| Identification | More | [Name]
Estradiol | [CAS]
50-28-2 | [Synonyms]
17BETA-ESTRADIOL-16,16,17-D3
BETA-ESTRADIOL-16,16,17-D3
(+)-3,17β-estradiol
(17b)-estra-1,3,5(10)-triene-3,17diol
(17β)-estra-1,3,5(10)-triene-3,17diol
.alpha.-Oestradiol
.beta.-Oestradiol
17-.beta.-Estra-1,3,5(10)-triene-3,17-diol
17-.beta.-Oestra-1,3,5(10)-triene-3,17-diol
17-beta-estra-1,3,5(10)-triene-3,17-diol
17beta-Estra-1,3,5(10)-triene-3,17-diol
17-beta-oestra-1,3,5(10)-triene-3,17-diol
17beta-Oestra-1,3,5(10)-triene-3,17-diol
17-beta-oh-estradiol
17beta-OH-estradiol
17-beta-oh-oestradiol
17beta-OH-oestradiol
17β-estradiol
3,17-.beta.-Dihydroxy-1,3,5(10)-oestratriene
3,17-.beta.-Dihydroxyestra-1,3,5(10)-triene | [EINECS(EC#)]
200-023-8 | [Molecular Formula]
C18H24O2 | [MDL Number]
MFCD01074033 | [Molecular Weight]
272.38 | [MOL File]
50-28-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Estradiol, 17-β-is an odorless white to yellow
crystalline substance. | [Melting point ]
178-179 °C(lit.)
| [alpha ]
D25 +76 to +83° (dioxane) | [Boiling point ]
355.44°C (rough estimate) | [density ]
1.0708 (rough estimate) | [refractive index ]
80.4 ° (C=1, Dioxane) | [Fp ]
2℃ | [storage temp. ]
2-8°C | [solubility ]
Practically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent), slightly soluble in methylene chloride. | [form ]
powder
| [pka]
pKa 10.71±0.02(H2O(0.1% p-dioxane) t=25±0.1 I=0.03(KCl))(Approximate) | [color ]
White to off-white | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
Soluble in dimethyl sulfoxide, ethanol , water, phosphate buffer saline, dimethyl formamide, acetone, dioxane and alkali hydroxides. Slightly soluble in vegetable oils. | [Usage]
Potent mammalian estrogenic hormone produced by the ovary. | [Merck ]
14,3703 | [BRN ]
1914275 | [BCS Class]
1 | [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. | [InChIKey]
VOXZDWNPVJITMN-ZBRFXRBCSA-N | [CAS DataBase Reference]
50-28-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Estra-1,3,5(10)-triene-3,17beta-diol(50-28-2) | [EPA Substance Registry System]
50-28-2(EPA Substance) |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Powder | [Uses]
Estradiol is the major estrogen secreted by the premenopausal ovary. | [Uses]
Potent mammalian estrogenic hormone produced by the ovary. | [Definition]
ChEBI: The 17beta-isomer of estradiol. | [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. | [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 | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit | [Shipping]
UN3249 Medicine, solid, toxic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials | [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 medium
in estrogen-induction assay | [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). | [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). | [Synthesis]
Estradiol, estra-1,3,5(10)-trien-3,17|?-diol (28.1.17), is most easily made by
reducing the keto-group of estrone by various reducing agents, in particular potassium
borohydride.
| [storage]
Store at RT | [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.] |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R60:May impair fertility.
R61:May cause harm to the unborn child.
R45:May cause cancer.
R63:Possible risk of harm to the unborn child. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S22:Do not breathe dust .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
2811 | [WGK Germany ]
3
| [RTECS ]
KG2975000
| [F ]
8-10 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29372300 | [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. | [Hazardous Substances Data]
50-28-2(Hazardous Substances Data) | [Toxicity]
LD50 subcutaneous in rat: > 300mg/kg |
|
|