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Lecanoric acid

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Lecanoric acid
Names
Preferred IUPAC name 4--2-hydroxy-6-methylbenzoic acid
Other names Orsellinate depside
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H14O7/c1-7-3-9(17)5-11(18)14(7)16(22)23-10-4-8(2)13(15(20)21)12(19)6-10/h3-6,17-19H,1-2H3,(H,20,21)Key: HEMSJKZDHNSSEW-UHFFFAOYSA-N
SMILES
  • CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)O)O)O)O
Properties
Chemical formula C16H14O7
Molar mass 318.281 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Lecanoric acid is a chemical produced by several species of lichen. Lecanoric acid is classified as a polyphenol and a didepside, and it functions as an antioxidant. It is an ester of orsellinic acid with itself.

The acid is named after the lichen Lecanora, in which it was discovered. The acid has also been isolated from Usnea subvacata, Parmotrema stuppuem, Parmotrema tinctorum, Parmotrema grayana, Xanthoparmelia arida and Xanthoparmelia lecanorica. A related compound, 5-chlorolecanoric acid, is found in some species of Punctelia.

References

  1. "Lecanoric acid". PubChem. National Center for Biotechnology Information. Retrieved 27 June 2019.
  2. Luo, Heng; Yamamoto, Yoshikazu; A Kim, Jung; Jung, Jae Sung; Koh, Young Jin; Hur, Jae-Seoun (13 March 2009). "Lecanoric acid, a secondary lichen substance with antioxidant properties from Umbilicaria antarctica in maritime Antarctica (King George Island)". Polar Biology. 32 (7): 1033–1040. Bibcode:2009PoBio..32.1033L. doi:10.1007/s00300-009-0602-9. S2CID 9256291.
  3. Hale, Mason E. (1990). A synopsis of the lichen genus Xanthoparmelia (Vainio) Hale (Ascomycotina, Parmeliaceae) /. Washington, D.C.: Smithsonian Institution Press. doi:10.5962/bhl.title.123253.
  4. White, Pollyanna; Oliveira, Rita; Oliveira, Aldeidia; Serafini, Mairim; Araújo, Adriano; Gelain, Daniel; Moreira, Jose; Almeida, Jackson; Quintans, Jullyana; Quintans-Junior, Lucindo; Santos, Marcio (12 September 2014). "Antioxidant Activity and Mechanisms of Action of Natural Compounds Isolated from Lichens: A Systematic Review". Molecules. 19 (9): 14496–14527. doi:10.3390/molecules190914496. PMC 6271897. PMID 25221871.
  5. Elix, John A.; Wardlaw, Judith H. (2002). "5-Chlorolecanoric acid, a new depside from Punctelia species" (PDF). Australasian Lichenology. 50: 6–9.
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