Dienestrol

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 N
PubChem CID	667476
DrugBank	DB00890 Y
ChemSpider	580857 Y
UNII	RRW32X4U1F
KEGG	D00898 Y
ChEBI	CHEBI:4518 N
ChEMBL	ChEMBL1018 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
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+ Y Key:NFDFQCUYFHCNBW-SCGPFSFSSA-N Y
NY (what is this?)  (verify)

Dienestrol is a synthetic estrogen.

Synthesis

Dienestrol synthesis:

1. Pinacol coupling of p-acetoxy-propiophenone.
2. 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).
3. Saponification removes the acetate groups and thus affords dienestrol.

See also

• Diethylstilbestrol

References

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