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D4628

Sigma-Aldrich

Diethylstilbestrol

≥99% (HPLC)

Synonym(s):

(E)-3,4-Bis(4-hydroxyphenyl)-3-hexene, DES, Stilbestrol

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About This Item

Empirical Formula (Hill Notation):
C18H20O2
CAS Number:
56-53-1
Molecular Weight:
268.35
Beilstein:
2056095
EC Number:
200-278-5
MDL number:
MFCD00002373
UNSPSC Code:
51111800
PubChem Substance 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+

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
G G Kuiper et al.
Endocrinology, 138(3), 863-870 (1997-03-01)
The rat estrogen receptor (ER) exists as two subtypes, ER alpha and ER beta, which differ in the C-terminal ligand binding domain and in the N-terminal transactivation domain. In this study we investigated the messenger RNA expression of both ER
Leena Hilakivi-Clarke et al.
Journal of mammary gland biology and neoplasia, 18(1), 25-42 (2013-02-09)
Women are using estrogens for many purposes, such as to prevent pregnancy or miscarriage, or to treat menopausal symptoms. Estrogens also have been used to treat breast cancer which seems puzzling, since there is convincing evidence to support a link
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