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218944

Sigma-Aldrich

Diethylstilbestrol, mixture of cis and trans

97%

Synonym(s):

DES

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About This Item

Empirical Formula (Hill Notation):
C18H20O2
CAS Number:
6898-97-1
Molecular Weight:
268.35
EC Number:
200-278-5
MDL number:
MFCD00002373
UNSPSC Code:
12352100
PubChem Substance ID:
24853100
NACRES:
NA.22

Assay

97%

mp

170-172 °C (lit.)

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)

General description

Mechanisms of the isomerization processes of molecular and anionic diethylstilbestrol (DES) has been reported. Estrogen activity of cis- and trans-diethylstilbestrol has been evaluated. Diethylstilbestrol is a carcinogenic synthetic estrogen.

Application

Diethylstilbestrol was used as internal standard for the analysis of drug residues in urine of rats and calves by on-line HPLC with ultraviolet and continuous-flow fast atom bombardmentmass spectrometry detectors.

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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Diethylstilbestrol cis-trans isomerization and estrogen activity of diethylstilbestrol isomers.
V W Winkler et al.
Steroids, 17(2), 197-207 (1971-02-01)
E Davoli et al.
Analytical chemistry, 65(19), 2679-2685 (1993-10-01)
An automatic system for the on-line extraction and analysis of diethylstilbestrol in the urine of rats and calves is described. Extraction was done by injecting samples directly into an immunoaffinity column containing antidiethylstilbestrol antibodies bound to a Sepharose matrix, and
Osamu Takenouchi et al.
Bioconjugate chemistry, 27(11), 2689-2694 (2016-10-04)
Estrogens regulate different physiological systems with wide ranges of concentrations. The rapid analysis of estrogens is crucially important for drug discovery and medical diagnosis, but quantitation of nanomolar estrogens in live cells persists as an important challenge. We herein describe
Shoichi Kuramitsu et al.
JACC. Cardiovascular interventions, 8(9), 1180-1188 (2015-07-27)
This study sought to assess the incidence and clinical impact of stent fracture (SF) after the PROMUS Element platinum-chromium everolimus-eluting stent (PtCr-EES). SF remains an unresolved, clinically relevant issue, even in the newer-generation drug-eluting stent era. From March 2012 to
Rami Haddad et al.
Toxicology and applied pharmacology, 266(1), 27-37 (2012-11-13)
Pregnant women, and thus their fetuses, are exposed to many endocrine disruptor compounds (EDCs). Fetal cardiomyocytes express sex hormone receptors making them potentially susceptible to re-programming by estrogenizing EDCs. Diethylstilbestrol (DES) is a proto-typical, non-steroidal estrogen. We hypothesized that changes
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