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E8515

Sigma-Aldrich

β-Estradiol 3-benzoate

≥97%

Synonym(s):

1,3,5(10)-Estratriene-3,17β-diol 3-benzoate, 3,17β-Dihydroxy-1,3,5(10)-estratriene 3-benzoate, 3-Benzoyloxy-17β-estrol

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About This Item

Empirical Formula (Hill Notation):
C25H28O3
CAS Number:
50-50-0
Molecular Weight:
376.49
Beilstein:
3107526
EC Number:
200-043-7
MDL number:
MFCD00003692
UNSPSC Code:
51111800
PubChem Substance ID:
24894677
NACRES:
NA.77

Assay

≥97%

mp

191-198 °C (lit.)

SMILES string

[H][C@]12CC[C@]3(C)[C@@H](O)CC[C@@]3([H])[C@]1([H])CCc4cc(OC(=O)c5ccccc5)ccc24

InChI

1S/C25H28O3/c1-25-14-13-20-19-10-8-18(28-24(27)16-5-3-2-4-6-16)15-17(19)7-9-21(20)22(25)11-12-23(25)26/h2-6,8,10,15,20-23,26H,7,9,11-14H2,1H3/t20-,21-,22+,23+,25+/m1/s1

InChI key

UYIFTLBWAOGQBI-BZDYCCQFSA-N

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Application

β-Estradiol 3-benzoate has been used:to mimic estradiol in rat during the oestrous cycle in rats. It has also been used along with progesterone for the induction of sexual receptivity in female rat.
Used in a study of general steroid metabolism and clearing, as groundwork for anabolic steroid screening in athletes.

Biochem/physiol Actions

β-Estradiol 3-benzoate is a synthetic estrogen. It favors breast cancer progression. It is an endocrine disrupting chemicals. It interacts with endocrine system and cause harmful effect on reproduction in animals and humans. It binds to estrogen receptors and favors tumor metastatis in breast, prostate and bone cells.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H351,H360FD

Hazard Classifications

Carc. 2 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Electrochemical sensing of estradiol benzoate using hydroxyapatite with three-dimensional channel frameworks
Wen Y, et al.
Analytical Methods : Advancing Methods and Applications, 9(40), 5868-5872 (2017)
Sexual behavior increases cell proliferation in the rostral migratory stream and promotes the differentiation of the new cells into neurons in the accessory olfactory bulb of female rats
Corona R, et al.
Frontiers in Neuroscience, 10, 48-48 (2016)
M A Mohr et al.
Hormones and behavior, 111, 110-113 (2018-12-16)
In females, a hallmark of puberty is the luteinizing hormone (LH) surge that triggers ovulation. Puberty initiates estrogen positive feedback onto hypothalamic circuits, which underlie the stimulation of gonadotropin releasing hormone (GnRH) neurons. In reproductively mature female rodents, both estradiol
Acupuncture does not ameliorate metabolic disturbances in the P450 aromatase inhibitor-induced rat model of polycystic ovary syndrome
Maliqueo M, et al.
Experimental Physiology, 102(1), 113-127 (2017)
Enhancing Effects of beta-Estradiol 3-Benzoate but Not Methoxychlor on the Promotion/Progression Stage of Chemically-induced Mammary Carcinogenesis in Ovariectomized Rats
Ueda M, et al.
Japanese Journal of Cancer Research, 93(7), 752-759 (2002)
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