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Merck

E4876

17α-Ethynylestradiol

≥98%, Synthetic estrogen, powder

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

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About This Item

Empirical Formula (Hill Notation):
C20H24O2
CAS Number:
57-63-6
Molecular Weight:
296.40
NACRES:
NA.77
PubChem Substance ID:
24894585
UNSPSC Code:
12352200
EC Number:
200-342-2
MDL number:
MFCD00003690
Beilstein/REAXYS Number:
2419975
Assay:
≥98%
Form:
powder

Key Documents

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Product Name

17α-Ethynylestradiol, ≥98%

biological source

synthetic

InChI key

BFPYWIDHMRZLRN-SLHNCBLASA-N

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

SMILES string

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

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

Gene Information

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

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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.

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).

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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

WGK 3

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

E4876-VAR: + E4876-10G: + E4876-1G: + E4876-BULK: + E4876-100MG:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5444V
WXBF4256V
WXBF0210V
WXBD7515V
WXBD9304V

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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)
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
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)
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