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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%

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCK1818
MKCD2519
MKBW5248V
MKBR4347V
MKBP5170V

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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
Diethylstilbestrol cis-trans isomerization and estrogen activity of diethylstilbestrol isomers.
V W Winkler et al.
Steroids, 17(2), 197-207 (1971-02-01)
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
S T Jan et al.
Chemical research in toxicology, 11(5), 408-411 (1998-06-20)
Diethylstilbestrol (DES) and hexestrol (HES) are carcinogenic synthetic estrogens. The major metabolites of these compounds are their catechol derivatives, 3'-OH-DES and 3'-OH-HES. Oxidation of these metabolites leads to the electrophilic quinones, which are presumably involved in the tumor-initiating process. A
Robert W Yeh et al.
Journal of the American College of Cardiology, 65(20), 2211-2221 (2015-03-20)
The benefits and risks of prolonged dual antiplatelet therapy may be different for patients with acute myocardial infarction (MI) compared with more stable presentations. This study sought to assess the benefits and risks of 30 versus 12 months of dual
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