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Orchinol

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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
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,3-4H2,1-2H3Key: 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,3-4H2,1-2H3Key: HOVUVTNDNLNINP-UHFFFAOYAM
SMILES
  • COC1=CC(=C2C(=C1)CCC3=C2C=CC(=C3)O)OC
Properties
Chemical formula C16H16O3
Molar mass 256.301 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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

External links

Phenanthrenoids and their glycosides (molecules with a C6-C2-C6 backbone)
Phenanthrols
polyhydroxylated phenanthrenes
9,10-dihydrophenanthrene derivatives
glycosides
Phenanthrene glycosides
9,10-dihydrophenanthrene glycoside
dimeric phenanthrenes
Cyclic bibenzyl-dihydrophenanthrene derivative
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