Orchinol

Orchinol is a 9,10-dihydrophenanthrene, a type of phenanthrenoid. It can be isolated from infected Orchis militaris and infected Loroglossum hircinum[1] with Rhizoctonia repens.[2] This molecule has a phytoalexin effect. It reduces the growth of Cattleya aurantiaca seedlings[3] and has an antifungal activity.[4]

Orchinol
Chemical structure of orchinol
Names
Preferred IUPAC name
5,7-Dimethoxy-9,10-dihydrophenanthren-2-ol
Other names
9,10-Dihydro-5,7-dimethoxyphenanthren-2-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C16H16O3/c1-18-13-8-11-4-3-10-7-12(17)5-6-14(10)16(11)15(9-13)19-2/h5-9,17H,3-4H2,1-2H3
    Key: HOVUVTNDNLNINP-UHFFFAOYSA-N
  • InChI=1/C16H16O3/c1-18-13-8-11-4-3-10-7-12(17)5-6-14(10)16(11)15(9-13)19-2/h5-9,17H,3-4H2,1-2H3
    Key: HOVUVTNDNLNINP-UHFFFAOYAM
  • COC1=CC(=C2C(=C1)CCC3=C2C=CC(=C3)O)OC
Properties
C16H16O3
Molar mass 256.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Structure of Orchinol, Loroglossol, and Hircinol. Roy M. Letcher and Llewellyn R. M. Nhamo, J. Chem. Soc., Perkin Trans. 1, 1973, pages 1263-1265, doi:10.1039/P19730001263
  2. Orchinol. Richard Braun, Moderne Methoden der Pflanzenanalyse, 1963, Volume 6, pages 130-134, doi:10.1007/978-3-642-94878-7_7 (article in German)
  3. Effects of Orchinol, Loroglossol, Dehydroorchinol, Batatasin III, and 3,4'- Dihydroxy-5-Methoxydihydrostilbene on Orchid Seedlings. Katherine A. Hills, Albert Stoessl, Allison P. Oliva and Joseph Arditti, Botanical Gazette, September 1984, Vol. 145, No. 3, pages 298-301 (link)
  4. Structure and antifungal activity of hircinol, loroglossol and orchinol. M.H. Fisch, Brigitta H. Flick and J. Arditti, Phytochemistry, February 1973, Volume 12, Issue 2, Pages 437–441, doi:10.1016/0031-9422(73)80036-6
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