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D4628

Sigma-Aldrich

Diethylstilbestrol

≥99% (HPLC)

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Synonym(s):
(E)-3,4-Bis(4-hydroxyphenyl)-3-hexene, DES, Stilbestrol
Empirical Formula (Hill Notation):
C18H20O2
CAS Number:
56-53-1
Molecular Weight:
268.35
Beilstein:
2056095
EC Number:
200-278-5
MDL number:
MFCD00002373
PubChem Substance ID:
24893887
NACRES:
NA.77

Quality Level

200

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+

InChI key

RGLYKWWBQGJZGM-ISLYRVAYSA-N

Gene Information

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

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Application

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 Actions

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.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Screening of potentially hormonally active chemicals using bioluminescent yeast bioreporters
Sanseverino J, et al.
Toxicological Sciences, 107(1), 122-134 (2008)
Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes.
Jorgensen M, et al.
Environmental Health Perspectives, 108(5), 403-403 (2000)
Effects of diethylstilbestrol on the proliferation and tyrosinase activity of cultured human melanocytes
Tang J, et al.
Biomedical Reports, 3(4), 499-502 (2015)
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
Pierre-Olivier Bosset et al.
BJU international, 110(11 Pt C), E826-E829 (2012-05-15)
What's known on the subject? and What does the study add? Diethylstilbestrol (DES) has been found to have anti-tumour properties and clinical effectiveness in prostate cancer that is resistant to the first-line hormonal therapy. This review found that low-dose DES
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