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)	Interactive image;
ChEBI	CHEBI:144305;
ChemSpider	78436109;
PubChem CID	12443050;
	InChI 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;
	SMILES CC1=CC(=CC2=C1C3=C(O2)C=C(C4=C3COC4=O)O)O;
Properties
Chemical formula	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). Infobox references

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]

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

^ ^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.
^ Zopf, Wilhelm (4 April 1903). "Zur Kenntniss der Flechtenstoffe" (PDF). Justus Liebigs Annalen der Chemie. 327 (3): 317–354. doi:10.1002/jlac.19033270306.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.