which can delay skin aging and improve uneven skin tone. Therefore, estrone is often added to skincare and cosmetics to improve their efficacy and quality. However, it should be noted that due to estrone being a steroid compound, its use in cosmetics should strictly control its dosage and concentration to avoid potential side effects and risks.
Estrogen also has certain applications in the food industry. As a food additive, it can be used to enhance the nutritional value of food. For example, adding estrone to dairy products can enhance their calcium absorption capacity and help improve human bone health. However, it should also be noted that the use of estrone in the food industry should comply with relevant regulations and standards to ensure the safety and compliance of the product.
Estrone powder is an important estrogen compound widely used in fields such as medicine and scientific research. There are various synthesis methods for it, and one common method is to prepare it through steps such as halogenation, cyclization, and dehalogenation of androdienedione (ADD).
Synthesis steps
Firstly, add reaction solvents (such as ethanol, ether, etc.), phase transfer catalysts (such as tetrabutylammonium bromide, tetrabutylammonium chloride, etc.), and androdienedione (ADD) as raw materials to the reaction vessel in a certain proportion. Then, turn on the agitator and stir for 20-60 minutes to fully mix and disperse the raw materials and catalyst in the solvent
ADD+solvent+phase transfer catalyst → mixture
While stirring, slowly add halogen elements (such as bromine, iodine, etc.) to the reaction mixture, and add organic phosphines (such as triphenylphosphine, triethylphosphine, etc.) as co catalysts. Halogen elements will undergo an addition reaction with the carbon carbon double bond of androdienedione, generating halogenated products. This step is usually performed at room temperature, but the reaction rate can also be increased by heating.
ADD + Br2→ ADD-Br2
Cyclization reaction
After the halogenation reaction is completed, acid binding agents (such as potassium carbonate, sodium bicarbonate, etc.) are added to the reaction mixture to neutralize the acidic substances produced during the reaction. Then, heat the reaction mixture to 50 ℃ to 80 ℃, causing the halogenated products to undergo cyclization reaction, generating cyclic intermediate products. This step requires strict control of temperature and time to ensure the smooth progress of the cyclization reaction.
Halogenated ADD+acid binding agent → cyclization intermediate product
Dehalogenation reaction.After the cyclization reaction is completed, continue to heat the reaction mixture to cause the intermediate products of cyclization to undergo dehalogenation reaction, generating estrone. Dehalogenation reactions usually need to be carried out at higher temperatures to promote the progress of the reaction. Meanwhile, the rate of dehalogenation reaction can be accelerated by adding reducing agents such as zinc powder, iron powder, etc.Intermediate products of cyclization+reducing agent → estrone+halide
Post processing.After the reaction is completed, cool the reaction mixture to room temperature and remove solid impurities generated during the reaction through filtration. Then, dry the filtrate to remove solvents and moisture. Finally, pure products are obtained through methods such as crystallization and recrystallization.Reaction mixture → filtration → drying → C18H22O2
The synthesis method of estrone powder involves steps such as halogenation, cyclization, and dehalogenation to convert androstenedione into C18H22O2. This method has the advantages of easy availability of raw materials, mild reaction conditions, and high product purity, making it one of the important methods for preparation. By strictly controlling the reaction conditions and post-treatment process, high-quality products can be obtained to meet the needs of fields such as medicine and scientific research.
What are the side effects of this substance?
Risks of Estrogen Use
Long-term use of estrogen (including estrone) may increase the risk of endometrial cancer, which rises with dosage and duration; this risk can be reduced by concurrent use with progesterone or partial estrogen dose replacement, and there is no such risk for patients who have undergone total hysterectomy. In terms of mental health, patients receiving estrogen therapy may suffer from depression, and some women taking estrogen-containing oral contraceptives may experience severe depression leading to suicidal behavior; patients with a history of depression should be closely observed, and estrogen use should be discontinued if severe depression recurs.
Blood clot risk
The use of estrogen may increase the risk of blood clots, which can lead to stroke, heart attack, or death. These side effects are rare and typically occur in male patients treated with high-dose estrogen for cancer.
Rare side effects
headache (sudden or severe), loss of coordination (sudden), loss or change of vision (sudden), chest pain, groin or leg pain, especially in the lower leg area of the leg, shortness of breath (sudden and inexplicable), slurred speech (sudden), weakness or numbness in the arms or legs.
Other side effects
Excessive use of estrogen may result in the following side effects: breast pain (female and male), increased heart rate, fever, urticaria, hoarseness, breast enlargement (female and male), skin irritation, skin itching, joint pain, stiffness or swelling, rash, skin redness, shortness of breath, swelling of eyelids, face, lips, hands or feet, swelling of lower limbs, chest urgency, difficulty breathing or swallowing, rapid weight gain, wheezing, etc
The impact on the liver
Estrogen may cause bile stasis, manifested as discomfort, decreased appetite, and itching 2 weeks to 2 months after the start of treatment. Occasionally, there may be joint pain, fever, and rash. Serum bilirubin may be between 3-10 mg/dL, mainly conjugated bilirubin. Women with a history of jaundice during pregnancy have an increased risk of jaundice recurrence when using oral contraceptives containing estrogen. If jaundice occurs during estrogen treatment, the medication should be discontinued.
In the late 19th century, scientists began to pay attention to the impact of the ovaries on women's physiological functions. In 1896, German scientist Gustav Jacoby first proposed that the ovaries may secrete a substance that affects female characteristics. Subsequently, British physiologists Ernest Starling and William Bayliss proposed the concept of "hormone" in 1902, laying the foundation for subsequent research. In the 1920s, scientists began attempting to extract active ingredients from animal ovaries. In 1923, American biochemists Edgar Allen and Edward Doisy successfully isolated a substance from mouse ovaries that could cause female animals to estrus, and named it "theelin", later known as estrone. This discovery marks a significant breakthrough in estrogen research. In 1929, German chemist Adolf Butenandt successfully isolated the crystalline form of estrone from the urine of pregnant women and determined its molecular formula as C18H22O2. This achievement made him the first scientist to purify estrogen from natural sources, and as a result, he was awarded the 1939 Nobel Prize in Chemistry (shared with Leopold Ruzicka). At the same time, American scientist Edward Doisy independently extracted estrone from pregnant women's urine and further studied its physiological effects.These studies confirm that estrone is one of the main hormones secreted by the ovaries and placenta, and is crucial for the development and function of the female reproductive system. In the 1930s, scientists devoted themselves to deciphering the chemical structure of estrone.
In 1932, Butenant and German chemist Kurt T ö pfer determined through degradation experiments and X-ray crystallography analysis that the basic skeleton of estrone is cyclopentane and polyhydrophene (steroid structure). In 1938, Swiss chemist Leopold Ruzicka successfully synthesized estrone and further confirmed its structure. This breakthrough not only promoted the industrial production of estrogen, but also laid the foundation for the development of subsequent hormone drugs.
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