β-ESTRADIOL Chemical Properties
- Melting point:
- 178-179 °C(lit.)
- D25 +76 to +83° (dioxane)
- Boiling point:
- 355.44°C (rough estimate)
- 1.0708 (rough estimate)
- refractive index
- 80.4 ° (C=1, Dioxane)
- Flash point:
- storage temp.
- Practically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent), slightly soluble in methylene chloride.
- pKa 10.71±0.02(H2O(0.1% p-dioxane) t=25±0.1 I=0.03(KCl))(Approximate)
- White to off-white
- Water Solubility
- Soluble in dimethyl sulfoxide, ethanol , water, phosphate buffer saline, dimethyl formamide, acetone, dioxane and alkali hydroxides. Slightly soluble in vegetable oils.
- Stable. Incompatible with strong oxidizing agents.
- CAS DataBase Reference
- 50-28-2(CAS DataBase Reference)
- NIST Chemistry Reference
- EPA Substance Registry System
- Estradiol (50-28-2)
- Hazard Codes
- Risk Statements
- Safety Statements
- WGK Germany
- HS Code
- Hazardous Substances Data
- 50-28-2(Hazardous Substances Data)
- LD50 subcutaneous in rat: > 300mg/kg
β-ESTRADIOL Usage And Synthesis
Indications and Usage
Estradiol is a white or milky white ordorless crystalline powder. It is soluble in dioxane and acetone, slightly soluble in ethanol, and insoluble in water.
Estradiol is the intermediate between estradiol valerate and estradiol benzoate, and it is a type of estrogen drug. It can be used to treat uterine functional bleeding, primary amenorrhea, menopausal syndrome, and prostate cancer. Estradiol can promote and adjust the normal growth of female sex organs and secondary sex characteristics, promote mammary duct maturation and growth, and aid in posseting. Estradiol can also be used in biochemical research.
In high dosages, estradiol can inhibit the release of anterior pituitary prolactin, thus decreasing breast milk secretion. However, nausea, vomiting and endometrial hyperplasia-induced bleeding may occur. Patients with liver or kidney failure should use with caution.
Do not use on breasts, vaginal area and vaginal mucosa.
White or almost white, crystalline powder or colourless crystals.
Estradiol, 17-β-is an odorless white to yellow crystalline substance.
Potent mammalian estrogenic hormone produced by the ovary.
Estradiol is the major estrogen secreted by the premenopausal ovary.
Estradiol USP (Estrace) is used to treat Breast cancer; prostatic carcinoma.
ChEBI: The 17beta-isomer of estradiol.
Estradiol, estra-1,3,5(10)-triene-3,17β-diol, is the most activeof the natural steroid estrogens. Although its 17β-OHgroup is vulnerable to bacterial and enzymatic oxidation toestrone, it can be temporarily protected as anester at C3 or C17, or permanently protected by adding a17α-alkyl group (e.g., 17α-ethinyl estradiol, the most commonlyused estrogen in oral contraceptives). The increasedoil solubility of the 17β-esters (relative to estradiol) permitsthe esters to remain in oil at the IM injection site for extendedperiods. These derivatives illustrate the principles of steroidmodification. Transdermal estradiolproducts avoid first-pass metabolism, allowing estradiol tobe as effective as oral estrogens for treating menopausalsymptoms. A new transdermal spray, Evamist, was approvedin 2007. Estradiol itself is typically not very effective orallybecause of rapid metabolism, but an oral formulation of micronizedestradiol that allows more rapid absorption of thedrug is available (Estrace). In addition to the oral and transdermalproducts, estradiol is also available in gel, cream, andvaginal ring formulations. The commercially available estradiolesters are the following:
Estradiol 3-acetate, USP (oral; vaginal ring)
Estradiol 17-valerate, USP (IM injection)
Estradiol 17-cypionate, USP (IM injection).
A carcinogen (OSHA).
Endogenous estrogen receptor (ER) agonist (K i values are 0.12 and 0.13 nM for ER α and ER β respectively). Also high affinity ligand at membrane estrogen GPR30 receptors.
Natural estradiol, used in transdermal systems for hormonal substitution, can induce allergic contact dermatitis, with the risk of systemic contact dermatitis after oral reintroduction.
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. A promoter. Human reproductive effects by ingestion: ferthty effects. Experimental reproductive effects. Human mutation data reported. A steroid hormone much used in medicine. When heated to decomposition it emits acrid smoke and irritating fumes.
The working environment may be contaminated during sex hormone manufacture, especially during the extraction and purification of natural steroid hormones; grinding of raw materials; handling of powdered products and recrystallization. Airborne particles of sex hormones may be absorbed through the skin, ingested or inhaled. Enteric absorption results in quick inactivation of sex hormones in the liver. The rate of inactivation is decreased for the oral, alkylated steroid hormones (methyl testosterone, anabolic steroids, etc.). Sex hormones may accumulate and reach relatively high levels even if their absorption is intermittent. Consequently, repeated absorption of small amounts may be detrimental to health. Intoxication by sex hormones may occur in almost all the exposed workers if preventive measures are not taken. The effect in the industrial sector is more successful than the agricultural one (chemical caponizing of cockerels by stilbestrol implants and incorporation of estrogens in feed for body weight gain promotion in beef cattle), where measures taken are summary and the number of cases of intoxication is consequently bigger
UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials
17-Estradiol (previously known as -estradiol) is purified by chromatography on SiO2 (toluene/EtOAc 4:1) and recrystallised from CHCl3/hexane or 80% EtOH. It is stable in air, is insoluble in H2O, and is precipitated by digitonin. The UV has max at 225 and 280 nm. The diacetate [3434-88-6] has m 97-98o and forms leaflets from aqueous EtOH. The 3-benzoate crystallises from aqueous MeOH withm 193o and  D 25 +58o to 63o (c 1, dioxane). [Meischer & Scholz Helv Chim Acta 20 263, 1237 1937, Biochem J 32 1273 1938, Oppolzer & Roberts Helv Chim Acta 63 1703 1980, Inhoffen & Zühlsdorff Chem Ber 7 4 1914 1941, Beilstein 6 IV 6611.]
- 1,3,5(10)-ESTRATRIEN-3,15-ALPHA, 16-ALPHA, 17-BETA-TETROL TETRA ACETATE
- BETA-ESTRADIOL-6-ONE 6-(O-CARBOXYMETHYLOXIME)
- 1,3,5(10)-ESTRATRIEN-3,17-BETA-DIOL 17-ACETATE, 3-METHYL ETHER
- 1,3,5-ESTRATRIENE-3,16ALPHA,17BETA-TRIOL 3-GLUCURONIDE SODIUM SALT
- ESTRIOL TRIACETATE
- 1,3,5-ESTRATRIENE-3,17BETA-DIOL 3-GLUCURONIDE 17-SULFATE DIPOTASSIUM SALT
- Ethynyl estradiol
- ESTRIOL TRISULFATE TRISODIUM SALT
- 1,3,5(10)-ESTRATRIEN-2,3,17-BETA-TRIOL 17-ACETATE
- 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether
- BETA-ESTRADIOL 3-METHYL ETHER
- ESTRADIOL, 17B-,CIS-ESTRADIOL,B-ESTRADIOL,BETA-ESTRADIOL
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