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E4876

Sigma-Aldrich

17α-Ethynylestradiol

≥98%

Synonyme(s) :

Ethinylestradiol

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About This Item

Formule empirique (notation de Hill):
C20H24O2
Numéro CAS:
57-63-6
Poids moléculaire :
296.40
Numéro Beilstein :
2419975
Numéro CE :
200-342-2
Numéro MDL:
MFCD00003690
Code UNSPSC :
12352200
ID de substance PubChem :
24894585
Nomenclature NACRES :
NA.77

Source biologique

synthetic

Stérilité

non-sterile

Pureté

≥98%

Forme

powder

Pf

182-183 °C (lit.)

Solubilité

ethanol: 50 mg/mL, clear, colorless to faintly yellow

Conditions d'expédition

ambient

Température de stockage

room temp

Chaîne SMILES 

[H][C@]12CC[C@@]3(C)[C@@]([H])(CC[C@@]3(O)C#C)[C@]1([H])CCc4cc(O)ccc24

InChI

1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1

Clé InChI

BFPYWIDHMRZLRN-SLHNCBLASA-N

Informations sur le gène

human ... ESR1(2099)
rat ... Afp(24177) , Esr1(24890) , Shbg(24775)

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Description générale

17α-Ethynylestradiol (EE2) is a synthetic hormone. It is a derivative of estradiol (E2). It is implicated in estrogen replacement therapy and suspension of breastfeeding. EE2 is used to treat osteoporosis, menopausal and postmenopausal syndrome. It is also used to treat prostatic cancer and breast cancer in postmenopausal women. EE2 functions as an endocrine-disrupting chemical (EDC).

Application

17α-Ethynylestradiol has been used to study the effect of exogenous estrogen and selective estrogen receptor modulator (SERM) in rats. It also has been used to increase the concentration of low density lipoprotein (LDL) receptor in rabbit liver.

Actions biochimiques/physiologiques

17α-Ethynylestradiol is an orally bio-active synthetic estrogen used as an oral contraceptive.

Pictogrammes

Health hazardExclamation markEnvironment
GHS08,GHS07,GHS09

Mention d'avertissement

Danger

Mentions de danger

H302,H351,H360Fd,H410

Classification des risques

Acute Tox. 4 Oral - Aquatic Chronic 1 - Carc. 2 - Repr. 1A

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

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Consulter la Bibliothèque de documents

Huda Omar Ali et al.
PloS one, 11(3), e0152114-e0152114 (2016-03-22)
Oestrogens influence the pathology and development of hormone-sensitive breast cancers. Tissue factor pathway inhibitor (TFPI) has been shown to be associated with breast cancer pathogenesis. Recently, we found TFPI mRNA levels to be significantly reduced by oestrogens in a breast
Richard Mark Evans et al.
PloS one, 7(8), e43606-e43606 (2012-08-23)
A growing body of experimental evidence indicates that the in vitro effects of mixtures of estrogenic chemicals can be well predicted from the estrogenicity of their components by the concentration addition (CA) concept. However, some studies have observed small deviations
Admane H Shanthanagouda et al.
PloS one, 9(2), e88165-e88165 (2014-02-14)
In human, a reduction in estrogen has been proposed as one of the key contributing factors for postmenopausal osteoporosis. Rodents are conventional models for studying postmenopausal osteoporosis, but the major limitation is that ovariectomy is needed to mimic the estrogen
Analysis of 17-beta-estradiol and 17-alpha-ethinylestradiol in biological and environmental matrices?a review
Barreiros L, et al.
Microchemical Journal, Devoted to the Application of Microtechniques in All Branches of Science, 126, 243-262 (2016)
Anders E A Dahm et al.
BMC cardiovascular disorders, 6, 40-40 (2006-10-13)
Hormone therapy, oral contraceptives, and tamoxifen increase the risk of thrombotic disease. These compounds also reduce plasma content of tissue factor pathway inhibitor-1 (TFPI), which is the physiological inhibitor of the tissue factor pathway of coagulation. The current aim was
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