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    Diethylstilbestrol (Stilbestrol)
    Diethylstilbestrol (Stilbestrol)

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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 #: V1732
    CAS #: 56-53-1Purity ≥98%

    Description: Diethylstilbestrol (also called Stilbestrol; DES; Distilbene) is a synthetic non-steroidal form of estrogen that can be used to prevent miscarriage and other pregnancy complications as well as in the treatment of menopausal and postmenopausal disorders. Diethylstilbestrol is a well-known teratogen and carcinogen, that inhibits the hypothalamic-pituitary-gonadal axis, thereby blocking the testicular synthesis of testosterone, lowering plasma testosterone, and inducing a chemical castration. Diethylstilbestrol promotes coactivator release from orphan nuclear receptor ERR beta and inhibits its transcriptional activity in trophoblast stem cells.

    References: Genes Dev. 2001 Apr 1;15(7):833-8; Mol Carcinog. 2003 Oct;38(2):78-84.

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    Molecular Weight (MW)268.35 
    FormulaC18H20O2 
    CAS No.56-53-1 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 54 mg/mL (201.2 mM)
    Water: <1 mg/mL
    Ethanol: 54 mg/mL (201.2 mM)
    Other info

    Chemical Name: 4-[(E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

    InChi Key: RGLYKWWBQGJZGM-ISLYRVAYSA-N

    InChi Code: InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

    SMILES Code: CC/C(=C(/CC)\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)O

    SynonymsStilbestrol; DES; Stilboestrol; Distilbene;


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    In Vitro

    In vitro activity: Diethylstilbestrol promotes coactivator release from orphan nuclear receptor ERR beta and inhibits its transcriptional activity in trophoblast stem cells.

    In VivoDiethylstilbestrol treated pregnant mice exhibits abnormal early placenta development associated with an overabundance of trophoblast giant cells and an absence of diploid trophoblast. Diethylstilbestrol causes epigenetic methylation changes that result in persistent alterations in gene expression, leading to tumorigenesis in mouse uterus. Diethylstilbestrol induces c-fos exon-4 hypomethylation at postnatal day 17 in mice uterus, while elevating its mRNA level from postnatal day 5. Diethylstilbestrol exposure leads to hypomethylation in the exon-4 region of c-fos mRNA. Diethylstilbestrol-treated rats exhibits more pronounced delay in maturational development of an adult pattern of immunoexpression of the three proteins compared with GnRHa-treated rats. Diethylstilbestrol results in similar reductions in both Sertoli cell numbers and suppression of testicular growth at 18 and 25 days, though by 35 days the suppression is more pronounced in DES-treated rats. Diethylstilbestrol treatment appears to imprint an abnormal, site-specific demethylation of CpG/-464, which requires ovarian hormones to occur in adult mice. Diethylstilbestrol (2.0 ng/g) per day increases adult prostate weight, whereas a 200 ng/g dose decreases adult prostate weight in male offspring mice. 
    Animal modelMice
    Formulation & Dosage2.0 ng/g
    References

    Genes Dev. 2001 Apr 1;15(7):833-8; Mol Carcinog. 2003 Oct;38(2):78-84.  


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

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