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Merck

E2758

β-Estradiol

BioReagent, powder, suitable for cell culture

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 CAS:
Peso molecular:
272.38
UNSPSC Code:
12352209
NACRES:
NA.77
PubChem Substance ID:
EC Number:
200-023-8
Beilstein/REAXYS Number:
1914275
MDL number:
biological source:
synthetic (organic)
form:
powder
assay:
≥98% (HPLC)

Nombre del producto

β-Estradiol, BioReagent, powder, suitable for cell culture

InChI key

VOXZDWNPVJITMN-ZBRFXRBCSA-N

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

SMILES string

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

biological source

synthetic (organic)

product line

BioReagent

assay

≥98% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable
single cell analysis: suitable

mp

176-180 °C (lit.)

solubility

ethanol: 50 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

Quality Level

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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.
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.

Application

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).

General description

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.

Physical form

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

Preparation Note

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.

pictograms

Health hazardEnvironment

signalword

Danger

Hazard Classifications

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

Clase de almacenamiento

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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Visite la Librería de documentos

Estradiol synthesis and release in cultured female rat bone marrow stem cells
Zhang D, et al.
BioMed Research International, 2013 (2013)
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)
Estrogen synthesis and signaling pathways during aging: from periphery to brain
Cui J, et al.
Trends in Molecular Medicine, 19(3), 197-209 (2013)
Selective oestrogen receptor (ER) modulators reduce microglia reactivity in vivo after peripheral inflammation: potential role of microglial ERs
Tapia-Gonzalez S, et al.
The Journal of Endocrinology, 198, 219?230-219?230 (2008)
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)

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