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    Ethinyl Estradiol (Ethynylestradiol)
    Ethinyl Estradiol (Ethynylestradiol)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1735
    CAS #: 57-63-6 Purity ≥98%

    Description: Ethinyl Estradiol (Ethynylestradiol; 17α-Ethynylestradiol) is a semisynthetic estrogen which is orally bioactive and is used in almost all modern formulations of combined oral contraceptive pills. It is a synthetic analog of estradiol commonly used as an oral contraceptive, often in combination with a progestin. Efficacy of oral administration is facilitated by the ethynyl substitution at the C-17 position, which inhibits first pass hepatic metabolism. It is rapidly absorbed from gastrointestinal tract.

    References: Toxicol Sci. 1999;51(2):224-35; Toxicol Sci. 2003;75(2):271-8. 2003; Toxicol Sci. 2010;114(1):133-48. 

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    Molecular Weight (MW)296.4 
    FormulaC20H24O2 
    CAS No.57-63-6 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 59 mg/mL (199.1 mM) 
    Water: <1 mg/mL
    Ethanol: 59 mg/mL (199.1 mM) 
    Other info

    Chemical Name: (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

    InChi Key: BFPYWIDHMRZLRN-SLHNCBLASA-N

    InChi Code: 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 Code: C[[email protected]]12CC[[email protected]]3[[email protected]]([[email protected]@H]1CC[[email protected]]2(C#C)O)CCC4=C3C=CC(=C4)O

    Synonyms

    Ethinyloestradiol; Ethynyl estradiol; Ginestrene; Ethinyl Estradiol; Ethynylestradiol; Microfollin Forte; Organon; Progynon C


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    In Vitro

    In vitro activity: 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.

    In VivoEthinyl 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.  
    Animal modelRats
    Formulation & Dosage50 mg/kg
    References

    Toxicol Sci. 1999 Oct;51(2):224-35; Toxicol Sci. 2003 Oct;75(2):271-8. Epub 2003 Jul 11; Toxicol Sci. 2010 Mar;114(1):133-48.  


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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