Juncusol
 Chemical structure of juncusol
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| Names | |
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| IUPAC name
5-ethenyl-1,6-dimethyl-9,10-dihydrophenanthrene-2,7-diol
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| Other names
1,6-Dimethyl-5-vinyl-9,10-dihydro-2,7-phenanthrenediol
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C18H18O2 | |
| Molar mass | 266.33 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Juncusol is a 9,10-dihydrophrenathrene found in Juncus species such as J. acutus,[1] J. effusus[2][3] or J. roemerianus.[4][5]
It can also be synthetized.[6][7][8]
This compound shows antimicrobial activity against Bacillus subtilis and Staphylococcus aureus.[4] It also has a toxic effect on estuarine fish and shrimp.[9]
References
- ^ Phenanthrenoids from Juncus acutus L., New Natural Lipopolysaccharide-Inducible Nitric Oxide Synthase Inhibitors. Fathi Abdelmohsen Abdelhalim Behery, Zain Elabdin Metwally Naeem, Galal Taha Maatooq, Mohamed Mahmoud Abdelfattah Amer, Zhi-Hong Wen, Jyh-Horng Sheu, Atallah Fouad Ahmed, Chemical and Pharmaceutical Bulletin, 2007, Vol. 55, No. 8, pages 1264-1266, doi:10.1248/cpb.55.1264
- ^ Bhattacharyya,Experientia,36,(1980),27
- ^ Shima,Phytochem.,30,(1991),3149
- ^ a b Antimicrobial activity of juncusol, a novel 9-10-dihydrophenanthrene from the marsh plant Juncus roemerianus. Kirit D. Chapatwala, Armando A. de la Cruz and D.Howard Miles, Life Sciences, 9 November 1981, Volume 29, Issue 19, Pages 1997–2001, doi:10.1016/0024-3205(81)90609-3
- ^ The structure of juncusol. A novel cytotoxic dihydrophenanthrene from the Estuarine marsh plant Juncus roemerianus. D H Miles, J Bhattacharyya, N V Mody, J L Atwood, S Black and P A Hedin, Journal of the American Chemical Society, February 1977, volume 99, issue 2, pages 618-620, PMID 830696
- ^ Total synthesis of juncusol. Edward McDonald and Roger T. Martin, Tetrahedron Letters, 1978, Volume 19, Issue 47, Pages 4723–4726, doi:10.1016/S0040-4039(01)85715-4
- ^ Regiospecific total synthesis of juncusol. Dale L. Boger and Michael D. Mullican, J. Org. Chem., 1984, volume 49, issue 21, pages 4045–4050, doi:10.1021/jo00195a034
- ^ A novel synthesis of juncusol. Peter A. Jacobi and Wanjun Zheng, Tetrahedron Letters, 4 March 1991, Volume 32, Issue 10, Pages 1279–1282, doi:10.1016/S0040-4039(00)79645-6
- ^ Toxic effects of juncusol a marsh plant phenolic extract on estuarine fish and shrimp. Chapatwala K.D, Life Sciences, 1982, volume 30, issue 21, pages 1805-1810, PMID 7098770