E2257

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
• 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: 24894462
• NACRES: NA.77

Properties

• 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)

Description

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.

Safety Information

• pictograms: GHS08,GHS09
• signalword: Danger
• hcodes: H351,H360FD,H362,H410
• pcodes: P202 - P260 - P263 - P264 - P273 - P308 + P313
• 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