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]

  1. ^ 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.