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Anol

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Anol
Clinical data

ATC code	None
Identifiers
IUPAC name 4-(Prop-1-en-1-yl)phenol
CAS Number	85960-81-2
PubChem CID	415627
ChemSpider	367976
UNII	VQ6PDW0YG3
CompTox Dashboard (EPA)	DTXSID401345962
Chemical and physical data
Formula	C₉H₁₀O
Molar mass	134.178 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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]

References[edit]

^ 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.

^ ^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.

^ ^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.

^ 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.

^ ^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.

^ 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.