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E2257 Sigma-Aldrich

β-Estradiol

powder, γ-irradiated, suitable for cell culture

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

  • CAS Number 50-28-2

  • Empirical Formula (Hill Notation) C18H24O2

  • Molecular Weight 272.38

  •  Beilstein/REAXYS Number 1914275

  •  EC Number 200-023-8

  •  MDL number MFCD00003693

  •  PubChem Substance ID 24894462

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Properties

Related Categories Cell Biology, Cell Culture, Cell Signaling and Neuroscience, Cytokines, Growth Factors and Hormones, Estrogen,
Quality Level   200
sterility   γ-irradiated
form   powder
application(s)   cell culture | mammalian: suitable
mp   176-180 °C (lit.)
suitability   suitable for
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
Gene Information   human ... ESR1(2099), ESR2(2100), ESRRA(2101), ESRRB(2103), GPER(2852), SERPINA6(866)
mouse ... Esr1(13982), Esr2(13983), Esrra(26379)
rat ... Afp(24177), Ar(24208), Esr1(24890), Esr2(25149), Shbg(24775)

Description

General description

β-estradiol is a natural human estrogen. It is important for the growth of breast and reproductive epithelia, maturation of long bones and the development of secondary sexual characteristics. Estradiol is produced by immature germ cells, spermatozoa, Leydig cells and Sertoli cells. It plays a crucial role in proliferation, regulation of ion transport and regulation of apoptosis in Sertoli cells. Estradiol regulates sperm concentration, motility and morphology. β-estradiol functions as a menopausal hormone. It is implicated in replacement therapy for female hypogonadism or primary ovarian failure. Reduced levels of β-estradiol are associated with heart disease and osteoporosis.

Application

β-estradiol has been used:
• for primary culture of mouse endometrial stromal cells (ESCs)
• for estrogen treatment in vitro
• in the in vitro maturation of cumulus–oocyte complexes (COCs)

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.

Physical form

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

Reconstitution

To prepare 20 μg/ml stock solution: add 1 ml absolute ethanol; gently swirl to dissolve; add 49 ml sterile medium while mixing.

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
KG2975000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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