# Juncusol

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> Source: https://en.wikipedia.org/wiki/Juncusol
> Source revision: 1197214995
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{{chembox
| ImageFile = Juncusol.svg
| ImageCaption = 
| PIN = 5-Ethenyl-1,6-dimethyl-9,10-dihydrophenanthrene-2,7-diol
| OtherNames = 1,6-Dimethyl-5-vinyl-9,10-dihydro-2,7-phenanthrenediol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 62023-90-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6T481HU7OI
| ChEBI_Ref = 
| ChEBI = 
| ChemSpiderID_Ref = 
| ChemSpiderID = 65579
| KEGG_Ref = 
| KEGG = 
| PubChem = 72740
| SMILES = CC1=C(C=CC2=C1CCC3=CC(=C(C(=C32)C=C)C)O)O
| EINECS = 
| StdInChI = 1S/C18H18O2/c1-4-13-10(2)17(20)9-12-5-6-14-11(3)16(19)8-7-15(14)18(12)13/h4,7-9,19-20H,1,5-6H2,2-3H3
| StdInChIKey = XNVMKPYDOHZJLR-UHFFFAOYSA-N
| RTECS = 
| MeSHName = 
  }}
|Section2={{Chembox Properties
| C=18
| H=18
| O=2
| Appearance = 
| Density = 
| MeltingPtC = 
| BoilingPtC = 
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 
| AutoignitionPt =
  }}
}}

'''Juncusol''' is a 9,10-dihydrophrenathrene found in ''Juncus'' species such as ''[J. acutus](/source/Juncus_acutus)'',<ref>{{cite journal | doi = 10.1248/cpb.55.1264| title = Phenanthrenoids from Juncus acutus L., New Natural Lipopolysaccharide-Inducible Nitric Oxide Synthase Inhibitors| journal = Chemical & Pharmaceutical Bulletin| volume = 55| issue = 8| pages = 1264| year = 2007| last1 = Behery| first1 = Fathi Abdelmohsen Abdelhalim| last2 = Naeem| first2 = Zain Elabdin Metwally| last3 = Maatooq| first3 = Galal Taha| last4 = Amer| first4 = Mohamed Mahmoud Abdelfattah| last5 = Wen| first5 = Zhi-Hong| last6 = Sheu| first6 = Jyh-Horng| last7 = Ahmed| first7 = Atallah Fouad| doi-access = free}}</ref> ''[J. effusus](/source/Juncus_effusus)''<ref>{{cite journal | author = Bhattacharyya | journal = Experientia | volume = 36 | date = 1980 | pages = 27–28 | doi=10.1007/bf02003949 | title=Structure of effusol: A new phenolic constituent from Juncus effusus| s2cid = 41731083 }}</ref><ref>{{cite journal | author = Shima | journal = Phytochemistry | volume = 30 | date = 1991 | pages = 3149–3151 | doi=10.1016/s0031-9422(00)98276-1 | title=Phenanthrene derivatives from the medullae of Juncus effusus| issue = 9 }}</ref> or ''[J. roemerianus](/source/Juncus_roemerianus)''.<ref name=Chapatwala1981>{{cite journal | doi = 10.1016/0024-3205(81)90609-3| pmid = 6796796| title = Antimicrobial activity of juncusol, a novel 9-10-dihydrophenanthrene from the marsh plant| journal = Life Sciences| volume = 29| issue = 19| pages = 1997–2001| year = 1981| last1 = Chapatwala| first1 = Kirit D.| last2 = de la Cruz| first2 = Armando A.| last3 = Miles| first3 = D.Howard}}</ref><ref>{{cite journal | pmid= 830696| year= 1977| last1= Miles| first1= D. H.| title= The structure of juncusol. A novel cytotoxic dihydrophenanthrene from the Estuarine marsh plant Juncus roemerianus| journal= Journal of the American Chemical Society| volume= 99| issue= 2| pages= 618–20| last2= Bhattacharyya| first2= J| last3= Mody| first3= N. V.| last4= Atwood| first4= J. L.| last5= Black| first5= S| last6= Hedin| first6= P. A.| doi=10.1021/ja00444a056}}</ref>

It can also be synthesized.<ref>{{cite journal | doi = 10.1016/S0040-4039(01)85715-4| title = Total synthesis of juncusol| journal = Tetrahedron Letters| volume = 19| issue = 47| pages = 4723| year = 1978| last1 = McDonald| first1 = Edward| last2 = Martin| first2 = Roger T.}}</ref><ref>{{cite journal | doi = 10.1021/jo00195a034| title = Regiospecific total synthesis of juncusol| journal = The Journal of Organic Chemistry| volume = 49| issue = 21| pages = 4045| year = 1984| last1 = Boger| first1 = Dale L.| last2 = Mullican| first2 = Michael D.}}</ref><ref>{{cite journal | doi = 10.1016/S0040-4039(00)79645-6| title = A novel synthesis of juncusol| journal = Tetrahedron Letters| volume = 32| issue = 10| pages = 1279| year = 1991| last1 = Jacobi| first1 = Peter A.| last2 = Zheng| first2 = Wanjun}}</ref>

This compound shows antimicrobial activity against ''[Bacillus subtilis](/source/Bacillus_subtilis)'' and ''[Staphylococcus aureus](/source/Staphylococcus_aureus)''.<ref name=Chapatwala1981/> It also has a toxic effect on estuarine fish and shrimp.<ref>{{cite journal | pmid= 7098770| year= 1982| last1= de la Cruz| first1= A. A.| title= Toxic effects of juncusol, a marsh plant phenolic extract, on estuarine fish and shrimp| journal= Life Sciences| volume= 30| issue= 21| pages= 1805–10| last2= Miles| first2= D. H.| last3= Chapatwala| first3= K. D.| doi=10.1016/0024-3205(82)90317-4}}</ref>

== References ==
{{reflist}}

== External links ==
* [http://kanaya.naist.jp/knapsack_jsp/information.jsp?word=C00015801 Juncusol at kanaya.naist.jp/knapsack_jsp]

Category:Phenanthrenoids
Category:Vinyl compounds

{{phenol-stub}}

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Adapted from the Wikipedia article [Juncusol](https://en.wikipedia.org/wiki/Juncusol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Juncusol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.