Ethynyl estradiol

SKU: orb1308659

Description

Ethynyl estradiol is a synthetic estrogen derived from estradiol, featuring a 17α-ethinyl group that confers high oral bioavailability. It is a key component in oral contraceptives and is widely used in endocrine research for studying estrogen receptor signaling in both cellular and animal models.

Research Area

Metabolism Research, Pharmacology & Drug Discovery

Key Properties

• CAS Number: 57-63-6
• MW: 296.40
• Purity: >99.99% (May vary between batches)
• Formula: C₂₀H₂₄O₂
• SMILES: C[C@@]12[C@]([C@]3([C@](CC1)(C=4C(CC3)=CC(O)=CC4)[H])[H])(CC[C@]2(C#C)O)[H]
• Target: Estrogen Receptor/ERR,Endogenous Metabolite,Estrogen/progestogen Receptor
• Solubility: Ethanol:55 mg/mL (185.56 mM);DMSO:120 mg/mL (404.86 mM);10% DMSO+40% PEG300+5% Tween-80+45% Saline:3.3 mg/mL (11.13 mM)

Bioactivity

• In Vivo:
  Ethinyl Estradiol (50 mg/kg/day) increases anogenital distance and reduces pup body weight at postnatal day 2, accelerates the age at vaginal opening, reduces F1 fertility and F2 litter sizes, and induces malformations of the external genitalia (5 mg/kg) in the female Long-Evans rat. Ethinyl Estradiol increases the number of low density lipoprotein (LDL) receptors in livers of rats, thereby producing a profound fall in plasma cholesterol levels. Ethinyl Estradiol exerts the same effect in livers of male and female rabbits and that the increase in receptor number is correlated with a 6- to 8-fold increase in the levels of receptor mRNA.
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• In Vitro:
  Ethinyl Estradiol increases respiratory chain activity in both cultured rat hepatocytesand HepG2 cells. Ethinyl estradiol is a strong promoter of hepatocarcinogenesis. Ethinyl Estradiol enhances the transcript levels of nuclear genome- and mitochondrial genome-encoded genes and respiratory chain activity in female rat liver, and also inhibits transforming growth factor beta (TGFbeta)-induced apoptosis in cultured liver slices and hepatocytes from female rats. Ethinyl Estradiol increases the transcript levels of the mitochondrial genome-encoded genes cytochrome oxidase subunits I, II, and III in cultured female rathepatocytes. Ethinyl Estradiol significantly increases both the levels of glutathione (reduced [GSH] and oxidized [GSSG] forms) per mg protein in mitochondria and nuclei, while the percentage of total glutathione in the oxidized form is not affected.
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Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

EndogenousMetabolite, Endogenous Metabolite, 17a-Ethynylestradiol, 17alpha-Ethynylestradiol, 17α-Ethynylestradiol, Estrogen Receptor, Ethinyl Estradiol, Estrogen Receptor/ERR, EstrogenReceptor, ER, Ethynylestradiol, Ethynyl estradiol, ERR, inhibit, Inhibitor, progestogen Receptor, progestogenReceptor

Compound Identifiers

PubChem CID

5991