Fragilin

Last updated
Fragilin
Fragilin.svg
Names
IUPAC name
2-Chloro-1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione
Other names
2-Chlorophyscion
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • 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
  • CC1=CC2=C(C(=C1)O)C(=O)C3=C(C(=C(C=C3C2=O)OC)Cl)O
Properties
C16H11ClO5
Molar mass 318.71 g·mol−1
Melting point 267–268 °C (513–514 °F; 540–541 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

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<span class="mw-page-title-main">Parietin</span> Chemical compound

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<span class="mw-page-title-main">Strepsilin</span> Lichen that contains strepsilin

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<span class="mw-page-title-main">Parietinic acid</span> Chemical compound found in some lichens

Parietinic acid is an organic compound in the structural class of chemicals known as anthraquinones. It is found in many species of the lichen family Teloschistaceae. The substance was first reported in the literature by the German chemist Walter Eschrich in 1958.

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<span class="mw-page-title-main">Fallacinol</span> Chemical compound found in some lichens

Fallacinol (teloschistin) is an organic compound in the structural class of chemicals known as anthraquinones. It is found in some lichens, particularly in the family Teloschistaceae, as well as a couple of plants and non lichen-forming fungi. In 1936, Japanese chemists isolated a pigment they named fallacin from the lichen Oxneria fallax, which was later refined and assigned a tentative structural formula; by 1949, Indian chemists had isolated a substance from Teloschistes flavicans with an identical structural formula to fallacin. Later research further separated fallacin into two distinct pigments, fallacin-A and fallacin-B (fallacinol). The latter compound is also known as teloschistin due to its structural match with the substance isolated earlier.

References

  1. 1 2 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.
  2. 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.
  3. 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.
  4. 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.