Dienestrol

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Dienestrol
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
Pharmacokinetic data
Protein binding50 to 80%
Identifiers
  • 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.381 Edit this at Wikidata
Chemical and physical data
FormulaC18H18O2
Molar mass266.334 g/mol g·mol−1
3D model (JSmol)
  • Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2
  • 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+ checkY
  • Key:NFDFQCUYFHCNBW-SCGPFSFSSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dienestrol is a synthetic estrogen.

Synthesis

Dienestrol synthesis
  1. Pinacol coupling of the substituted propiophenone.
  2. Dehydration of the thus-obtained glycol with a mixture of acetyl chloride and acetic anhydride leads to the transoid diene system.
  3. Saponification removes the acetate groups and thus affords dienestrol.

Hexestrol

Hexestrol synthesis:[1][2][3] U.S. patent 2,357,985 GB 523320 

See also

References

  1. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1098/rspb.1940.0009, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1098/rspb.1940.0009 instead.
  2. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/ja01867a067, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/ja01867a067 instead.
  3. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jo01158a010, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jo01158a010 instead.
  • Dodds, E. C.; Goldberg, L.; Lawson, W.; Robinson, R.; Proc. Roy. Soc. (London) 1939, B127, 148.

External links


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