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D4628

Sigma-Aldrich

Diethylstilbestrol

≥99% (HPLC)

Synonym(e):

(E)-3,4-Bis-(4-hydroxyphenyl)-3-hexen, DES, Stilboestrol

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About This Item

Empirische Formel (Hill-System):
C18H20O2
CAS-Nummer:
56-53-1
Molekulargewicht:
268.35
Beilstein:
2056095
EG-Nummer:
200-278-5
MDL-Nummer:
MFCD00002373
UNSPSC-Code:
51111800
PubChem Substanz-ID:
24893887
NACRES:
NA.77

Assay

≥99% (HPLC)

Form

powder

SMILES String

CC\C(c1ccc(O)cc1)=C(\CC)c2ccc(O)cc2

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+

InChIKey

RGLYKWWBQGJZGM-ISLYRVAYSA-N

Angaben zum Gen

human ... ESR1(2099) , ESR2(2100) , ESRRG(2104)
mouse ... Esr1(13982)
rat ... Ar(24208) , Esr1(24890)

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Verwandte Kategorien

Anwendung

Diethylstilbestrol has been used:
  • to evaluate the estrogenic activity of diethylstilbestrol by quantitating the expression levels of endogenous estrogen-regulated marker genes
  • to evaluate the estrogenic, androgenic and toxicity responses in bioluminescent yeast bioreporter assay (BLYES)
  • to detect its effect on the proliferation and tyrosinase activity of melanocytes

Biochem./physiol. Wirkung

Diethylstilbestrol is a synthetic estrogen with carcinogenic properties. Causes renal clear-cell carcinoma in Syrian hamster. In humans it causes increased risk of breast cancer, clear cell adenocarcinoma (CCA) of the vagina and cervix, and reproductive anomalies. Used in the treatment of prostate cancer to block the production of testosterone.

Signalwort

Danger

Gefahreneinstufungen

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

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

WGK

WGK 3

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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45315

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Sigma-Aldrich

F9397

Flutamid

β-Estradiol ≥98%

Sigma-Aldrich

E8875

β-Estradiol

Estriol ≥97%

Sigma-Aldrich

E1253

Estriol

Screening of potentially hormonally active chemicals using bioluminescent yeast bioreporters
Sanseverino J, et al.
Toxicological Sciences, 107(1), 122-134 (2008)
Effects of diethylstilbestrol on the proliferation and tyrosinase activity of cultured human melanocytes
Tang J, et al.
Biomedical Reports, 3(4), 499-502 (2015)
Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes.
Jorgensen M, et al.
Environmental Health Perspectives, 108(5), 403-403 (2000)
Hanna K L Johansson et al.
Reproductive toxicology (Elmsford, N.Y.), 101, 9-17 (2021-02-12)
Developmental exposure to endocrine disrupting chemicals can have negative consequences for reproductive health in both men and women. Our knowledge about how chemicals can cause adverse health outcomes in females is, however, poorer than our knowledge in males. This is
Aimee A D'Aloisio et al.
Epidemiology (Cambridge, Mass.), 24(2), 277-284 (2013-01-26)
Early menarche is related to increased risk of breast cancer. The number of established factors that contribute to early menarche is limited. We studied prenatal and infant exposures in relation to age at menarche in a nationwide cohort of women
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