Dienestrol

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Dienestrol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	G03CB01 (WHO) G03CC02 (WHO);
Pharmacokinetic data
Protein binding	50 to 80%
Identifiers
	IUPAC name 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol;
CAS Number	84-17-3 ;
PubChem CID	667476;
DrugBank	DB00890 ;
ChemSpider	580857 ;
UNII	RRW32X4U1F;
KEGG	D00898 ;
ChEBI	CHEBI:4518 ;
ChEMBL	ChEMBL1018 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C18H18O2
Molar mass	266.334 g/mol
3D model (JSmol)	Interactive image;
	SMILES Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2;
	InChI InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+ ; Key:NFDFQCUYFHCNBW-SCGPFSFSSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Dienestrol is a synthetic estrogen.

Pinacol coupling of p-acetoxy-propiophenone.
Dehydration of the thus-obtained glycol with a mixture of acetyl chloride and acetic anhydride leads to the transoid diene system (bis-β-Methylstyrene-type).
Saponification removes the acetate groups and thus affords dienestrol.