View source for Anol

{{Short description|Pair of stereoisomers}}
{{cs1 config|name-list-style=vanc}}
{{Distinguish|Cyclohexanol}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = 4-(Prop-1-en-1-yl)phenol
| image = Anol.svg
| width = 250

<!--Clinical data-->
| tradename = 
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = 
| legal_UK = 
| legal_US = 
| legal_status = 
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =

<!-- Identifiers -->
| CAS_number_Ref = 
| CAS_number = 85960-81-2
| CAS_supplemental = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VQ6PDW0YG3
| ATCvet = 
| ATC_prefix = None
| ATC_suffix = 
| ATC_supplemental = 
| PubChem = 415627
| IUPHAR_ligand = 
| DrugBank_Ref = 
| DrugBank = 
| ChemSpiderID_Ref = 
| ChemSpiderID = 367976
| KEGG = 
| ChEBI = 
| ChEMBL =

<!--Chemical data-->
| 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
| synonyms = 
}}

'''Anol''', also known as '''''p''-hydroxypropenylbenzene''',<ref name="Dodds2008">{{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}}</ref> is a simple [[phenol]] that was derived via [[demethylation]] from [[anethole]], an [[estrogen]]ic constituent of [[anise]] and [[fennel]], by [[Sir Charles Dodds]] in 1937.<ref name="MaximovMcDaniel2013">{{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–}}</ref><ref name="AcademicPress1945" /> It was reported to possess extremely potent estrogenic activity on par with that of [[steroid]]al estrogens like [[estrone]], with a dose of 1&nbsp;μg inducing [[estrus]] in rats.<ref name="MaximovMcDaniel2013" /> However, subsequent studies with different preparations of anol failed to confirm these findings, and it was found that [[dimer (chemistry)|dimerization]] of anol into [[dianol]] and [[hexestrol]] can rapidly occur and that the latter impurity was responsible for the highly potent estrogenic effects.<ref>{{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 }}</ref>
<ref name="MaximovMcDaniel2013" /><ref name="AcademicPress1945">{{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]–}}</ref><ref name="Ravina2011">{{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–}}</ref><ref name="pmid21013428">{{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 }}</ref> Dodds later synthesized the structurally related and extremely potent estrogen [[diethylstilbestrol]] in 1938.<ref name="MaximovMcDaniel2013" /><ref name="Ravina2011" />

== See also ==
* [[Dianethole]]

== References ==
{{reflist|30em}}
{{genito-urinary-drug-stub}}
{{Estrogen receptor modulators}}

[[Category:Estrogens]]
[[Category:4-Hydroxyphenyl compounds]]