Hexestrol

Structural formula
	Structural formula without representation of the stereoisomerism
General
Surname	Hexestrol
other names	4,4 '- (1,2-diethylethylene) diphenol; 3,4-bis (4-hydroxyphenyl) hexane; Dihydrodiethylstilbestrol;
Molecular formula	C 18 H 22 O 2
Brief description	white odorless solid
External identifiers / databases
EC number	201-518-1
ECHA InfoCard	100.001.380
PubChem	192197
ChemSpider	166848
DrugBank	DB07931
Wikidata	Q27461267
properties
Molar mass	270.37 g mol −1
Physical state	firmly
Melting point	185–188 ° C ( meso ); 128 ° C ( D / L );
solubility	freely soluble in ether ; soluble in acetone , ethanol , methanol and vegetable oils; slightly soluble in chloroform and benzene ; practically insoluble in water;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 350
	P: 201-308 + 313
Toxicological data	2000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexestrol ( INN ) (formerly German Hexöstrol ; also known as Hexanestrol , Hexoestrol and Dihydrodiethylstilbestrol ), is a synthetic , non- steroidal estrogen of the stilbestrol group related to diethylstilbestrol that was used to treat hypoestrogenism but is no longer used medicinally today.

Stereoisomerism

Hexestrol has two similarly substituted stereocenters, consequently there are three stereoisomers, the ( R , R ) form, the ( S , S ) form (also known as sinestrol ) and the meso form. Isohexestrol or DL -hexestrol unspecifically denotes the ( R , R ) form, ( S , S ) form or a mixture of both.

Isomers of Hexestrol
Surname	( R , R ) -hexestrol	( S , S ) -hexestrol	meso- hexestrol
other names		Sinestrol
	Isohexestrol DL -hexestrol
Structural formula
CAS number	53625-22-2	29555-62-2	84-16-2
	5776-72-7 [( R , R ) or ( S , S )]
	5635-50-7 (unspec.)
EC number	-	-	201-518-1
	227-082-2 (unspec.)
ECHA info card	-	-	100.001.380
	100.024.621 (unspec.)
PubChem	273497115	688058	192197
	234907 [( R , R ) or ( S , S )]
	3606 (unspec.)
Wikidata		Q61807120	Q27461267
	Q27285317 [( R , R ) or ( S , S )]
	Q5896882 (unspec.)

Extraction and presentation

Hexestrol is a synthetic hydrogenated derivative of diethylstilbestrol. The hydrogenation of the dimethyl ethers of diethylstilbestrol or pseudodiethylstilbestrol and subsequent demethylation produces the meso isomer, which has a stronger effect than the mixture of isomers. It is also possible to prepare by hydrogenating 4,4'-dihydroxydiphenylhexadiene, by reacting ethylmagnesium bromide with anisaldazine and subsequent demethylation, or starting from p- hydroxypropiophenone.

Hexestrol dimethyl ether can be obtained from anethole hydrobromide by reacting with a Grignard reagent in the presence of a cobalt , nickel or iron halide.

properties

Hexestrol is a white, odorless and tasteless solid that is practically insoluble in water. It is relatively stable at room temperature.

safety instructions

Hexestrol is known to be carcinogenic.

brand names

Synestrol , Synoestrol , Estrifar , Estronal , Hormoestrol , numerous others. The preparations are no longer on the market.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Klaus Florey: Profiles of Drug Substances, Excipients and Related Methodology . Academic Press, 1982, ISBN 978-0-08-086106-7 , pp. 360 ( limited preview in Google Book Search).
↑ ^a ^b ^c ^d data sheet Hexestrol, analytical standard at Sigma-Aldrich , accessed on February 8, 2016 ( PDF ).
↑ Entry on Hexestrol. In: Römpp Online . Georg Thieme Verlag, accessed on February 8, 2016.
↑ IK Morton, Judith M. Hall: Concise Dictionary of Pharmacological Agents: Properties and Definitions . Springer Science & Business Media, December 6, 2012, ISBN 978-94-011-4439-1 , p. 140.
^ J. Elks: The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer, November 14, 2014, ISBN 978-1-4757-2085-3 , pp. 162-163.
↑ John A. Thomas: Endocrine Toxicology, Second Edition . CRC Press, March 12, 1997, ISBN 978-1-4398-1048-4 , p. 144.
↑ Franz v. Bruchhausen, G. Dannhardt, Siegfried Ebel, August Wilhelm Frahm, Eberhard Hackenthal, Ulrike Holzgrabe: Hager's Handbook of Pharmaceutical Practice Volume 8: Substances EO . Springer-Verlag, 2013, ISBN 978-3-642-57994-3 , pp. 432 ( limited preview in Google Book search).
↑ Joachim G. Liehr, Annie M. Ballatore, Beverly B. Dague, Aysegul Ari Ulubelen: Carcinogenicity and metabolic activation of hexestrol. In: Chemico-Biological Interactions . 55, 1985, p. 157, doi: 10.1016 / S0009-2797 (85) 80125-3 .

[Klaus_Florey-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Klaus Florey: Profiles of Drug Substances, Excipients and Related Methodology . Academic Press, 1982, ISBN 978-0-08-086106-7 , pp. 360 ( limited preview in Google Book Search).

[Sigma-2] ta sheet Hexestrol, analytical standard at Sigma-Aldrich , accessed on February 8, 2016 ( PDF ).

[roempp-3] Entry on Hexestrol. In: Römpp Online . Georg Thieme Verlag, accessed on February 8, 2016.

[MortonHall2012-4] IK Morton, Judith M. Hall: Concise Dictionary of Pharmacological Agents: Properties and Definitions . Springer Science & Business Media, December 6, 2012, ISBN 978-94-011-4439-1 , p. 140.

[Elks2014-5] J. Elks: The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer, November 14, 2014, ISBN 978-1-4757-2085-3 , pp. 162-163.

[Thomas1997-6] John A. Thomas: Endocrine Toxicology, Second Edition . CRC Press, March 12, 1997, ISBN 978-1-4398-1048-4 , p. 144.

[Franz_v._Bruchhausen,_G._Dannhardt,_Siegfried_Ebel,_August_Wilhelm_Frahm,_Eberhard_Hackenthal,_Ulrike_Holzgrabe-7] Franz v. Bruchhausen, G. Dannhardt, Siegfried Ebel, August Wilhelm Frahm, Eberhard Hackenthal, Ulrike Holzgrabe: Hager's Handbook of Pharmaceutical Practice Volume 8: Substances EO . Springer-Verlag, 2013, ISBN 978-3-642-57994-3 , pp. 432 ( limited preview in Google Book search).

[DOI10.1016/S0009-2797(85)80125-3-8] Joachim G. Liehr, Annie M. Ballatore, Beverly B. Dague, Aysegul Ari Ulubelen: Carcinogenicity and metabolic activation of hexestrol. In: Chemico-Biological Interactions . 55, 1985, p. 157, doi: 10.1016 / S0009-2797 (85) 80125-3 .