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Merck

E8875

Sigma-Aldrich

17β-Estradiol

≥98% (HPLC), powder, estrogenic hormone

Sinónimos:

1,3,5-Estratriene-3,17β-diol, 17β-Estradiol, 3,17β-Dihydroxy-1,3,5(10)-estratriene, Dihydrofolliculin

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About This Item

Fórmula empírica (notación de Hill):
C18H24O2
Número de CAS:
Peso molecular:
272.38
Beilstein/REAXYS Number:
1914275
EC Number:
MDL number:
UNSPSC Code:
12352104
PubChem Substance ID:
NACRES:
NA.77
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Nombre del producto

β-Estradiol, ≥98%

biological source

synthetic (organic)

Quality Level

sterility

non-sterile

assay

≥98%

form

powder

technique(s)

cell culture | mammalian: suitable

mp

176-180 °C (lit.)

solubility

ethanol: 50 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

SMILES string

O[C@H]1CC[C@@]2([H])[C@]3([H])CCC4=CC(O)=CC=C4[C@@]3([H])CC[C@@]21C

InChI

1S/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+/m1/s1

InChI key

VOXZDWNPVJITMN-ZBRFXRBCSA-N

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General description

β-Estradiolis a natural steroid estrogen[1] and a female sex hormone.[2] It is an essential component of the female menstrual cycle and plays an important role in the growth and maintenance of the reproductive system.[2]

Application

β-Estradiol has been used:
  • for the in vitro maturation of bovine cumulus-oocyte complexes (COCs)[3]
  • as a supplement in in vitro maturation medium (IVM), which is used as a control medium[4]
  • in estrogen-induction assay[5]

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.
The major estrogen secreted by the premenopausal ovary.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) and Nuclear Receptors (Steroids) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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Referencia del producto
Descripción
Precios

pictograms

Health hazardEnvironment

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Lact. - Repr. 1A

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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Three-step in vitro maturation culture of bovine oocytes imitating temporal changes of estradiol-17beta and progesterone concentrations in preovulatory follicular fluid.
Matsuo M, et al.
Archives Animal Breeding, 60(4), 385-390 (2017)
Natriuretic peptide receptor 2 (NPR2) localized in bovine oocyte underlies a unique mechanism for C-type natriuretic peptide (CNP)-induced meiotic arrest.
Xi G, et al.
Theriogenology, 106, 198-209 (2018)
Synthesis and electrochemical characterization of nanostructured magnetic molecularly imprinted polymers for 17-beta-Estradiol determination
Lahcen A, et al.
Sensors and Actuators B, Chemical, 241, 698-705 (2017)
Supra molecular mechanism of the removal of 17-beta-estradiol endocrine disturbing pollutant from water on functionalized iron nano particles
Ali I, et al.
Journal of Molecular Liquids, 241, 123-129 (2017)
Youqiang Li et al.
International journal of oncology, 46(4), 1461-1472 (2015-02-06)
Hormone therapy targeting estrogen receptor α (ERα) is the most effective treatment for breast cancer. However, this treatment eventually fails as the tumor develops resistance. Although reduced expression of ER-α is a known contributing factor to endocrine resistance, the mechanism

Questions

  1. Which of the two options, E1024 or E8875, is preferable for use as 1) an oral supplement and 2) silastic tube release? Additionally, among these which one is better for dissolving estrogen in sesame oil.

    1 answer
    1. The in vivo application is beyond the scope of product characterization efforts. However, for the specified applications, E8875 is highly recommended, as it has been well cited in the literature. The following publications may be of interest for protocol reference:

      1. J Vis Exp. 2012 Jun 7;(64):e4013. Ovariectomy and 17β-estradiol replacement in rats and mice: a visual demonstration. PMID: 22710371

      2. Am J Physiol Regul Integr Comp Physiol. 2009 Sep;297(3):R587-92. Loss of ovarian function in the VCD mouse-model of menopause leads to insulin resistance and a rapid progression into the metabolic syndrome. PMID: 19439618

      3. Eur J Pharmacol. 2021 May 25;906:174175. Apigenin acts as a partial agonist action at estrogen receptors in vivo. PMID: 34048736

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