50-28-2
- Product Name：Estra-1,3,5(10)-triene-3,17-diol(17b)-
- Molecular Formula：C18H24O2
- Purity：99%
- Molecular Weight：
Product Details;
CasNo： 50-28-2
Molecular Formula： C18H24O2
Appearance： white crystalline powder
High Purity Estradiol Cas No.50-28-2 Export In Bulk Supply
- Molecular Formula:C18H24O2
- Molecular Weight:272.387
- Appearance/Colour:white crystalline powder
- Vapor Pressure:9.82E-09mmHg at 25°C
- Melting Point:178-179 °C(lit.)
- Refractive Index:80.4 ° (C=1, Dioxane)
- Boiling Point:445.917 °C at 760 mmHg
- PKA:pKa 10.71±0.02(H2O(0.1% p-dioxane) t=25±0.1 I=0.03(KCl))(Approximate)
- Flash Point:209.634 °C
- PSA：40.46000
- Density:1.17 g/cm3
- LogP:3.60920
50-28-2 Usage
description
β-Estradiol is an endogenous estrogenic hormone receptor (ER) agonist (Ki values are 0.12 and 0.13 nM for ERα and ERβ respectively). Also high affinity ligand at membrane estrogen GPR30 receptors. β-Estradiol is an activator of PI 3-kinase.Estradiol (17β-estradiol, β-Estradiol, E2, 17β-Oestradiol) is a human sex hormone and steroid, and the primary female sex hormone. Estradiol upregulates IL-6 expression through the estrogen receptor β (ERβ) pathway.
Uses
17β-Estradiol is the major estrogen secreted by the premenopausal ovary.This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.β-Estradiol is used to study cell differentiation and transformations (tumorigenicity).
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.
Adverse reactions
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.
Contradictions
Do not use on breasts, vaginal area and vaginal mucosa.
Chemical Properties
White or almost white, crystalline powder or colourless crystals.
Chemical Properties
Estradiol, 17-β-is an odorless white to yellow crystalline substance.
Uses
17β-Estradiol is the major estrogen secreted by the premenopausal ovary.This compound is a contaminant of emerging concern (CECs). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
Uses
Estradiol is the major estrogen secreted by the premenopausal ovary.
Uses
Estradiol USP (Estrace) is used to treat Breast cancer; prostatic carcinoma.
Application
β-Estradiol has been used:for the in vitro maturation of bovine cumulus-oocyte complexes (COCs)as a supplement in in vitro maturation medium (IVM), which is used as a control mediumin estrogen-induction assay
Definition
ChEBI: The 17beta-isomer of estradiol.
Acquired resistance
Estradiol is the most potent endogenous estrogen, exhibiting high affinity for the ER and high potency when administered parenterally. When administered orally, estradiol is promptly conjugated in the intestine and oxidatively metabolized by the liver, resulting in its low oral bioavailability and therapeutic effectiveness.
General Description
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).
Hazard
A carcinogen (OSHA).
Biological Activity
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.
Contact allergens
Natural estradiol, used in transdermal systems for hormonal substitution, can induce allergic contact dermatitis, with the risk of systemic contact dermatitis after oral reintroduction.
Biochem/physiol Actions
The major estrogen secreted by the premenopausal ovary. Estrogens direct the development of the female phenotype in embryogenesis and during puberty by regulating gene transcription and, thus, protein synthesis. It also induces the production of gonadotropins which, in turn, induce ovulation. Exposure to estradiol increases breast cancer incidence and proliferation.
Mechanism of action
The most potent naturally occurring estrogen in mammals. It is synthesized primarily in the ovary, and also in the testis, adrenal gland and placenta, and to a limited extent by peripheral tissues (e.g., liver, fat, and skeletal muscle) from androstenedione and testosterone. It is responsible for the development of secondary sex characteristics in the female at puberty (i.e., growth and development of the vagina, uterus and fallopian tubes, enlargement of the breasts, and growth and maturation of long bones).
Safety Profile
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.
Synthesis
Estradiol, estra-1,3,5(10)-trien-3,17β-diol (28.1.17), is most easily made by reducing the keto-group of estrone by various reducing agents, in particular potassium borohydride.
Potential Exposure
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
Shipping
UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials
Purification Methods
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.]
InChI:InChI=1/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m0/s1
50-28-2 Relevant articles
ANDROGEN METABOLISM IN MALE AND FEMALE BREAST TISSUE
Perel, E.,Davis, S.,Killinger, D. W.
, p. 345 - 352 (1981)
Incubation studies have been carried out using normal breast tissue and breast tissue from patients with gynecomastia, mammary dysplasia and breast carcinoma to determine the pattern of androstenedione metabolism.
Mechanism of action of bolandiol (19-nortestosterone-3β,17β-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities
Attardi, Barbara J.,Page, Stephanie T.,Hild, Sheri A.,Coss, Christopher C.,Matsumoto, Alvin M.
, p. 151 - 161 (2010)
In immature castrate rats, bolandiol was equipotent to T in stimulating growth of the levator ani muscle but less potent than T in stimulating growth of the sex accessory glands. Bolandiol also stimulated uterine weight increases in immature female rats, which were partly blocked by ICI 182,780, but it was not aromatized in vitro by recombinant human aromatase. In contrast to T, stimulation of sex accessory gland weights by bolandiol was not inhibited by concomitant treatment with the dual 5α-reductase inhibitor dutasteride. As bolandiol exhibits tissue selectivity in vivo, it may act via AR, PR, and/or ER, utilize alternative signaling pathway(s) or transcriptional coregulators, and/or be metabolized to a more potent selective steroid.
Substrate specificity of the placental microsomal aromatase
Gibb,Lavoie
, p. 507 - 519 (1980)
Our data is therefore consistent with the proposal that human placental microsomes contain a single 'high affinity' site for the aromatization of androstenedione and testosterone.
INHIBITION OF ESTROGEN SYNTHESIS IN HUMAN BREAST TUMORS BY TESTOLOLACTONE AND BROMOANDROSTENEDIONE
Budnick, Rose Marie,Dao, Thomas L.
, p. 533 - 542 (1980)
An apparent Km of the aromatase enzyme for androstenedione of 0.08 μM and a Vmax of 23 pmol of estrone synthesized/g tumor/hr were determined for one human breast tumor specimen.These results demonstrate that these aromatase inhibitors may be useful for the treatment of breast cancer.
Thermodynamic Meerwein-Ponndorf-Verley reduction in the diastereoselective synthesis of 17α-estradiol
Ahmed, Gulzar,Nickisch, Klaus
, p. 1 - 4 (2016)
The synthesis of 17α-hydroxy steroids generally requires multiple synthetic manipulations. The synthesis of 17α-estradiol is no exception, as this process involves the protection and release of the 3-hydroxy functional group. The diastereoselective reduction of the 17-keto-steroid can be utilized to prepare 17α-hydroxy-steroids. Here, 17α-estradiol was synthesized from commercially available estrone under thermodynamic Meerwein-Ponndorf-Verley (MPV) conditions in a single step, followed by simple chromatographic separation over silica gel. The remaining mixture of unreacted estrone and estradiols was easily recycled through Oppenauer oxidation to estrone, with an overall yield of 68% 17α-estradiol.
177. The Enantioselective Synthesis of (+)-Estradiol from 1,3-Dihydrobenzothiophene-2,2-dioxide by Successive Thermal SO2-Extrusion and Cycloaddition Reactions
Oppolzer, Wolfgang,Roberts, David Anthony
, p. 1703 - 1705 (1980)
The optically pure steroid (+)-15 has been synthesized from the easily accessible (+)-carboxylic acid 11 by a sequence of 7 steps in 50percent overall yield.The key steps are the regioselective deprotonation/alkylation 7+13->14 and the thermal SO2-extrusion/cycloaddition 14->15 (Scheme 3).The compound (+)-15 has been readily converted to the naturally occurring (+)-estradiol (17) in 60percent yield.
Estramustine binding in rat, baboon and human prostate measured by high pressure liquid chromatography
Kirdani,Corrales,Hoisaeter,Karr,Murphy,Sandberg
, p. 471 - 484 (1981)
The sensitivity of the HPLC method disclosed EBP-like proteins, but in much lesser concentrations, in some of the other tissues tested. The concentration of these proteins in the human and baboon prostates was much lower (average for the baboon cranial lobe 4800dpm/mg cytosol protein, with a somewhat higher value for the caudal lobe) than that in the rat gland. The amount of the EBP-like protein was higher in prostatic cancer than in that of benign prostatic hypertrophy (BPH) (range 9350 - 25,900 vs. 2200 - 18,900 dpm/mg cytosol protein). In the human, the highest value was found in one normal prostate tested (106,000 dpm/mg) cytosol protein).
Purification and characterization of aromatase from human placenta
Hall, Peter F.,Chen, Shiuan,Nakajin, Shizuo,Shinoda, Masato,Shively, John E.
, p. 37 - 50 (1987)
Amino acid sequence of these peptides reveal that histidine is the carboxy-terminal amino acid of the protein and that significant homology exists with corresponding peptides from other cytochromes P-450.Unique oligonucleotides (62 and 30 MER) synthesized on the basis of a 45 amino acid sequence near the center of the molecular have been used to clone the aromatase gene from a cDNA expresssion library from human placenta in λgt11.
An environmentally friendly and cost effective synthesis of estradiol featuring two novel reagents: Si(0)/KF and PMHS/hexamethyldisiloxane/pTSA
Lim, Chongsoo,Evenson, Gerald N.,Perrault, William R.,Pearlman, Bruce A.
, p. 6417 - 6420 (2006)
Si(0)/KF is introduced as a strong, inexpensive, environmentally friendly, and safe reagent for 'dissolving metal'-type reduction. PMHS/hexamethyldisiloxane/pTSA is introduced as an inexpensive substitute for Et3SiH/TFA for 'ionic hydrogenation', where the hexamethyldisiloxane functions as a capping agent to block the oligomeric silicone by-product from cross-linking to a gel, rubber, or plastic. An environmentally friendly and cost effective synthesis of estradiol is described which showcases these new reagents.
A COMPARISON OF THREE METHODS OF HYDROLYSIS FOR ESTROGEN CONJUGATES
Bain, J. D.,Kasman, L. H.,Bercovitz, A. B.,Lasley, B. L.
, p. 603 - 620 (1984)
The efficiencies for estrogen conjugate hydrolysis were compared between enzyme hydrolysis, acid solvolysis and a new method, ammonolysis.Samples included: 1) crystalline 1,3,5(10)-estratriene-3,17β-diol disulfate (estradiol 3,17-disulfate), 2) squirrel monkey urine collected following an intravenous injection of 1,3,5(10)-estratriene-3,17β-diol (estradiol) and 3) a pool of human pregnancy urine.Ammonolysis demonstrated a significant increase over the other techniques in "free" estrogen yields, specifically, from estradiol 3,17-disulfate.
Promiscuity of an unrelated anthrol reductase ofTalaromyces islandicusWF-38-12
Singh, Shailesh Kumar,Rajput, Anshul,De, Arijit,Chakraborti, Tapati,Husain, Syed Masood
, p. 474 - 478 (2021/02/09)
An anthrol reductase ofTalaromyces islandicusWF-38-12 (ARti-2) from an unrelated biosynthetic gene cluster (BGC) has been identified and characterized. It catalyses the NADPH-dependent reduction of anthrols (hydroanthraquinones), estrone and a naphthol with high stereo- and regioselectivity. The role of ARti-2, theCRG89872.1gene of the same BGC and non-enzymatic oxidation in the biosynthesis of (?)-flavoskyrin has been proposed.
One-Step Chemo-, Regio- and Stereoselective Reduction of Ketosteroids to Hydroxysteroids over Zr-Containing MOF-808 Metal-Organic Frameworks
Llabrés i Xamena, F. X.,Mautschke, H.-H.
, p. 10766 - 10775 (2021/06/15)
The kinetic rate constant and thermodynamic parameters of estrone reduction to estradiol have been obtained by a detailed temperature-dependent kinetic analysis. The results evidence a major contribution of the entropic term, thus suggesting that the diastereoselectivity of the process is controlled by the confinement of the reaction inside the MOF cavities, where the Zr4+ active sites are located.
Potent aromatase inhibitors through fungal transformation of anti-cancer drug testolactone: An approach towards treatment of breast cancer
-
Paragraph 0021, (2021/07/30)
It is a key target for the discovery of chemotherapeutic agents against ER+ (estrogen-positive) breast-cancers and several other diseases caused by overexpression of aromatase enzyme. Metabolites 3 (IC50=8.60±0.402 nM), and 4 (IC50=9.23±1.31 nM) were identified as potent inhibitors against human aromatase enzyme, in comparison to 1 (IC50=0.716±0.031 μM), and the standard aromatase inhibiting drug, exemestane (IC50=0.232±0.031 μM). Derivatives 2 (IC50=11.68±0.73 μM), 5 (IC50=10.37±0.50 μM) and 6 (IC50=0.82±0.059 μM) have also a good inhibition against aromatase enzyme. Therefore, metabolites 2-6 have the potential to serve as therapeutic agents against diseases caused by aromatase enzyme, including breast cancer.
Solvent- and Wavelength-Dependent Photolysis of Estrone
Adriano, Natalie,Ahearn, Ceilidh,Black, Cory,Cracchiolo, Michael,Ghere, Daniel,Hare, Patrick M.,Nu?ez, Alexandra,Olivan, Lars,Patel, Raj,Saner, Stephanie,Smith, Krista R.,Watkins, Barbie
, (2021/11/08)
The direct photolysis of estrone in solvents ranging from water to cyclohexane is reported. The photodegradation is dominated by lumiestrone, an epimer of estrone resulting from the inversion of the methyl group at carbon 13, regardless of solvent and pho
50-28-2 Process route
-
- 63-05-8
Androstenedione
-
- 50-28-2
estradiol
-
- 53-16-7
Estrone
-
- 58-22-0
testosterone
-
- 521-18-6
Stanolone
-
- 53-42-9
Etiocholanolone
-
- 53-41-8
cis-androsterone
| Conditions | Yield |
|---|---|
|
With carcinoma; gynecomastia; mammary dysplasia; at 37 ℃; for 1.5h; Product distribution; cofactors under 95percent O2: 5percent CO2, <3H>labeled study;
|
-
- 157231-19-1
17β-estradiol 3'-(saccharinylmethyl) ether
-
- 50-00-0,30525-89-4,61233-19-0
formaldehyd
-
- 50-28-2
estradiol
-
- 81-07-2
saccharin
| Conditions | Yield |
|---|---|
|
With phosphate buffer; water; In methanol; at 37 ℃; Rate constant; various pH-values (4.98-7.98); half-life; other media, other temperature;
|
50-28-2 Upstream products
-
91-22-5
quinoline
-
846-48-0
1-dehydrotestosterone
-
99-35-4
1,3,5-trinitrobenzene
-
53-16-7
Estrone
50-28-2 Downstream products
-
1474-52-8
17β-oestradiol diacetate
-
1743-60-8
17-β-estradiol 17-acetate
-
24381-12-2
2-iodo-17β-oestradiol
-
15833-07-5
2-bromo-17β-oestradiol
Relevant Products
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Thiobenzoic acidCAS NO.: 98-91-9CAS：98-91-9
-
N,N'-1,3-Phenylene bismaleimideCAS：3006-93-7
-
Estradiol valerateCAS：979-32-8
