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Hexestrol

analytical standard

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

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Properties

Related Categories Additional Drugs, Additional Standards, Analytical Standards, Analytical/Chromatography, Chromatography,
grade   analytical standard
assay   ≥98%
form   neat
format   neat
Gene Information   human ... ESR1(2099)
rat ... Esr1(24890)

Description

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.

Packaging

1, 5 g in poly bottle

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
45
Safety Statements (Europe) 
53-45
WGK Germany 
2
RTECS 
SL0560850

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

DNA Damage and Repair

Damage to cellular DNA is involved in mutagenesis and the development of cancer. The DNA in a human cell undergoes several thousand to a million damaging events per day, generated by both external (e...
BioFiles 2007, 2.4, 20.
Keywords: AGE, Alkylations, Apoptosis, Applications, Biochemistry, Cancer, Carcinogens, Catalysis, Clinical, DNA replication, Deaminations, Environmental, Error, Events, Gene expression, Metabolites, Methylations, Mutagens, Oxidations, Polymorphisms, Rearrangements, Recombination, Sequences, Substitutions, Transcription, Type

Peer-Reviewed Papers

References

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Structure of the G225P/G226P mutant of mouse 3(17)alpha-hydroxysteroid dehydrogenase (AKR1C21) ternary complex: implications for the binding of inhibitor and substrate. Dhagat U, Endo S, Mamiya H, et al. Acta Crystallogr. D Biol. Crystallogr. 65(Pt 3), 257-65, (2009)

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[Enzyme immunoassay for the determination of hexestrol in meat]. Vdovenko MM, Peng CF, Xu CL, et al. Prikl. Biokhim. Mikrobiol. 47(1), 84-9, (2011)

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[Effects of Yi Fu Ning soft gelatin capsules on reproductive endocrine-immune function of ovariectomized rats]. Wu ZX, Wang XH, and Deng HZ Zhong Yao Cai 32(7), 1083-6, (2009)

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[Determination of hormone multi-residues in animal tissues by gas chromatography-mass spectrometry]. Lin W, Dong W, Chen X, et al. Se Pu 27(3), 294-8, (2009)

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[Hexestrol inhibits ATP-induced contractile response of isolated preparations of pregnant human uterus]. Ziganshin AU, Ablaeva DN, Khasanov AA, et al. Eksp. Klin. Farmakol. 71(6), 20-2, (2008)

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Synthesis of [4.6.4.6]fenestradienes and [4.6.4.6]fenestrenes based on an 8pi-6pi-cyclization-oxidation cascade. Hulot C, Blond G, and Suffert J J. Am. Chem. Soc. 130(15), 5046-7, (2008)

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[Determination of residues of three stilbene drugs in animal tissues using gas chromatography-mass spectrometry]. Wu Y, Liu S, Hou D, et al. Se Pu 24(5), 462-5, (2006)

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Drug-induced steatohepatitis. Stravitz RT and Sanyal AJ Clin. Liver Dis. 7(2), 435-51, (2003)

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Dynamic liquid-liquid-solid microextraction based on molecularly imprinted polymer filaments on-line coupling to high performance liquid chromatography for direct analysis of estrogens in complex samples. Zhong Q, Hu Y, Hu Y, et al. J. Chromatogr. A 1241, 13-20, (2012)

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Metabolic activation and formation of DNA adducts of hexestrol, a synthetic nonsteroidal carcinogenic estrogen. Jan ST, Devanesan PD, Stack DE, et al. Chem. Res. Toxicol. 11(5), 412-9, (1998)

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Steatohepatitis-inducing drugs trigger cytokeratin cross-links in hepatocytes. Possible contribution to Mallory-Denk body formation. Robin MA, Descatoire V, Pessayre D, et al. Toxicol. In Vitro 22(6), 1511-9, (2008)

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On-line coupling of pressurized capillary electrochromatography with end-column amperometric detection for analysis of estrogens. Liu S, Wu X, Xie Z, et al. Electrophoresis 26(12), 2342-50, (2005)

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Trace analysis of diethylstilbestrol, dienestrol and hexestrol in environmental water by Nylon 6 nanofibers mat-based solid-phase extraction coupled with liquid chromatography-mass spectrometry. Xu Q, Wang M, Yu S, et al. Analyst 136(23), 5030-7, (2011)

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Validation of screening method for residues of diethylstilbestrol, dienestrol, hexestrol, and zeranol in bovine urine using immunoaffinity chromatography and gas chromatography/mass spectrometry. Dickson LC, MacNeil JD, Reid J, et al. J. AOAC Int. 86(4), 631-9, (2003)

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Effects of hexestrol on mouse ovarian morphology and ovulation. de Oliveira JM, Simões MJ, Mora OA, et al. Maturitas 60(2), 153-7, (2008)

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Positive and negative discrimination of estrogen receptor agonists and antagonists using site-specific DNA recombinase fusion proteins. Logie C, Nichols M, Myles K, et al. Mol. Endocrinol. 12(8), 1120-32, (1998)

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Studies on thermal reactivity of beta-(1,2-allenyl)butenolides and 2-allyl-3-allenylcyclohex-2-enones. Gu Z and Ma S Chemistry 14(8), 2453-64, (2008)

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Large-scale synthesis of the catechol metabolites of diethylstilbestrol and hexestrol. Jan ST, Rogan EG, and Cavalieri EL Chem. Res. Toxicol. 11(5), 408-11, (1998)

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Determination of hexoestrol residues in animal tissues based on enzyme-linked immunosorbent assay and comparison with liquid chromatography-tandem mass spectrometry. Xu C, Peng C, Liu L, et al. J. Pharm. Biomed. Anal. 41(3), 1029-36, (2006)

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Formation of the depurinating N3adenine and N7guanine adducts by reaction of DNA with hexestrol-3',4'-quinone or enzyme-activated 3'-hydroxyhexestrol. Implications for a unifying mechanism of tumor initiation by natural and synthetic estrogens. Saeed M, Gunselman SJ, Higginbotham S, et al. Steroids 70(1), 37-45, (2005)

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Comparison of the diagnostic accuracy of di-22:6-bis(monoacylglycerol)phosphate and other urinary phospholipids for drug-induced phospholipidosis or tissue injury in the rat. Thompson KL, Haskins K, Rosenzweig BA, et al. Int. J. Toxicol. 31(1), 14-24, (2012)

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[Effects of veterinary drugs on beta-hexosaminidase release from rat basophilic leukemia cells (RBL-2H3)]. Tanaka Y, Taguchi S, Yoshida S, et al. Shokuhin Eiseigaku Zasshi 43(5), 306-11, (2002)

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[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals]. Tanaka Y, Taguchi S, Yoshida S, et al. Shokuhin Eiseigaku Zasshi 45(2), 100-5, (2004)

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Comparison of time-resolved fluoroimmunoassay for determining hexoestrol residues in chicken muscle tissues based on polyclonal antibodies with liquid chromatography and tandem mass spectrometry. Xiangqian L, Yongming H, Tieming H, et al. Ann. Chim. 97(3-4), 177-86, (2007)

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The influence of hexestrol diacetate on gametogene function in male rabbit. Pop AR, Groza I, Miclăuş V, et al. Rom. J. Morphol. Embryol. 52(1 Suppl), 413-7, (2011)

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Merck 14,4701

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