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E2758 Sigma-Aldrich

β-Estradiol

BioReagent, powder, 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 24894483

  •  NACRES NA.77

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Properties

Related Categories Cell Biology, Cell Culture, Cell Signaling and Neuroscience, Cytokines, Growth Factors and Hormones, Estrogen,
Quality Level   200
biological source   synthetic (organic)
product line   BioReagent
assay   ≥98% (HPLC)
form   powder
application(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
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 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.

Application

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

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

Packaging

1, 5 g in glass bottle

250 mg in glass bottle

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.

Physical form

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

Reconstitution

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
KG2975000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

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Peer-Reviewed Papers
15

References

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