Strepsilin

Strepsilin

Chemical structure of strepsilin

A crystal cluster of strepsilin; B single crystal
Names
IUPAC name
4,8-Dihydroxy-10-methyl-1H-[2]benzofuro[5,4-b][1]benzofuran-3-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C15H10O5/c1-6-2-7(16)3-10-12(6)14-8-5-19-15(18)13(8)9(17)4-11(14)20-10/h2-4,16-17H,5H2,1H3
    Key: OOXFLIUVCWLPKE-UHFFFAOYSA-N
  • CC1=CC(=CC2=C1C3=C(O2)C=C(C4=C3COC4=O)O)O
Properties
C15H10O5
Molar mass 270.24 g/mol
Melting point 324 °C (615 °F; 597 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Strepsilin is a chemical found in lichens. It produces an emerald green colour in the C test. It is a dibenzofuran dimer, with hydroxy, oxy and methyl side groups. It is named after Cladonia strepsilis.[1] Strepsilin was discovered by Wilhelm Zopf in 1903.[2][3] The structure of strepsilin was determined by Shoji Shibata.[4]

Properties

Strepsilin is degraded in alkali to 1-methyl-3,7-dihydroxydibenzofuran.[1]

Strepsilin melts at 324 °C.[1]

Occurrence

Cladonia strepsilis, the lichen that contains strepsilin

Strepsilin is found in some Cladonia species.[5] It is also found in Siphula[6] and Stereocaulon azoreum.[7]

References

  1. ^ a b c Shibata, Shoji (1957). "On the Structure of Strepsilin. II". Pharmaceutical Bulletin. 5 (5): 488–491. doi:10.1248/cpb1953.5.488. PMID 13505074.
  2. ^ Zopf, Wilhelm (4 April 1903). "Zur Kenntniss der Flechtenstoffe" (PDF). Justus Liebigs Annalen der Chemie. 327 (3): 317–354. doi:10.1002/jlac.19033270306.
  3. ^ Giles, Rgf; Sargent, Mv (1986). "Naturally-Occurring Dibenzofurans. X. A New Synthesis of Di-O-Methylstrepsilin". Australian Journal of Chemistry. 39 (12): 2177. doi:10.1071/CH9862177.
  4. ^ Brewer, J.D.; Elix, J.A. (January 1969). "The synthesis of di--methylstrepsilin". Tetrahedron Letters. 10 (47): 4139–4142. doi:10.1016/S0040-4039(01)88637-8.
  5. ^ Aptroot, André; Souza, Maria Fernanda; Spielmann, Adriano Afonso (2 July 2021). "Two New Crustose Cladonia Species with Strepsilin and Other New Lichens from the Serra de Maracaju, Mato Grosso do Sul, Brazil". Cryptogamie, Mycologie. 42 (8). doi:10.5252/cryptogamie-mycologie2021v42a8. S2CID 235769759.
  6. ^ Santesson, Johan (1967). "Chemical Studies on Lichens 6The Chemistry of the Genus Siphula II" (PDF). Acta Chemica Scandinavica. 21 (7): 1833–1837. doi:10.3891/acta.chem.scand.21-1833.
  7. ^ González, Antonio G.; Rodríguez Pérez, Elsa M.; Hernández Padrón, Consuelo E.; Barrera, Jaime Bermejo (1 August 1992). "Chemical Constituents of the Lichen Stereocaulon azoreum". Zeitschrift für Naturforschung C. 47 (7–8): 503–507. doi:10.1515/znc-1992-7-802. hdl:10261/18129. S2CID 13255580.