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E2758

Sigma-Aldrich

β-Estradiol

BioReagent, powder, suitable for cell culture

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C18H24O2
Numero CAS:
Peso molecolare:
272.38
Beilstein:
1914275
Numero CE:
Numero MDL:
Codice UNSPSC:
12352209
ID PubChem:
NACRES:
NA.77

Origine biologica

synthetic (organic)

Livello qualitativo

Nome Commerciale

BioReagent

Saggio

≥98% (HPLC)

Stato

powder

tecniche

cell culture | mammalian: suitable
single cell analysis: suitable

Punto di fusione

176-180 °C (lit.)

Solubilità

ethanol: 50 mg/mL, clear, colorless

Condizioni di spedizione

ambient

Temperatura di conservazione

room temp

Stringa SMILE

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
VOXZDWNPVJITMN-ZBRFXRBCSA-N

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Descrizione generale

β-Estradiol or estradiol-17 β (E2) is secreted majorly by the large preovulatory follicles in the ovary. In addition, estradiol can be synthesized de novo from cholesterol have androgens synthesized from cholesterol. The aromatization of androgen by enzyme aromatase (P450arom) results in the β-estradiol production.

Applicazioni

β-Estradiol has been used:
  • as a component of Dulbecco′s modified Eagle medium (DMEM) for culturing mammary tumor cells
  • as a oestrogenic compound for testing neuroprotective effects
  • as a component of medium199 for culturing oocytes

β-Estradiol is used to study cell differentiation and transformations (tumorigenicity).

Azioni biochim/fisiol

β-Estradiol (E2) is a major premenopausal hormone in women and is essential for spermiogenesis, sperm maturation and motility in men. Cultured bone marrow stem cells (BMSCs) have ability to synthesize E2 and could be exploited for treating estrogen deficiency. It mediates physiological functions through estrogen receptor (ER) α and ERβ.
The major estrogen secreted by the premenopausal ovary.
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.

Stato fisico

powder-RT; stock-frozen in working aliquots, avoid repeated freeze/thaw

Ricostituzione

To prepare a 20 μg/ml stock solution, add 1 ml absolute ethanol to 1 mg β-estradiol; gently swirl to dissolve; add 49 ml sterile medium while mixing.

Pittogrammi

Health hazardEnvironment

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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


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Loss of STAT1 from mouse mammary epithelium results in an increased Neu-induced tumor burden
Klover PJ, et al.
Neoplasia, 12(11), 899-905 (2010)
The developmental potential of oocytes is impaired in cattle with liver abnormalities
Sarentonglaga B, et al.
Journal of Reproduction and Development, 59(2), 168-173 (2013)
Estradiol synthesis and release in cultured female rat bone marrow stem cells
Zhang D, et al.
BioMed Research International, 2013 (2013)
Molecular mechanism of estrogen-estrogen receptor signaling
Yacsar P, et al.
Reproductive medicine and biology, 16(1), 4-20 (2017)
Estrogen synthesis and signaling pathways during aging: from periphery to brain
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