Anol

Not to be confused with Cyclohexanol.
Anol
Clinical data
ATC code
  • None
Identifiers
  • 4-(Prop-1-en-1-yl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H10O
Molar mass134.178 g·mol−1
3D model (JSmol)
  • CC=CC1=CC=C(C=C1)O
  • InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2-7,10H,1H3
  • Key:UMFCIIBZHQXRCJ-UHFFFAOYSA-N

Anol, also known as p-hydroxypropenylbenzene,[1] is a simple phenol that was derived via demethylation from anethole, an estrogenic constituent of anise and fennel, by Sir Charles Dodds in 1937.[2][3] It was reported to possess extremely potent estrogenic activity on par with that of steroidal estrogens like estrone, with a dose of 1 μg inducing estrus in rats.[2] However, subsequent studies with different preparations of anol failed to confirm these findings, and it was found that dimerization of anol into dianol and hexestrol can rapidly occur and that the latter impurity was responsible for the highly potent estrogenic effects.[4] [2][3][5][6] Dodds later synthesized the structurally related and extremely potent estrogen diethylstilbestrol in 1938.[2][5]

See also

References

  1. ^ Dodds EC (2008). "Synthetic œstrogens in treatment". The Irish Journal of Medical Science. 25 (7): 307. doi:10.1007/BF02950685. ISSN 0021-1265. S2CID 58062466.
  2. ^ a b c d Maximov PY, McDaniel RE, Jordan VC (23 July 2013). Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 3–. ISBN 978-3-0348-0664-0.
  3. ^ a b Dodds EC (1 January 1945). "Possibilities in the Realm of Synthetic Estrogens". In Thimann KV (ed.). Vitamins and Hormones. Academic Press. pp. 232–. ISBN 978-0-08-086600-0.
  4. ^ Campbell NR, Dodds EC, Lawson W (1940). "The nature of the oestrogenic substances produced during the demethylation of anethole". Proceedings of the Royal Society of London. Series B, Biological Sciences. 128 (851): 253–262. Bibcode:1940RSPSB.128..253C. doi:10.1098/rspb.1940.0009. ISSN 2053-9193. S2CID 98223820.
  5. ^ a b Ravina E (11 January 2011). "Sex hormones and derivatives: Natural and Synthetic (Non-Steroidal) Estrogen and Androgens". The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. pp. 177–. ISBN 978-3-527-32669-3.
  6. ^ Solmssen UV (December 1945). "Synthetic estrogens and the relation between their structure and their activity". Chemical Reviews. 37 (3): 481–598. doi:10.1021/cr60118a004. PMID 21013428.
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