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Thamnolic acid

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Thamnolic acid
Names
IUPAC name 5-(3-carboxy-2-hydroxy-4-methoxy-6-methylbenzoyl)oxy-3-formyl-2,4-dihydroxy-6-methylbenzoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
InChI
  • InChI=1S/C19H16O11/c1-6-4-9(29-3)12(18(26)27)15(23)10(6)19(28)30-16-7(2)11(17(24)25)13(21)8(5-20)14(16)22/h4-5,21-23H,1-3H3,(H,24,25)(H,26,27)Key: RNCJCRJLNVRWJX-UHFFFAOYSA-N
SMILES
  • CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2C)C(=O)O)O)C=O)O)O)C(=O)O)OC
Properties
Chemical formula C19H16O11
Molar mass 420.326 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Thamnolic acid is a β-orcinol depside with the molecular formula C19H16O11. Thamnolic acid was first isolated from the lichen Thamnolia vermicularis, but it also occur in Cladonia species.

References

  1. ^ "Thamnolic acid". Pubchem.ncbi.NLM.nih.gov.
  2. Zeitschrift Für Naturforschung (in German). Dieterich'sche Verlagsbuchhandlung. 1967. p. 780.
  3. Elix, J. A.; Norfolk, S. (1975). "Synthesis of β-orcinol meta-depsides". Australian Journal of Chemistry. 28 (9): 2035–2041. doi:10.1071/ch9752035. ISSN 1445-0038.
  4. Bibliotheca lichenologica (in German). J. Cramer. 1973. p. 36. ISBN 978-3-443-58037-7.
  5. Der Stoffwechsel Sekundärer Pflanzenstoffe / The Metabolism of Secondary Plant Products. Springer Science & Business Media. 11 November 2013. p. 583. ISBN 978-3-662-26784-4.
  6. Brodo, Irwin M.; Sharnoff, Sylvia Duran; Sharnoff, Stephen; Nature, Canadian Museum of (1 January 2001). Lichens of North America. Yale University Press. p. 259. ISBN 978-0-300-08249-4.

Further reading

  • Linskens, H. F.; Tracey, M. V.; Beiss, Ulrich; Bendall, Fay; Björk, Walter; Bohlmann, F.; Boman, Hans G.; Braun, Richard; Heinen, W.; Hesse, Manfred; Hofmann, Eduard; Hudson, J. R.; Knapp, Rüdiger; Lambert, Rudolf; Miller, Carlos O.; Pfleiderer, Gerhard; Sanwal, B. D.; Schmid, Hans; Shibata, Shoji; Stern, Herbert; Sucrow, Wolfgang; Tobiška, Josef; Zilliken, F. W. (13 March 2013). Modern Methods of Plant Analysis / Moderne Methoden der Pflanzenanalyse. Springer-Verlag. p. 184. ISBN 978-3-642-94878-7.
  • Millot, M; Girardot, M; Dutreix, L; Imbert, C; Mambu, L (30 October 2014). "Lichen biodiversity: A source of secondary metabolites active against Candida biofilms". Planta Medica. 80 (16): s–0034–1394614. doi:10.1055/s-0034-1394614.
  • Asahina, Yasuhiko; Hiraiwa, Mitio (5 February 1936). "Untersuchungen über Flechtenstoffe, LXIV. Mitteil.: Über die Konstitution der Thamnolsäure (IV. Mitteil.)". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 69 (2): 330–333. doi:10.1002/cber.19360690220.
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