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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:
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, which can be used in human medicine as well as a growth promoter in cattle.

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.
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

Signal Word

Danger

Hazard Statements

H350

Hazard Classifications

Carc. 1B

Storage Class Code

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

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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 U Ziganshin et al.
Eksperimental'naia i klinicheskaia farmakologiia, 71(6), 20-22 (2009-01-15)
The results of in vitro experiments showed that hexestrol, a synthetic analog of estrogen hormones, at high concentrations inhibited the contractile response of isolated preparations of pregnant human uterus induced by ATP. It is suggested that estrogen hormones can interact
Li Xiangqian et al.
Annali di chimica, 97(3-4), 177-186 (2007-09-08)
A time-resolved fluoroimmunoassay (TR-FIA) was developed for the determination of hexoestrol (HES) residues in animal tissues. The limit of detection (LOD) was determined to be 0.02 ng g(-1) and the limit of quantification (LOQ) was less than 0.12 ng g(-1).
S T Jan et al.
Chemical research in toxicology, 11(5), 412-419 (1998-06-20)
Hexestrol (HES), a synthetic nonsteroidal estrogen, is carcinogenic in Syrian golden hamsters. The major metabolite of HES is its catechol, 3'-OH-HES, which can be metabolically converted to the electrophilic catechol quinone, HES-3',4'-Q, by peroxidases and cytochrome P450. Standard adducts were
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
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DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

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