Juncusol

Juncusol
Names
IUPAC name
5-Ethenyl-1,6-dimethyl-9,10-dihydrophenanthrene-2,7-diol
Other names
1,6-Dimethyl-5-vinyl-9,10-dihydro-2,7-phenanthrenediol
Identifiers
62023-90-9
3D model (Jmol) Interactive image
ChemSpider 65579
PubChem 72740
Properties
C18H18O2
Molar mass 266.34 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 synthesized.[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

  1. ↑ Behery, Fathi Abdelmohsen Abdelhalim; Naeem, Zain Elabdin Metwally; Maatooq, Galal Taha; Amer, Mohamed Mahmoud Abdelfattah; Wen, Zhi-Hong; Sheu, Jyh-Horng; Ahmed, Atallah Fouad (2007). "Phenanthrenoids from Juncus acutus L., New Natural Lipopolysaccharide-Inducible Nitric Oxide Synthase Inhibitors". Chemical & Pharmaceutical Bulletin. 55 (8): 1264. doi:10.1248/cpb.55.1264.
  2. ↑ Bhattacharyya (1980). Experientia. 36: 27. Missing or empty |title= (help)
  3. ↑ Shima (1991). Phytochem. 30: 3149. Missing or empty |title= (help)
  4. 1 2 Chapatwala, Kirit D.; de la Cruz, Armando A.; Miles, D.Howard (1981). "Antimicrobial activity of juncusol, a novel 9-10-dihydrophenanthrene from the marsh plant". Life Sciences. 29 (19): 1997. doi:10.1016/0024-3205(81)90609-3. PMID 6796796.
  5. ↑ Miles, D. H.; Bhattacharyya, J; Mody, N. V.; Atwood, J. L.; Black, S; Hedin, P. A. (1977). "The structure of juncusol. A novel cytotoxic dihydrophenanthrene from the Estuarine marsh plant Juncus roemerianus". Journal of the American Chemical Society. 99 (2): 618–20. PMID 830696.
  6. ↑ McDonald, Edward; Martin, Roger T. (1978). "Total synthesis of juncusol". Tetrahedron Letters. 19 (47): 4723. doi:10.1016/S0040-4039(01)85715-4.
  7. ↑ Boger, Dale L.; Mullican, Michael D. (1984). "Regiospecific total synthesis of juncusol". The Journal of Organic Chemistry. 49 (21): 4045. doi:10.1021/jo00195a034.
  8. ↑ Jacobi, Peter A.; Zheng, Wanjun (1991). "A novel synthesis of juncusol". Tetrahedron Letters. 32 (10): 1279. doi:10.1016/S0040-4039(00)79645-6.
  9. ↑ de la Cruz, A. A.; Miles, D. H.; Chapatwala, K. D. (1982). "Toxic effects of juncusol, a marsh plant phenolic extract, on estuarine fish and shrimp". Life sciences. 30 (21): 1805–10. PMID 7098770.


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