Chemistry:Lecanoric acid

From HandWiki
Lecanoric acid
Names
Preferred IUPAC name
4-[(2,4-Dihydroxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methylbenzoic acid
Other names
Orsellinate depside
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
Properties
C16H14O7
Molar mass 318.281 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Lecanoric acid is a chemical produced by several species of lichen.[1] Lecanoric acid is classified as a polyphenol and a didepside, and it functions as an antioxidant.[2] 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.[3][4] A related compound, 5-chlorolecanoric acid, is found in some species of Punctelia.[5]

References

  1. "Lecanoric acid". National Center for Biotechnology Information. https://pubchem.ncbi.nlm.nih.gov/compound/Lecanoric-acid. 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. doi:10.1007/s00300-009-0602-9. Bibcode2009PoBio..32.1033L. 
  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. http://dx.doi.org/10.5962/bhl.title.123253. 
  4. White, Pollyanna; Oliveira, Rita; Oliveira, Aldeidia; Serafini, Mairim; Araújo, Adriano; Gelain, Daniel; Moreira, Jose; Almeida, Jackson et al. (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. PMID 25221871. 
  5. Elix, John A.; Wardlaw, Judith H. (2002). "5-Chlorolecanoric acid, a new depside from Punctelia species". Australasian Lichenology 50: 6–9. https://www.anbg.gov.au/abrs/lichenlist/AL_50.pdf.