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D4628

Diethylstilbestrol

Name: Diethylstilbestrol
Brand: SIGMA

≥99% (HPLC), Synthetic estrogen, powder

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

NACRES:

NA.77

PubChem Substance ID:

24893887

UNSPSC Code:

51111800

EC Number:

200-278-5

MDL number:

MFCD00002373

Beilstein/REAXYS Number:

2056095

Assay:

≥99% (HPLC)

Form:

powder

Quality level:

200

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Product Name

Diethylstilbestrol, ≥99% (HPLC)

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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Related Categories

Bioactive Small Molecules

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.

pictograms

GHS08,GHS07,GHS09

signalword

Danger

hcodes

H315,H319,H335,H350,H360FD,H410

pcodes

P202 - P261 - P273 - P302 + P352 - P305 + P351 + P338 - P308 + P313

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

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

wgk

WGK 3

ppe

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

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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)

Prenatal and infant exposures and age at menarche.

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

Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.

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

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Articles

Carcinogenesis and Epigenetics

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

Global Trade Item Number

SKU	GTIN
D4628-10G	04061833565513
D4628-5G	04061833565544
D4628-1G	04061833565520
D4628-25G	04061833565537

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