Anol

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Anol
Anol.svg
Clinical data
ATC code
  • None
Identifiers
  • 4-(Prop-1-en-1-yl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC9H10O
Molar mass134.178 g·mol−1
3D model (JSmol)
  • CC=CC1=CC=C(C=C1)O
InChI
  • 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 para-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[]

  • Dianethole

References[]

  1. ^ Dodds, E. C. (2008). "Synthetic œstrogens in treatment". The Irish Journal of Medical Science. 25 (7): 305–314. doi:10.1007/BF02950685. ISSN 0021-1265. S2CID 58062466.
  2. ^ a b c d Philipp Y. Maximov; Russell E. McDaniel; V. Craig Jordan (23 July 2013). Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 3–. ISBN 978-3-0348-0664-0.
  3. ^ a b Vitamins and Hormones. Academic Press. 1 January 1945. pp. 232–. ISBN 978-0-08-086600-0.
  4. ^ Campbell, N. R.; Dodds, E. C.; 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.
  5. ^ a b Enrique Ravina (11 January 2011). 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 (1945). "Synthetic estrogens and the relation between their structure and their activity". Chem. Rev. 37 (3): 481–598. doi:10.1021/cr60118a004. PMID 21013428.


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