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Merck
CN

E125

β-Estradiol

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
EC Number:
200-023-8
UNSPSC Code:
12352200
PubChem Substance ID:
329798995
Beilstein/REAXYS Number:
1914275
MDL number:
MFCD00003693

Key Documents

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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

mp

176-180 °C (lit.)

storage temp.

2-8°C

Gene Information

human ... ESR1(2099)

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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.

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

188.6 °F

flash_point_c

87 °C

ppe

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

Regulatory Information

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Hirotaka Ishii et al.
The Neuroscientist : a review journal bringing neurobiology, neurology and psychiatry, 13(4), 323-334 (2007-07-24)
It is believed that sex hormones are synthesized in the gonads and reach the brain via the blood circulation. In contrast with this view, the authors have demonstrated that sex hormones are also synthesized locally in the hippocampus and that
Mark A Tarnopolsky
Medicine and science in sports and exercise, 40(4), 648-654 (2008-03-05)
Women oxidize more lipid and less carbohydrate and protein compared with men during endurance exercise. The increase in fat oxidation is associated with higher intramyocellular lipid content and use as well as greater adipocyte lipolysis. Glucose rates of appearance and
Pascal Pigeon et al.
Journal of medicinal chemistry, 48(8), 2814-2821 (2005-04-15)
A series of ruthenocene derivatives, 1-[4-(O(CH(2))(n)()N(CH(3))(2))phenyl]-1-(4-hydroxyphenyl)-2-ruthenocenylbut-1-ene, with n = 2-5, based on the structure of the breast cancer drug tamoxifen has been prepared. These compounds were obtained, via a McMurry cross-coupling reaction, as a mixture of Z and E isomers
Michael J Gibney et al.
The American journal of clinical nutrition, 82(3), 497-503 (2005-09-13)
Metabolomics has been widely adopted in pharmacology and toxicology but is relatively new in human nutrition. The ultimate goal, to understand the effects of exogenous compounds on human metabolic regulation, is similar in all 3 fields. However, the application of
Artem Cherkasov et al.
Journal of medicinal chemistry, 49(25), 7466-7478 (2006-12-08)
A combination of protein-ligand docking and ligand-based QSAR approaches has been elaborated, aiming to speed-up the process of virtual screening. In particular, this approach utilizes docking scores generated for already processed compounds to build predictive QSAR models that, in turn
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