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Lobaric acid

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Lobaric acid
Names
IUPAC name 3-Hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzobenzodioxepine-2-carboxylic acid
Other names Lobraric acid; stereocaulic acid
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C25H28O8/c1-4-6-8-9-15-21(24(28)29)18(27)13-20-23(15)32-19-12-14(31-3)11-16(17(26)10-7-5-2)22(19)25(30)33-20/h11-13,27H,4-10H2,1-3H3,(H,28,29)Key: JHEWMLHQNRHTQX-UHFFFAOYSA-N
SMILES
  • CCCCCC1=C(C(=CC2=C1OC3=CC(=CC(=C3C(=O)O2)C(=O)CCCC)OC)O)C(=O)O
Properties
Chemical formula C25H28O8
Molar mass 456.491 g·mol
Melting point 196–198 °C (385–388 °F; 469–471 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Lobaric acid is a chemical compound with the molecular formula C25H28O8. It has been found in the Antarctic lichen Stereocaulon alpinum and a variety of other lichens. It is a member of the depsidone class of compounds.

A laboratory synthesis of lobaric acid has been reported.

References

  1. Morita, Hiroshi; Tsuchiya, Tomoe; Kishibe, Koji; Noya, Sayaka; Shiro, Motoo; Hirasawa, Yusuke (2009). "Antimitotic activity of lobaric acid and a new benzofuran, sakisacaulon a from Stereocaulon sasakii". Bioorganic & Medicinal Chemistry Letters. 19 (13): 3679–3681. doi:10.1016/j.bmcl.2009.03.170. PMID 19481447.
  2. Tian, Yuan; Li, Yan-Ling; Zhao, Feng-Chun (2017). "Secondary Metabolites from Polar Organisms". Marine Drugs. 15 (3): 28. doi:10.3390/md15030028. PMC 5367009. PMID 28241505.
  3. Kim, Tai Kyoung; Kim, Joung Eun; Youn, Ui Joung; Han, Se Jong; Kim, Il-Chan; Cho, Cheon-Gyu; Yim, Joung Han (2018). "Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum". Journal of Natural Products. 81 (6): 1460–1467. doi:10.1021/acs.jnatprod.8b00227. PMID 29878768.
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