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E2257

Sigma-Aldrich

β-Estradiol

powder, γ-irradiated, 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:
1914275
EC Number:
200-023-8
MDL number:
MFCD00003693
UNSPSC Code:
12352209
PubChem Substance ID:
24894462
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

sterility

γ-irradiated

product line

BioXtra

Assay

≥98% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

mp

176-180 °C (lit.)

solubility

ethanol: 1 mg/mL, clear, colorless to very faintly yellow

suitability

suitable for

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

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H351,H360FD,H362,H410

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

Regulatory Information

监管及禁止进口产品

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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Improving in vitro maturation and pregnancy outcome in cattle using a novel oocyte shipping and maturation system not requiring a CO2 gas phase
Barcelo-Fimbres M, et al.
Theriogenology, 84(1), 109-117 (2015)
Estrogen preserves Fas ligand levels by inhibiting microRNA-181a in bone marrow-derived mesenchymal stem cells to maintain bone remodeling balance
Shao B, et al.
Faseb Journal, 29(9), 3935-3944 (2015)
Determination of 17 beta-estradiol in pharmaceutical preparation by UV spectrophotometry and high performance liquid chromatography methods
Yilmaz B and Kadioglu Y
Arabian Journal of Chemistry, 10, S1422-S1428 (2017)
DHEA improves the antioxidant capacity of endometrial stromal cells and improves endometrium receptivity via androgen receptor
Qin A, et al.
Eur. J. Obstet. Gyn. Rep. Biol., 198, 120-126 (2016)
Samantha L P Schilit et al.
American journal of human genetics, 106(1), 41-57 (2019-12-24)
Unexplained infertility affects 2%-3% of reproductive-aged couples. One approach to identifying genes involved in infertility is to study subjects with this clinical phenotype and a de novo balanced chromosomal aberration (BCA). While BCAs may reduce fertility by production of unbalanced
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