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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

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About This Item

Empirical Formula (Hill Notation):
C18H24O2
CAS Number:
50-28-2
Molecular Weight:
272.38
Beilstein/REAXYS Number:
1914275
EC Number:
200-023-8
MDL number:
MFCD00003693
UNSPSC Code:
12352209
PubChem Substance ID:
24894483
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

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

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)

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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.

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
GHS08,GHS09

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Molecular mechanism of estrogen-estrogen receptor signaling
Yacsar P, et al.
Reproductive medicine and biology, 16(1), 4-20 (2017)
Estrogen synthesis and signaling pathways during aging: from periphery to brain
Cui J, et al.
Trends in Molecular Medicine, 19(3), 197-209 (2013)
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