Orchinol

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
  • 41060-20-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 158032
PubChem CID
  • 181686
UNII
  • V897GN013Q checkY
CompTox Dashboard (EPA)
  • DTXSID90961419 Edit this at Wikidata
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,3-4H2,1-2H3
    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
Chemical formula
 C16H16O3
Molar mass 256.301 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
Chemical compound

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]

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
  • Orchinol at kanaya.naist.jp/knapsack_jsp
  • Orchinol at WikiGenes
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Phenanthrenoids and their glycosides (molecules with a C6-C2-C6 backbone)
Phenanthrols
  • 1-Phenanthrol
  • 2-Phenanthrol
  • 3-Phenanthrol
  • 4-Phenanthrol
  • 9-Phenanthrol
polyhydroxylated phenanthrenes
  • 2,3,4-trimethoxy-7,8-methylenedioxyphenanthrene
  • 2,5-dihydroxy-3,4-dimethoxyphenanthrene
  • 2,5-dihydroxy-3,4,9-trimethoxyphenanthrene
  • 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
  • 2,7-dihydroxy-3,4,9-trimethoxyphenanthrene
  • 2,7-Dihydroxy-3,6-dimethoxyphenanthrene
  • 3-hydroxy-2,4,-dimethoxy-7,8-methylenedioxyphenanthrene
  • 2-hydroxy-3,5,7-trimethoxyphenanthrene
  • 2-hydroxy-3,5,7-trimethoxy-9,10-dihydrophenanthrene
  • 3,4,8-Trimethoxyphenanthrene-2,5-diol
  • 4,6-dimethoxyphenanthrene-2,3,7-triol
  • 4,9-dimethoxyphenanthrene-2,5-diol
  • 7-Hydroxy-2,3,4,8-tetramethoxyphenanthrene
9,10-dihydrophenanthrene derivatives
  • coelogin
  • coeloginin
  • coeloginanthridin
  • coelonin
  • effusol
  • hircinol
  • juncusol
  • loroglossol
  • orchinol
  • Plicatol C
  • 4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol
  • 4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol
  • 9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene
  • 9,10-dihydro-2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
  • 9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol
  • 9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene
glycosides
Phenanthrene glycosides
  • denneanoside A, B, C, D and E
9,10-dihydrophenanthrene glycoside
  • denneanoside F
dimeric phenanthrenes
  • cirrhopetalanthrin
  • flavanthrin
  • reptanthrin
  • isoreptanthrin
  • 8,8'-bidehydrojuncusol
Cyclic bibenzyl-dihydrophenanthrene derivative
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