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bsd>JWBE: removed Category:Phenols; added Category:Hydroxyarenes using HotCat

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removed Category:Phenols; added Category:Hydroxyarenes using HotCat

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{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461094560
| IUPAC_name = (13''S'',14''S'')-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11''H''-cyclopenta[''a'']phenanthren-17-one
| image = Equilenin.svg
| width = 225px


| tradename =
| pregnancy_category =
| legal_status =
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Estrogen (medication)|Estrogen]]


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 517-09-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W8FTJ17C4J
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
| PubChem = 444865
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03515
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 392668
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14303
| ChEBI = 34739
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 225546
| synonyms = 6,8-Didehydroestrone; Estra-1,3,5(10),6,8-pentaen-3-ol-17-one


| C=18 | H=18 | O=2
| SMILES = O=C4[C@]3(CCc1c(ccc2c1ccc(O)c2)[C@@H]3CC4)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PDRGHUMCVRDZLQ-WMZOPIPTSA-N
}}

'''Equilenin''', also known as '''6,8-didehydroestrone''', as well as '''estra-1,3,5(10),6,8-pentaen-3-ol-17-one''', is a [[natural product|naturally occurring]] [[steroid]]al [[estrogen (medication)|estrogen]] obtained from the [[urine]] of [[pregnancy|pregnant]] [[mares]].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA298|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=494–}}</ref><ref name="FritzSperoff2012">{{cite book| vauthors = Fritz MA, Speroff L |title=Clinical Gynecologic Endocrinology and Infertility|url=https://books.google.com/books?id=KZLubBxJEwEC&pg=PA751|date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4847-3|pages=751–}}</ref> It is used as one of the components in [[conjugated estrogens]] (brand name Premarin).<ref name="FritzSperoff2012" /> It was the first complex natural product to be fully synthesized, in work reported by 1940 by [[Werner Emmanuel Bachmann|Bachmann]] and [[Alfred L. Wilds|Wilds]].<ref name = TS>{{cite journal|title = The Total Synthesis of the Sex Hormone Equilenin and Its Stereoisomers | vauthors = Bachmann WE, Cole W, Wilds AL |author-link1 = Werner Emmanuel Bachmann |author-link3 = Alfred L. Wilds |journal = [[J. Am. Chem. Soc.]] |year = 1940|volume = 62|issue = 4|pages = 824–839|doi = 10.1021/ja01861a036}}</ref>

==Chemistry==

===Synthesis===

====Total synthesis====
The synthesis developed by the [[Werner Emmanuel Bachmann|Bachmann]] group started from Butenand's ketone<ref name = Nicolaou /> – the 7-methoxy [[structural analog]] of [[1,2,3,4-tetrahydrophenanthren-1-one]]<ref name = TS-comm>{{cite journal|title = The Total Synthesis of the Sex Hormone Equilenin | vauthors = Bachmann WE, Cole W, Wilds AL |author-link1 = Werner Emmanuel Bachmann|author-link3 = Alfred L. Wilds|journal = [[J. Am. Chem. Soc.]]|year = 1939|volume = 61|issue = 4|pages = 974–975|doi = 10.1021/ja01873a513}}</ref> – and which can be readily prepared from 1,6-[[Cleve's acid]].<ref name = 1974review>{{cite book | vauthors = Nakanishi K |chapter = Steroids | veditors = Nakanishi K, Goto T, Itô S, Natori S, Nozoe S |title = Natural Products Chemistry|volume = 1 |publisher = [[Academic Press]]|year = 1974|pages = 421–545 |isbn = 9781483218861|chapter-url = https://books.google.com/books?id=PKb-BAAAQBAJ&pg=PA491}}</ref> The approach was based on well-established transformations like the [[Claisen condensation]], the [[Reformatsky reaction]], the [[Arndt–Eistert reaction]], and the [[Dieckmann condensation]].<ref name = TS /> [[K. C. Nicolaou|Nicolaou]] described this preparation as ending the era preceding the post-World War II work of [[Robert Burns Woodward]] that introduced [[enantioselective synthesis]];<ref name = Nicolaou>{{cite journal | vauthors = Nicolaou KC, Vourloumis D, Winssinger N, Baran PS | title = The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century | journal = Angewandte Chemie | volume = 39 | issue = 1 | pages = 44–122 | date = January 2000 | pmid = 10649349 | doi = 10.1002/(SICI)1521-3773(20000103)39:1<44::AID-ANIE44>3.0.CO;2-L | url = http://yxzx.zjnu.edu.cn/lunwen/8.pdf | access-date = 2017-07-22 | url-status = dead | archive-url = https://web.archive.org/web/20170517074054/http://yxzx.zjnu.edu.cn/lunwen/8.pdf | archive-date = 2017-05-17 | authorlink1 = K. C. Nicolaou }}</ref> in this synthesis, a mixture of stereoisomers were prepared and then [[chiral resolution|resolved]],<ref name = 1974review /> and the choice of target was partly because of the existence of only two chiral carbons and hence only four stereoisomers.<ref name = TS-comm />

[[File:Bachmann's total synthesis of equilenin.jpg|left|thumb|700px]] {{Clear}}

The overall yield of the synthesis was 2.7% based on a twenty-step process starting from Cleve's acid.<ref name = 1974review />

== See also ==
* [[List of estrogens#Equine estrogens|List of estrogens § Equine estrogens]]

== References ==
{{Reflist}}

{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}

[[Category:Sterols]]
[[Category:Hydroxyarenes]]
[[Category:Estranes]]
[[Category:Estrogens]]
[[Category:Ketones]]

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bsd>JWBE: removed Category:Phenols; added Category:Hydroxyarenes using HotCat

WikiSysop: 1版をインポートしました