Fragilin

Fragilin
Names
	IUPAC name 2-Chloro-1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione
	Other names 2-Chlorophyscion
Identifiers
CAS Number	2026-19-9;
3D model (JSmol)	Interactive image;
PubChem CID	15559331;
UNII	5FI0O7S06V;
	InChI InChI=1S/C16H11ClO5/c1-6-3-7-11(9(18)4-6)15(20)12-8(14(7)19)5-10(22-2)13(17)16(12)21/h3-5,18,21H,1-2H3 Key: RTBAOFRCWWQFHB-UHFFFAOYSA-N;
	SMILES CC1=CC2=C(C(=C1)O)C(=O)C3=C(C(=C(C=C3C2=O)OC)Cl)O;
Properties
Chemical formula	C16H11ClO5
Molar mass	318.71 g·mol−1
Melting point	267–268 °C (513–514 °F; 540–541 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Fragilin is a chemical compound of the anthraquinone class. It has the molecular formula C₁₆H₁₁ClO₅ and is a chlorinated derivative of parietin. In 1965, it was reported as a constituent of the lichens Sphaerophorus fragilis and Sphaerophorus coralloides.^[1] It has since been found in a variety of other lichens including Nephroma laevigatum,^[2] Caloplaca,^[3] Xanthoria parietina,^[4] and others.

References

^ ^a ^b Bruun, Torger; Hollis, Donald P.; Ryhage, Ragnar; Nielsen, P. H.; Sjöberg, Berndt; Larsen, Erik (1965). "The Constitution of Fragilin". Acta Chemica Scandinavica. 19: 839–844. doi:10.3891/acta.chem.scand.19-0839.
^ Bendz, Gerd; Bohman, Gerd; Santesson, Johan; Cyvin, S. J.; Hagen, G. (1967). "Chemical Studies on Lichens. 9. Chlorinated Anthraquinones from Nephroma laevigatum". Acta Chemica Scandinavica. 21: 2889–2890. doi:10.3891/acta.chem.scand.21-2889.
^ Bohman, Gerd (1969). "Anthraquinones from the genus Caloplaca". Phytochemistry. 8 (9): 1829–1830. Bibcode:1969PChem...8.1829B. doi:10.1016/s0031-9422(00)85978-6.
^ Sargent, M. V.; Smith, David O'N.; Elix, J. A. (1970). "The minor anthraquinones of Xanthoria parietina(L.) Beltram, the chlorination of parietin, and the synthesis of fragilin and 7-chloroemodin ('AO-1')". J. Chem. Soc. C (2): 307–311. doi:10.1039/J39700000307.