E8875

Sigma-Aldrich

β-Estradiol

≥98%

Synonym(s):
17β-Estradiol, 3,17β-Dihydroxy-1,3,5(10)-estratriene, 1,3,5-Estratriene-3,17β-diol, Dihydrofolliculin
Empirical Formula (Hill Notation):
C18H24O2
CAS Number:
Molecular Weight:
272.38
Beilstein/REAXYS Number:
1914275
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

biological source

synthetic (organic)

sterility

non-sterile

assay

≥98%

form

powder

application(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

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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Application

β-Estradiol has been used:
  • for the in vitro maturation of bovine cumulus-oocyte complexes (COCs)
  • as a supplement in in vitro maturation medium (IVM), which is used as a control medium
  • in estrogen-induction assay

Packaging

250 mg in glass bottle
1, 5, 25, 100 g in glass bottle

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.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) and Nuclear Receptors (Steroids) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E8875.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Health hazardEnvironment

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Three-step in vitro maturation culture of bovine oocytes imitating temporal changes of estradiol-17beta and progesterone concentrations in preovulatory follicular fluid.
Matsuo M, et al.
Archives Animal Breeding, 60(4), 385-390 (2017)
Natriuretic peptide receptor 2 (NPR2) localized in bovine oocyte underlies a unique mechanism for C-type natriuretic peptide (CNP)-induced meiotic arrest.
Xi G, et al.
Theriogenology, 106, 198-209 (2018)
Youqiang Li et al.
International journal of oncology, 46(4), 1461-1472 (2015-02-06)
Hormone therapy targeting estrogen receptor α (ERα) is the most effective treatment for breast cancer. However, this treatment eventually fails as the tumor develops resistance. Although reduced expression of ER-α is a known contributing factor to endocrine resistance, the mechanism...
X Xue et al.
Oncogene, 35(21), 2746-2755 (2015-09-15)
Tamoxifen, an estrogen receptor (ER) antagonist, is the mainstay treatment of breast cancer and the development of resistance represents a major obstacle for a cure. Although long non-coding RNAs such as HOTAIR have been implicated in breast tumorigenesis, their roles...
Yohan Choi et al.
Biology of reproduction, 81(6), 1122-1130 (2009-07-31)
Calcium ions have been implicated in the establishment and maintenance of pregnancy, but the regulatory mechanisms of calcium ions in the uterine endometrium and conceptus are not well understood in pigs. Recently, we showed that TRPV6, a calcium ion channel...

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