anol

{{Short description|Pair of stereoisomers}}

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{{Distinguish|Cyclohexanol}}

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| IUPAC_name = 4-(Prop-1-en-1-yl)phenol

| image = Anol.svg

| width = 250

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| CAS_number_Ref =

| CAS_number = 85960-81-2

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = VQ6PDW0YG3

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| ATC_prefix = None

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| PubChem = 415627

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| ChemSpiderID = 367976

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| C=9 | H=10 | O=1

| smiles = CC=CC1=CC=C(C=C1)O

| StdInChI_Ref =

| StdInChI = 1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2-7,10H,1H3

| StdInChIKey_Ref =

| StdInChIKey = UMFCIIBZHQXRCJ-UHFFFAOYSA-N

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}}

Anol, also known as p-hydroxypropenylbenzene,{{cite journal| vauthors = Dodds EC |title=Synthetic œstrogens in treatment|journal=The Irish Journal of Medical Science|volume=25|issue=7|year=2008|pages=307|issn=0021-1265|doi=10.1007/BF02950685|s2cid=58062466}} is a simple phenol that was derived via demethylation from anethole, an estrogenic constituent of anise and fennel, by Sir Charles Dodds in 1937.{{cite book| vauthors = Maximov PY, McDaniel RE, Jordan VC |title=Tamoxifen: Pioneering Medicine in Breast Cancer|url=https://books.google.com/books?id=p-W5BAAAQBAJ&pg=PA3|date=23 July 2013|publisher=Springer Science & Business Media|isbn=978-3-0348-0664-0|pages=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. 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.{{cite journal|title=The nature of the oestrogenic substances produced during the demethylation of anethole|journal=Proceedings of the Royal Society of London. Series B, Biological Sciences|volume=128|issue=851|year=1940|pages=253–262|issn=2053-9193|doi=10.1098/rspb.1940.0009|bibcode=1940RSPSB.128..253C|doi-access=| vauthors = Campbell NR, Dodds EC, Lawson W |s2cid=98223820 }}

{{cite book | vauthors = Dodds EC | chapter = Possibilities in the Realm of Synthetic Estrogens | veditors = Thimann KV|title=Vitamins and Hormones|url=https://archive.org/details/in.ernet.dli.2015.5563|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=[https://archive.org/details/in.ernet.dli.2015.5563/page/n252 232]–}}{{cite book| vauthors = Ravina E | chapter = Sex hormones and derivatives: Natural and Synthetic (Non-Steroidal) Estrogen and Androgens | title = The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs | chapter-url = https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA177 |date=11 January 2011|publisher=John Wiley & Sons|isbn=978-3-527-32669-3|pages=177–}}{{cite journal | vauthors = Solmssen UV | title = Synthetic estrogens and the relation between their structure and their activity | journal = Chemical Reviews | volume = 37 | issue = 3 | pages = 481–598 | date = December 1945 | pmid = 21013428 | doi = 10.1021/cr60118a004 }} Dodds later synthesized the structurally related and extremely potent estrogen diethylstilbestrol in 1938.