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50-28-2

50-28-2 Structure

50-28-2 Structure
IdentificationMore
[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 PropertiesBack Directory
[Appearance]

Estradiol, 17-β-is an odorless white to yellow crystalline substance.
[Appearance]

White Crystalline Powder
[Melting point ]

178-179 °C(lit.)
[mp ]

178-179 °C(lit.)
[Boiling point ]

355.44°C (rough estimate)
[alpha ]

D25 +76 to +83° (dioxane)
[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
[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 AnswerBack Directory
[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.
[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 InformationBack Directory
[Chemical Properties]

White Crystalline Powder
[Uses]

Potent mammalian estrogenic hormone produced by the ovary.
[Uses]

Estradiol is the major estrogen secreted by the premenopausal 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
[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).
[Chemical 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.

[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 DataBack 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
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Nitrogen-->p-Toluenesulfonic acid-->Lithium-->Potassium borohydride-->Biphenyl-->Acetylacetone-->1,3,5(10)-Estratrien-3-ol-17-one-->Diphenylmethane-->4-ETHYL-2-METHYLPYRIDINE-->ADD
【Preparation Products】

Depofemin-->2-HYDROXYESTRADIOL-->Estramustine-->Promestriene
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

1,3,5-Estratriene-3,17beta-diol(50-28-2).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Estradiol(50-28-2) IR1
Estradiol(50-28-2) IR2
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

beta-Estradiol, 99% (dry wt.), ca 3% water(50-28-2)
[Sigma Aldrich]

50-28-2(sigmaaldrich)
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