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E2758

Sigma-Aldrich

β-Estradiol

BioReagent, powder, suitable for cell culture

Synonym(s):
1,3,5-Estratriene-3,17β-diol, 17β-Estradiol, 3,17β-Dihydroxy-1,3,5(10)-estratriene, Dihydrofolliculin
Empirical Formula (Hill Notation):
C18H24O2
CAS Number:
Molecular Weight:
272.38
Beilstein:
1914275
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

product line

BioReagent

assay

≥98% (HPLC)

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-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.[37]

Application

β-Estradiol has been used:
  • as a component of Dulbecco′s modified Eagle medium (DMEM) for culturing mammary tumor cells
[40]
  • as a oestrogenic compound for testing neuroprotective effects
  • [41]
  • as a component of medium199 for culturing oocytes
  • [42]
    β-Estradiol is used to study cell differentiation and transformations (tumorigenicity).

    Packaging

    250 mg in glass bottle
    1, 5 g in glass bottle

    Biochem/physiol Actions

    β-Estradiol (E2) is a major premenopausal hormone in women and is essential for spermiogenesis, sperm maturation and motility in men.[38] Cultured bone marrow stem cells (BMSCs) have ability to synthesize E2 and could be exploited for treating estrogen deficiency.[37] It mediates physiological functions through estrogen receptor (ER) α and ERβ.[39]
    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 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

    Signal Word

    Danger

    Hazard Classifications

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

    Storage Class Code

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

    WGK

    WGK 3

    Flash Point(F)

    Not applicable

    Flash Point(C)

    Not applicable

    Personal Protective Equipment

    dust mask type N95 (US), Eyeshields, Gloves

    Certificate of Analysis

    Enter Lot Number to search for Certificate of Analysis (COA).

    Certificate of Origin

    Enter Lot Number to search for Certificate of Origin (COO).

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