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E2758

Sigma-Aldrich

β-Estradiol

BioReagent, powder, suitable for cell culture

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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)

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

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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This Item
E2257E8875E1132
β-Estradiol BioReagent, powder, suitable for cell culture

Sigma-Aldrich

E2758

β-Estradiol

β-Estradiol powder, γ-irradiated, suitable for cell culture

Sigma-Aldrich

E2257

β-Estradiol

β-Estradiol ≥98%

Sigma-Aldrich

E8875

β-Estradiol

β-Estradiol analytical standard

Sigma-Aldrich

E1132

β-Estradiol

product line

BioReagent

product line

BioXtra

product line

-

product line

-

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98%

assay

-

form

powder

form

powder

form

powder

form

-

technique(s)

cell culture | mammalian: suitable, single cell analysis: suitable

technique(s)

cell culture | mammalian: suitable

technique(s)

cell culture | mammalian: suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

mp

176-180 °C (lit.)

mp

176-180 °C (lit.)

mp

176-180 °C (lit.)

mp

176-180 °C (lit.)

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 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).

Biochem/physiol Actions

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. 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 Acute 1 - 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

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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)
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)
Estrogen synthesis and signaling pathways during aging: from periphery to brain
Cui J, et al.
Trends in Molecular Medicine, 19(3), 197-209 (2013)
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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