Skip to Content
MilliporeSigma
All Photos(3)

Documents

E4876

Sigma-Aldrich

17α-Ethynylestradiol

≥98%

Synonym(s):

17α-Ethynyl-1,3,5(10)-estratriene-3,17β-diol, 19-Nor-1,3,5(10),17α-pregnatrien-20-yne-3,17-diol, Ethinylestradiol

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C20H24O2
CAS Number:
57-63-6
Molecular Weight:
296.40
Beilstein/REAXYS Number:
2419975
EC Number:
200-342-2
MDL number:
MFCD00003690
UNSPSC Code:
12352200
PubChem Substance ID:
24894585
NACRES:
NA.77

biological source

synthetic

sterility

non-sterile

assay

≥98%

form

powder

mp

182-183 °C (lit.)

solubility

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

shipped in

ambient

storage temp.

room temp

SMILES string

[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

InChI key

BFPYWIDHMRZLRN-SLHNCBLASA-N

Gene Information

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

Looking for similar products? Visit Product Comparison Guide

General description

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.

Biochem/physiol Actions

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

ppe

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Purification of low density lipoprotein receptor from liver and its quantification by anti-receptor monoclonal antibodies
Gherardi E, et al.
The Biochemical Journal, 253(2), 409-415 (1988)
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)
Occurrence of 17alpha-ethynylestradiol (EE2) in the environment and effect on exposed biota: a review
Aris AZ, et al.
Environment International, 69, 104-119 (2014)
Ovariectomized rats as a model of postmenopausal osteoarthritis: validation and application
Hoegh-Andersen P, et al.
Arthritis Research & Therapy, 6(2), R169-R169 (2004)
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service