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H7753

Supelco

Hexestrol

analytical standard

Synonym(s):

4,4′-(1,2-Diethylethylene)diphenol, meso-3,4-Bis(4-hydroxyphenyl)hexane, Dihydrodiethylstilbestrol

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About This Item

Empirical Formula (Hill Notation):
C18H22O2
CAS Number:
84-16-2
Molecular Weight:
270.37
Beilstein/REAXYS Number:
3209460
EC Number:
201-518-1
MDL number:
MFCD00068996
UNSPSC Code:
41116107
PubChem Substance ID:
329815246
NACRES:
NA.24

grade

analytical standard

Quality Level

100

assay

≥98%

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

SMILES string

CC[C@H]([C@H](CC)c1ccc(O)cc1)c2ccc(O)cc2

InChI

1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+

InChI key

PBBGSZCBWVPOOL-HDICACEKSA-N

Gene Information

human ... ESR1(2099)
rat ... Esr1(24890)

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General description

Hexestrol is a synthetic nonsteroidal estrogen,[1] which can be used in human medicine as well as a growth promoter in cattle.[2]

Application

Hexestrol may be used as a reference standard for the determination of the analyte in biological samples using immunoaffinity extraction and gas chromatography-negative-ion chemical ionization mass spectrometry.[2]
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

The carcinogen hexestrol is a nonsteroidal synthetic estrogen. Metabolic activation of hexestrol to its quinone, which reacts with DNA to form analogous depurinating adducts, may be a primary critical event leading to oncogenic mutations and cancer initiation.

Linkage

Reduced analogue of diethylstilbestrol.

Recommended products

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H350

Hazard Classifications

Carc. 1B

Storage Class

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

wgk_germany

WGK 2

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM4126
MKCK7639
MKCK4408
MKCH4229
MKCC7215

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Analysis of diethylstilbestrol, dienestrol and hexestrol in biological samples by immunoaffinity extraction and gas chromatography-negative-ion chemical ionization mass spectrometry.
Bagnati R, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 527, 267-278 (1990)
A R Pop et al.
Romanian journal of morphology and embryology = Revue roumaine de morphologie et embryologie, 52(1 Suppl), 413-417 (2011-04-01)
The research was performed on 24 male sexually mature domestic rabbits, divided in two equal batches. The rabbits from the first batch were administered 0.5 mg/kg of body weight hexestrol diacetate intramuscularly twice a week for four consecutive weeks. Batch
Catherine Hulot et al.
Journal of the American Chemical Society, 130(15), 5046-5047 (2008-03-20)
Fenestranes are regarded as a particularly challenging synthetic targets, and only few syntheses have been reported in the recent past. These rare compounds of synthetic and theoretical interest are a class of tetracyclic skeletons, defined as doubly a,a'-bridged spiroalkanes. The
M M Vdovenko et al.
Prikladnaia biokhimiia i mikrobiologiia, 47(1), 84-89 (2011-03-30)
An indirect competitive enzyme-linked immunosorbent assay (ELISA) of hexestrol (HES), an antibiotic forbidden for use in livestock farming, has been developed. Conditions of ELISA have been optimized by varying the concentrations of the coating conjugate (HES-ovalbumin), anti-HES antiserum, casein, and
Muhammad Saeed et al.
Steroids, 70(1), 37-45 (2004-12-22)
The nonsteroidal synthetic estrogen hexestrol (HES), which is diethylstilbestrol hydrogenated at the C-3-C-4 double bond, is carcinogenic. Its major metabolite is the catechol, 3'-OH-HES, which can be metabolically converted to the catechol quinone, HES-3',4'-Q. Study of HES was undertaken with
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