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Merck

E8875

17β-Estradiol

≥98% (HPLC), powder, estrogenic hormone

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
NACRES:
NA.77
PubChem Substance ID:
24278426
UNSPSC Code:
12352104
EC Number:
200-023-8
MDL number:
MFCD00003693
Beilstein/REAXYS Number:
1914275

Product Name

β-Estradiol, ≥98%

InChI key

VOXZDWNPVJITMN-ZBRFXRBCSA-N

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

SMILES string

O[C@H]1CC[C@@]2([H])[C@]3([H])CCC4=CC(O)=CC=C4[C@@]3([H])CC[C@@]21C

biological source

synthetic (organic)

sterility

non-sterile

assay

≥98%

form

powder

technique(s)

cell culture | mammalian: suitable

mp

176-180 °C (lit.)

solubility

ethanol: 50 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

Quality Level

300

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

Biochem/physiol Actions

The major estrogen secreted by the premenopausal ovary.
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.

General description

β-Estradiolis a natural steroid estrogen and a female sex hormone. It is an essential component of the female menstrual cycle and plays an important role in the growth and maintenance of the reproductive system.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000521033
0000521033
0000519728
0000519728
0000468509

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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)
Synthesis and electrochemical characterization of nanostructured magnetic molecularly imprinted polymers for 17-beta-Estradiol determination
Lahcen A, et al.
Sensors and Actuators B, Chemical, 241, 698-705 (2017)
Supra molecular mechanism of the removal of 17-beta-estradiol endocrine disturbing pollutant from water on functionalized iron nano particles
Ali I, et al.
Journal of Molecular Liquids, 241, 123-129 (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)
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
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